Abstract
Being relatively simple compounds, 2,5-dioxopiperazines are amongst the most ubiquitous peptide derivatives found in nature. Hydrolysates of proteins and polypeptides often contain these anhydro-dimers of amino-acids and they are commonly isolated from cultures of yeast, lichens and fungi. Their existence as a special group of compounds was first recognized around 1900 (1). The great Emil Fischer managed to synthesize many of the simpler members of this family in the early 1900’s (2). The parent compound, 2,5-dioxopiperazine, often referred to as cyclo-gly-gly*, was made in 1888 (3).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Fischer, E., and K. Raske: Beitrag zur Stereochemie der 2,5-Diketopiperazine. Ber. 39, 3981 (1906).
Fischer, E.: Untersuchungen über Aminosäuren, Polypeptide und Proteine. Ber. 39, 530 (1906).
Curttus, T., and Goebel: J. prakt. Chem. 37, 173 (1888).
Abderhalden, E., and E. Komm: The Formation of Diketopiperazines from Polypeptides Under Various Conditions. Z. physiol. Chem. 139, 147 (1924).
Abderhalden, E., and R. Haas: Further Studies on the Structure of Proteins: Studies on the Physical and Chemical Properties of 2,5-Diketopiperazines. Z. physiol. Chem. 151, 114 (1926).
Katchalski, E., I. Grossfield, and F. M. Frankel: Synthesis of Lysine Anhydride. J. Am. Chem. Soc. 68, 879 (1946).
Kopple, K. D., and D. H. Marr: Conformations of Cyclic Dipeptides: The Folding of Cyclic Dipeptides containing an Aromatic Side Chain. J. Am. Chem. Soc. 89, 6193 (1967).
Greenfield, N. J., and G. D. Fasman: Optical Activity of Simple Cyclic Amides in Solution. Biopolymers 7, 595 (1969).
Balasubramanian, D., and D. B. Wetlaufer: Optical Rotatory Properties of Diketopiperazines. J. Am. Chem. Soc. 88, 3449 (1966).
Schellman, J. A., and B. E. Nielson: In “Conformations of Biopolymers”, ed. G. N. Ramachandran, vol. 1, p. 109. New York: Academic Press. 1967.
Edelhoch, H., R. E. Lippoldt, and M. Wilcheck: The Circular Dichroism of Tyrosyl and Tryptophanyl Diketopiperazines. J. Biol. Chem. 243, 4799 (1968).
Bellamy, L. J.: The Infrared Spectra of Complex Molecules. Chapter 12. London: Methuen and Co. Ltd. 1957.
Blaha, K., J. Smolfxova, and A. Vitek: Aminoacids and Peptides, LXIV. Infrared Spectra of Substituted 2,5-Piperazinediones and the Detection of cis-Peptide Bonds in Diastereoisomeric Cyclohexapeptides. Coll. Czech. Chem. Commun. 31, 4296 (1966).
Jankowsky, K., and L. Varfalvy: Mass Spectroscopy of 2,5-Dioxopiperazines. II. A Study of cyclo-Ala-ala. Bull. Acad. Pol. Sci. Ser. Sci. Chim. 20, 493 (1966).
Svec, H. J., and G. A. June: The Mass Spectra of Dipeptides. J. Am. Chem. Soc. 86, 2278 (1964).
Nagarajan, R., J. L. Occolowitz, N. Neuss, and S. M. Nash: Mass Spectra of Diketopiperazines from Aranotin and Related Metabolites. Chem. Commun. 1969, 359.
Romanet, R., A. Chemizard, S. Duhoux, and S. David: Etudes par resonance magnetique nucleaire de l’echinuline, de certains derives et de modeles indoliques. Bull. soc. Chim. France 1048 (1963).
Chemizard, A., and S. David: Remarques sur les dioxo-2,5-piperazines. Bull. soc. Chim. France 1966, 184.
Kopple, K. D., and M. Ohnishi: Conformations of Cyclic Peptides II: Side-chain Conformation and Ring Shape in Cyclic Dipeptides. J. Am. Chem. Soc. 91, 962 (1969).
Young, P. E., V. Madison, and E. R. Blout: Cyclic Peptides VI. Europium Assisted N. M. R. Study of the Solution Conformation of cyclo (L-pro-L-pro) and cyclo (L-proD-pro). J. Am. Chem. Soc. 95, 6142 (1973).
Krezcarek, G. E., B. W. Dominy, and R. G. Lawton: The Interaction of Reactive Functional Groups along Peptide Chains: A Model for Alkaloid Biosynthesis. Chem. Commun. 1968, 1450.
Fischer, E.: Syntheses von Polypeptiden, XV. Ber. 39, 2893 (1906).
Blaha, K.: Amino-acids and Peptides, XCV. Synthesis of Some Diastereoisomeric 2,5-Piperazine-diones. Coll. Czech. Chem. Commun. 34, 4000 (1969).
Nitecki, D. E., B. Halpern, and J. W. Westley: A Simple Route to Sterically Pure Diketopiperazines. J. Org. Chem. 33, 864 (1968).
Schott, H. F., J. B. Larkin, L. B. Rockland, and M. S. Dunn: The Synthesis of 1 (−) Leucylglycylglycine. J. Org. Chem. 12, 490 (1947).
Rosenmund, P., and K. Kains: Diketopiperazines from Leuchs’ Anhydrides. Angew. Chem. Internat. Edn. 9, 162 (1970).
Kopple, K. D., and H. G. Ghazarian: A Convenient Synthesis of 2,5-Dioxopiperazines. J. Org. Chem. 33, 862 (1968).
Lichtenstein, N.: The Behaviour of Dipeptides when Heated in 13-Naphthol. J. Am. Chem. Soc. 60, 560 (1938).
Zahn, H., and D. Brandenburg: Synthese einer geschützten Heptapeptidsequenz aus dem Tyrocidin B. Annalen 692, 220 (1966).
Grahl-Nielson, O.: Acid Hydrolysis of Diastereoisomeric Dioxopiperazines. Tetrahedron Letters 1969, 2827.
Slater, G. P.: Synthesis of Piperazine-2,5-diones. Chem. & Ind. (London) 1969, 1092.
Goodman, M., and K. C. Steuben: Peptide Synthesis via Aminoacid Esters, II. Some Abnormal Reactions during Peptide Synthesis. J. Am. Chem. Soc. 84, 1279 (1962).
Westley, J. W., V. A. Close, D. E. Nitecki, and B. Halpern: Determination of Steric Purity and Configuration of Diketopiperazines by Gas-liquid Chromatography, Thin-layer chromatography and Nuclear Magnetic Resonance Spectrometry. Anal. Chem. 40, 1888 (1968).
Tsusoi, M., T. Shimanouchi, and S. Miyushima: Near Infrared Spectra of Compounds with Two Peptide Bonds and the Configuration of a Polypeptide Chain, VII. On the Extended Form of Polypeptide Chains. J. Am. Chem. Soc. 81, 1406 (1959).
Indelicato, T. M., T. T. Norvilas, and W. J. Wheeler: Intramolecular Nucleophilic Attack in 7 (α-Amino) phenylcephalosporanic Esters. J. C. S. Chem. Commun. 1972, 1162.
Roets, E. R., A. J. Vlietnieck, G. A. Janssen, and H. Vanderhaeghe: IntramolecUlar Nucleophilic Attack in 6-Epiampicillin. J. C. S. Chem. Commun. 484 (1973).
Titlestad, K.: Cleavage of Linear Tetrapeptides into Two Cyclic Dipeptides. Chem. Commun. 1971, 1527.
Lucente, G., and P. Frattesi: Cyclisation of Activated Tosyl-peptides. Tetrahedron Letters 1972, 4283.
Mauger, A. B.: Degradation of Peptides to Diketopiperazines: Applications of Pyrolysis-Gas Chromatography to Sequence Determination in Actinomycins. Chem. Commun. 1971, 39.
Poisel, H., and U. Schmidt: Asymmetrische Induktion bis Reaktionen von Aminosäuren und Peptiden, I. Asymmetrische Synthese Aromatische α-Aminosäuren und N-Methyl α-Aminosäuren. Synthese von L-DOPA. Über die Katalytische Hydrierung ungesättigter Cyclopeptide. Chem. Ber. 106, 3408 (1973).
Degeilh, R., and R. E. Marsh: A Refinement of the Crystal Structure of Diketopiperazine (2,5-Piperazine-dione). Acta Crystallog. 12, 1007 (1959).
Benedetti, E., P. Corradini, and C. Pedone: Crystal and Molecular Structure of L-cis-3,6-Dimethyl-2,5-piperazinedione (L-alanyl-L-alanine-2,5-diketopiperazine). Bio-polymers 7, 751 (1969).
Benedetti, E., P. Corradini, and C. Pedone: The Crystal and Molecular Structure of trans-3,6-Dimethyl-2,5-piperazinedione. J. Phys. Chem. 73, 2891 (1969).
Sletten, E.: Conformation of Cyclic Dipeptides: The Crystal and Molecular Structures of Cyclo-D-alanyl-L-alanyl and cyclo-L-Alanyl-L-alanyl. J. Am. Chem. Soc. 92, 172 (1970).
Benedetti, E., P. Corradini, M. Goodman, and C. Pedone: Flexibility of Supposed “Rigid” Molecules: Substituted 2,5-Piperazinediones (Diketopiperazines). Proc. Natn. Acad. Sci. USA, 62, 650 (1969).
Groth, P.: Crystal Structure of N,N’-Dimethyldioxopiperazine. Acta Chem. Scand. 23, 3155 (1969).
Karle, I. L.: Crystal Structure and Conformation of the Cyclic Dipeptide, cyclo-LProlyl-L-leucyl. J. Am. Chem. Soc. 94, 81 (1972).
Siemion, I. Z.: Die Konformation des Prolin Ringes in Diketopiperazin Systemen. Annalen 748, 88 (1971).
Siemion, I. Z.: NMR Investigation of Proline Containing Dioxopiperazines. Org. Magn. Resonance 3, 545 (1971).
Blaha, K., M. Bodesinsky, I. Fric, J. Smoukona, and J. Vicar: Cyclodipeptides. Conformational Analysis and Spectroscopic Studies. Tetrahedron Letters 1972, 4437.
Gawne, G., G. W. Kenner, N. H. Rogers, R. C. Sheppard, and K. Titlestad: In “Peptides”, ed. E. Brlcas, p. 28. Amsterdam: North-Holland Publishing Co. 1968.
Ziauddin, K. D. Kopple, and C. A. Bush: Conformations of cyclo-L-His-L-Ser, cyclo-L-His-L-Asp, and cyclo-L-His-L-His. Tetrahedron Letters 1972, 483.
cf. Johnson, C. E., and F. A. Bovey: Calculation of Nuclear Magnetic Resonance Spectra of Aromatic Hydrocarbons. J. Chem. Phys. 29, 1012 (1958).
Ziauddin, and K. D. Kopple: Conformations of Folded Peptides: Stabilities of Folded Conformations of para-substituted 3-Benzylpiperazine-2,5-diones. J. Org. Chem. 35, 253 (1970).
Caillet, J., B. Pullmann, and B. Maigret: Molecular Orbital Calculations On the Folding of Cyclic Dipeptides with Aromatic and Aliphatic Side Chains. Biopolymers 10, 221 (1971).
Kopple, K. D., R. R. Jarabak, and P. L. Muller: Reactivity of Cyclic Peptides. III. Reaction of Isomeric Histidine, Tyrosine Peptides with p-Nitrophenyl Acetate. Biochem. 2, 958 (1963).
Zbiral, E., E. L. Menard, and J. M. Muller: über die Inhaltsstoffe von Zizyphus oenoplia Mill. II. Zur Konstitutionsmittlung des Zizyphins. Helv. Chim. Acta 48, 1608 (1965).
Pailer, M., E. Haslinger, and E. Zbiral: Zur Konstitution des Zizyphinins von Zizyphus oenoplia Mill. Monatsh. Chem. 100, 1608 (1968).
Warnhoff, E. W.: Peptide Alakoids. Fortschr. Chem. Organ. Naturstoffe 28, 162 (1970).
Bodansky, M., G. F. Singler, and A. Bodansky: Structure of the Peptide Antibiotic Amphomycin. J. Am. Chem. Soc. 95, 2352 (1973).
Arison, B. H., and J. L. Beck: The Structure of Compound 593 A, A New Anti-tumor Agent. Tetrahedron 29, 2743 (1973).
Forster, M. O., and W. B. Saville: Isolation of Picroroccellin from Rocella fuciformis. J. Chem. Soc. 121, 816 (1922).
Atkins, C. L., and J. B. Neilands: Rhodotorulic Acid. A Diketopiperazine Dihydroxamic Acid with Growth Regulatory Properties. I. Isolation and Characterization. Biochem. 7, 3734 (1968).
Keller-Schierlein, W., V. Prelog, and H. Zahner: Siderochrome. Fortschr. Chem. Organ. Naturstoffe 22, 279 (1964).
Akers, H. A., M. Llinas, and J. B. Neilands: Protonated Amino Acid Studies on Rhodotorulic Acid Biosynthesis in D2O Media. Biochem. 11, 2283 (1972).
Isowa, Y. T., Takashima, M. Ohmori, H. Kurita, M. Sato and K. Mori, Synthesis of Rhodotorulic Acid. Bull Chem. Soc. Japan 45, 1467 (1972).
Diekmann, H.: Metabolic Products of Microorganism. Part 81. Occurrence and Structure of Coprogen B and Dimerumic Acid. Arch. Mikrobiol. 73, 65 (1970).
Keller-Schierlein, W., and H. Diekmann: Zur Konstitution des Coprogens. Helv. Chim. Acta 53, 2035 (1970).
Hedy, P. H., E. B. Hodge, V. V. Young, R. L. Harried, G. A. Brewer, W. F. Phillips, W. F. Runge, H. E. Stavely, A. Pohland, H. Boaz, and H. R. Sullivan: Structure and Reactions of Cycloserine. J. Am. Chem. Soc. 77, 2345 (1955).
Karpeiskii, M. Yu., Yu. N. Breusov, R. M. Khomatov, E. S. Severin, and O. C. Polyanovskii: The Mechanism of Action of Cycloserine and Related Compounds with Aspartic-Glutamic Transaminase. Biokhimiya 28, 342 (1963). Chem. Abs. 59, 4219 f (1963).
Lassen, F. O., and C. H. Stammer: Cycloserine Dimer Hydrolysis and its Equilibration with Cycloserine. J. Org. Chem. 36, 2631 (1971).
Miller, J. C., F. C. Neuhaus, F. O. Lassen, and C. H. Stammer: The Reactions of 3,6-Bis(aminoxymethyl)-2,5-piperazinedione with Acid and Alkali. A Kinetic Study. J. Org. Chem. 33, 3908 (1968).
Poduska, K., G. S. Katrukha, A. B. Silaev, and J. Rudinger: Amino Acids and Peptides. LII. Intramolecular Aminolysis of Amide Bonds in Derivatives of αγ-Diaminobutyric Acid, αβ-Diaminopropionic Acid, and Ornithine. Coll. Czech. Chem. Commun. 30, 2410 (1965).
Mckinney, J. D., and C. H. Stammer: Role of Azomethines in the Dimerisation of Cycloserine by Aldehydes. Tetrahedron 25, 163 (1969).
Wrinch, D.: The Cyclol Theory in the “Globular” proteins. Nature 139, 972 (1969).
Wrinch, D.: Chemical Aspects of Polypeptide Chain Structures and the Cyclol Theory. Copenhagen: Munksgaard. 1956.
Shemyakin, M. M., V. K. Antonov, A. M. Shkrob, V. I. Shchelekov, and Z. E. Agadzhanyan: Activation of the Amide Group by Acylation. Tetrahedron 21, 3537 (1965).
Shemyakin, M. M., Y. A. Ovchimichov, V. K. Antonov, A. A. Kiryashkin, V. I. Ivanov, V. I. Shchelekov, A. M. Shkrob: Total Synthesis of Serratamolide, I. Synthesis of O,O’-Diacetyl Serratamolide. Tetrahedron Letters 1964, 47.
Stoll, A.: Recent Investigations on Ergot Alkaloids. Fortschr. Chem. Organ. Naturstoffe 9, 114 (1952).
Hofmann, A., A. J. Frey, and H. Ott: Die Totalsynthese des Ergotamins. Experientia 17, 206 (1961).
Rothe, M., and R. Steinberger: Thiocyclols and Cyclothio-depsipeptides. Angew. Chem., Internat. Edn. 7, 884 (1968).
Rothe, M., T. Tothe, and D. Jacob: Synthesis of an Azacyclol. Angew. Chem., Internat. Edn., 10, 128 (1971).
Stoll, A., and Hofmann: The Ergot Alkaloids in “The Alkaloids”, ed. R. F. Manske, Vol. 8, p. 725. New York: Academic Press. 1965.
Leonard, N. J.: Transannular Nitrogen-Carbonyl Interactions. Record Chem. Progress 17, 243 (1956).
Lucente, G., and A. Romeo: Synthesis of Cyclols from some small Peptides via Amide-Amide Reaction. Chem. Commun. 1971, 1605.
Cerrini, S., W. Fedeli, and F. Mazza: X-Ray Crystallographic Proof of a Cyclol Structure in a Tripeptide. Chem. Commun. 1971, 1607.
Machin, P. J., and P. G. Sammes: Unpublished work.
Simonson, L. A., and C. K. Mann: Anodically Induced 1,3-Cyclo addition of Acetonitrile to 3,6-Diisobutylpiperazine-2,5-dione. Tetrahedron Letters 1970, 3303.
Blake, K. W., and P. G. Sammes: Geometrical Isomerism and Tautomerism of 3-Arylidene-6-methylpiperazine-2,5-diones. J. Chem. Soc. (C) 1970 (980).
Machin, P. J., A. E. A. Porter, and P. G. Sammes: Pyrazine Chemistry. Part V. Diels-Alder Reactions of Some 2,5-Dihydroxypyrazines. J. C. S., Perkin I, 1973, 404.
Bergmann, M., and A. Miekeley: Neue Desmotrope Aminosäureanhydride von Piperazintypus. Zur Kenntnis des Abbau der Aminosäuren. Serine als Dehydrierungsmittel. Annalen 458, 40 (1927).
Chakrabartty, S. K., and R. Levine: Chemistry of Pyrazine and its Derivatives. XII. Reaction of Acetonylpyrazine with Phenyllithium in the Presence and Absence of Methyl Benzoate. J. Heterocyclic Chem. 4, 109 (1967).
Khokrov, A. S., and G. B. Losxkin: The Structure of Albonoursin. Tetrahedron Letters 1963, 1881.
Shin, C., Y. Chigera, M. Masaki, and A. Ohta: Total Synthesis of Albonoursin. Tetrahedron Letters 1967, 4601.
Gallina, C., and A. Liberatori: A New Synthesis of 1-Acetyl-3-Arylidene (alkylidene)piperazine-2,5-diones. Tetrahedron Letters 1973, 1135.
Shin, C., Y. Chigera, M. Masaki, and A. Ohta: Synthesis of Albonoursin. Bull. Chem. Soc. Japan 42, 191 (1969).
Porter, A. E. A., and P. G. Sammes: On the Synthesis of 3-Benzylidenepiperazine2,5-diones. J. Chem. Soc. C 1970, 2530.
Sheehan, J. C., D. Mania, S. Nakamura, J. A. Stock, and K. Maeda: The Structure of Telomycin. J. Am. Chem. Soc. 90, 462 (1968).
Shin, C., M. Masaki, and A. Ohta: The Independent Isolation of a Primary Enamine and the Tautomeric Imine. Bull. Chem. Soc. Japan 44, 1657 (1971).
Quilico, A., and L. Panizzi: Chemische Untersuchungen über Aspergillus echinulatus. I. Mitteilung. Ber. 76, 348 (1943).
Quiuco, A.: The Constitution of Echinulin. Res. Progr. org. biol. med. Chem. 1, 225 (1964).
Birch, A. J., G. E. Blance, S. David, and H. Smith: Studies in relation to Biosynthesis. Part XXIV. Some Remarks on the Structure of Echinulin. J. Chem. Soc. 1961, 3128.
Macdonald, J. C., and G. P. Slater: The Utilization of Tryptophan in the Biosynthesis of Echinulin. Canad. J. Microbiol.12, 455 (1966).
Slater, G. P., J. C. MacDonald, and R. Nakashima: Biosynthesis of Echinulin by Aspergillus amstelodami from Cyclo-L-alanyl-L-tryptophanyl-14C. Biochem. 9, 2886 (1970).
Nakashima, R., and G. P. Slater: Configuration of Echinulin II. Optical Rotatory Dispersion of Echinulin, Hydroechinulin, and the Stereoisomeric 3-Methyl-6-(indolyl3-methyl)piperazine-2,5-diones. Canad. J. Chem. 47, 2069 (1969).
Houghton, E., and J. E. Saxton: The Echinulins: Preliminary Synthetic Studies and the Absolute Configuration of Echinulin. Tetrahedron Letters 1968, 5475.
Birch, A. J., and K. R. Farrar: Studies in Relation to Biosynthesis. Part XXXIII. Incorporation of Tryptophan into Echinulin. J. Chem. Soc. 1963, 4277.
Jackson, A. H., and A. E. Smith: Electrophilic Substitution in Indoles I. Model Experiments Related to the Synthesis of Echinulin. Tetrahedron 21, 989 (1965).
Casnati, G., M. Francioni, A. Guareschi, and A. Pochini: Insertion of Isoprene Units into Indole Systems. Tetrahedron Letters 1969, 2485.
Casnati, G., and A. Pochini: Rearrangement of 3-Alkyl-l-allylindoles; A Model Reaction for the Biogenesis of Echinulin-type Compounds. Chem. Commun. 1970, 1328.
Dix, D. T., J. Martin, and C. E. Moppett: Molecular Structure of the Metabolite Lanosulin. J. C. S. Chem. Commun. 1972, 1168.
Bycroft, B. W., and W. Landon: Thio-Claisen Rearrangements of Sulphonium Salts: Implications in Indole Alkaloid Biosynthesis. Chem. Commun. 1970, 967.
Plieninger, H., and H. Herzog: Synthesis of O- and C-Alkylated Indoxyl Derivatives. Preliminary work for the Synthesis of Echinulin. Monatsh. Chem. 98, 807 (1967).
Houghton, E., and J. E. Saxton: Echinulin Series. Part II. Synthesis of ± Alanyltryptophan Anhydride and L-Alanyl-2-(1,1-dimethyl)allyltryptophan Anhydride. J. Chem. Soc. (C) 1969, 1003.
Takamatsu, N., S. Indue, and Y. Kishi: Synthetic Study on Echinulin and Related Compounds. Part II. A Stereoselective Total Synthesis of Optically Active Echinulin. Tetrahedron Letters 1971, 4665.
Takamatsu, N., S. Inoue, and Y. Kishi: Synthetic Study on Echinulin and Related Compounds. Part I. Acid-catalyzed Amino-Claisen Rearrangement of allyl-and 3,3-Dimethylallyl Aniline Derivatives. Tetrahedron Letters 1971, 4661.
Kishi, Y., S. Nakatsuku, T. Fukuyama, and T. Goto: A Stereoselective Decarboxylation of 1,6-Dimethyl-3(3’-indolyl)methyl-3-carboxy-2,5-piperazinedione. Tetrahedron Letters 1971, 4657.
Allen, C. M.: Biosynthesis of Echinulin. Isoprenylation of Cyclo-L-alanyl-Ltryptophanyl. Biochem. 11, 2154 (1972).
Allen, C. M.: Monoisoprenylated Cyclo-L-ala-L-try as a Biosynthetic Precursor of Echinulin. J. Am. Chem. Soc. 95, 2386 (1973).
Barbetta, M., G. Casnati, A. Pochini, and A. Silva: Neoechinulin — a New Indole Metabolite from Aspergillus echinulatus. Tetrahedron Letters 1967, 4457.
Casnati, G., A. Pochini, and R. Ungaro: Neoechinulin: A New Isoprenylindole Metabolite from Aspergillus amstelodami. Gazz. Chim. Ital., 103, 141 (1973).
Birch, A. J., and J. J. Wright: The Brevianamides: A New Class of Fungal Alkaloid. Chem. Commun. 1969, 644.
Birch, A. J., and J. J. Wright: Studies in Relation to Biosynthesis. Part XLII. The Structural Elucidation and some Aspects of the Biosynthesis of the Brevianamides A and E. Tetrahedron 26, 2329 (1970).
Birch, A. J., and R. A. Russell: Studies in Relation to Biosynthesis. Part XLIV. Structural Elucidations of Brevianamides B, C, D, and F. Tetrahedron 28, 2999 (1972).
Steyn, P. S.: Austamide: A New Toxic Metabolite from Aspergillus ustus. Tetrahedron Letters 1971, 3331.
Steyn, P. S.: The Structures of Five Diketopiperazines from Aspergillus ustus. Tetrahedron 29, 107 (1973).
cf. Gilbert, B.: The Alkaloids of Aspidosperma and Related Genera, in “The Alkaloids”, ed. R. H. F. Manske, p. 335. New York: Academic Press. 1965.
Witkop, B., and J. B. Patrick: The Course and Kinetics of the Acid-Base Catalyzed Rearrangements of 11-Hydroxytetrahydrocarbazolenine. J. Am. Chem. Soc. 73, 2188 (1951).
Neuss, N., R. Nagarajan, B. B. Molloy, and L. L. Huckstep: Aranotin and Related Metabolites II. Isolation, Characterization and Structure of Two New Metabolites. Tetrahedron Letters 1968, 4467.
Coetzer, J., and P. S. Steyn: The Crystal Structure of 5-Bromo-12S-tetrahydroaustamide. Acta Cryst. B29, 685 (1973).
Srinivasan, R.: Photochemistry of Cyclic Ketones. Adv. Photochem. 1, 83 (1963).
Porter, A. E. A., and P. G. Sammes: A Diels-Alder Reaction of Possible Biosynthetic Importance. Chem. Commun. 1970, 1103.
Yamazaki, A. S. Suzuki, and K. Mizaki: Tremorgenic Toxins from Aspergillus fumigatus Fres. Chem. Pharm. Bull. (Japan) 19, 1739 (1971).
The author thanks Professor A. Yamazaki, Institute of Food Microbiology, Chiba University, Japan, for this information. Details of the revised structure for lanosulin were revealed at the IUPAC Congress, Hamburg, September, 1973.
The Author is indebted to Professor J. Clardy, Ames Laboratory, Iowa State University, U.S.A., for the details of the X-ray analysis of verruculogen before its publication.
Clarke, H. J., J. R. Johnson, and R. Robinson: The Chemistry of Penicillin, Princeton University Press, 1949.
White, E. C.: Bactericidal Filtrates from a Mould Culture. Science 92, 127 (1940).
White, E. C., and J. H. Hill: Studies on Antibacterial Products Formed from Moulds. I. Aspergillic Acid. A Product of a Strain of Aspergillus flavus. J. Bacteriol. 45, 433 (1943).
Newbold, G. T., W. Sharp, and F. S. Spring: Aspergillic Acid. Part III. The Synthesis of Racemic Deoxyaspergillic Acid. J. Chem. Soc. 1951, 2679.
Dunn, G., G. T. Newbold, and F. S. Spring: Synthesis of Flavacol, a Metabolic Product of Aspergillic flavus. J. Chem. Soc. 1949, 2586.
Nakamura, S.: Structure of Muta-aspergillic Acid. Agr. Biol. Chem. (Tokyo) 25, 74 (1961).
Masaki, M., Y. Chigura, and M. Ohta: Total Synthesis of Racemic Aspergillic Acid and Neoaspergillic Acid. J. Org. Chem. 31, 4143 (1966).
Masaki, M., and M. Ohta: Synthesis of a Homologue of Aspergillic Acid. J. Org. Chem. 29, 3165 (1964).
Sugiyama, M., Masaki, and M. Ohta: Synthesis of 1-Hydroxy-6-(1-hydroxy-lmethylethyl)-2-pyraxinone and the Structure of Muta-aspergillic Acid. Tetrahedron Letters 1967, 845.
Ohta, A., and S. Futii: Synthesis of DL-Aspergillic Acid and DL-Deoxyaspergillic Acid. Chem. Pharm. Bull. (Japan) 17, 851 (1969).
Ohta, A.: Synthesis of Neoaspergillic Acid. Chem. Pharm. Bull. (Japan) 16, 1160 (1968).
Macdonald, J. C.: in: The Antibiotics, Vol. II. Biosynthesis, ed. D. Gottlieband P. D. Shaw, p. 43. New York: Springer. 1967.
Micetich, R. G., and J. C. Macdonald: Metabolities from Aspergillus sclerotiorum Huber. J. Chem. Soc. 1964, 1507.
Macdonald, J. C.: Biosynthesis of Aspergillic Acid. J. Biol. Chem. 236, 512 (1961).
Macdonald, J. C.: Biosynthesis of Hydroxyaspergillic Acid. J. Biol. Chem. 237, 1977 (1962).
Cook, A. H., and C. A. Slater: The Structure of Pulcherrimin. J. Chem. Soc. 1956, 4133.
Kluyver, A. J., J. P. Ven Der Walt, and A. J. Can Triet: Pulcherrimin, the Pìzment of Candida pulcherrimin. Proc. Natl. Acad. Sci. U.S. 39, 583 (1953).
Macdonald, J. C.: The Biosynthesis of Pulcherriminic Acid. Biochem. J. 96, 533 (1965).
Macdonald, J. C.: The Structure of Pulcherriminic Acid. Canad. J. Chem. 41, 165 (1963).
Dutcher, J. D.: Aspergillic Acid. An Antibiotic Substance from Aspergillus flavus. J. Biol. Chem. 171, 321 (1947).
Bates, R. B., J. H. Schauble, and M. Soucek: The C10H17 Side Chain in Mycelianamide. The Stereochemistry of Bergamottin and Umbelliprenin. Tetrahedron Letters 1963, 1683.
Ohta, A.: Synthesis of Pulcherrimin and Pulcherriminic Acid. Chem. Pharm. Bull. (Japan) 12, 125 (1964).
Oxford, A. E., and H. Raistrick: Studies on the Biochemistry of Microorganisms. Part 76. Mycelianamide. Biochem. J. 43, 323 (1948).
Birch, A. J., L. A. Massey-Westropp, and R. W. Rickards: Studies Related to Biosynthesis. Part VIII. The Structure of Mycelianamide. J. Chem. Soc. 1956, 3717.
Gallina, C., A. Romeo, V. Tortorella, and G. D’Agnelo: Synthesis of Racemic Deoxymycelianamide. Chem. & Ind. (London) 1966, 1300.
Bapat, J. B., D. St. C. Black, and R. F. C. Brown: Cyclic Hydroxamic Acids. Adv. Heterocyclic Chem. 10, 199 (1969).
Brown, R. F. C., and G. C. Meehan: Synthetic Approaches to Mycelianamide. Austral. J. Chem. 21, 1581 (1968).
Teranishi, R.: Odor and Molecular Structure, in “Gustation and Olfaction”, ed. G. Ohloffand A. F. Thomas, p. 165. New York: Academic Press. 1971.
Seifert, R. M., R. G. Buttery, D. G. Guadagin, D. R. Black, and J. G. Harris: Synthesis of some 2-Methoxy-3-alkylpyrazines with strong Bell-pepper like Odours. J. Agr. Food Chem. 18, 246 (1970).
Murray, K. E., J. Shipton, and F. B. Whitfield: 2-Methoxypyrazines and the Flavour of Green Peas (Pisum sativum). Chem. & Ind. (London) 1970, 897.
Weindling, R., and O. Emerson: Isolation of a Toxic Substance from the Culture Filtrate of Trichoderma. Phytopath. 26, 1068 (1936).
Johnson, J. R., F. W. Bruce, and J. D. Dutcher: Gliotoxin, the Antibiotic Principle of Gliocladium fimbriatin. J. Am. Chem. Soc. 65, 2005 (1943).
Crowfoot, D., and B. W. Rogers-Low: X-Ray Crystallography of Gliotoxin. Nature 153, 651 (1944).
Johnson, J. R., A. R. Kidwa, and J. S. Warner: Gliotoxin XI. A Related Antibiotic from Penicillium terlikowskii. Gliotoxin Monoacetate. J. Am. Chem. Soc. 75, 2110 (1953).
Richtsel, W. A., H. G. Schneider, B. J. Sloan, P. R. Grof, F. A. Miller, Q. R. Bartz, J. Ehrlich, and G. J. Dixon: Antiviral Activity of Gliotoxin. Nature 204, 1333 (1964).
Taylor, A.: In Biochemistry of Some Foodborne Microbial Toxins, ed. R. I. Mateles and G. N. Wogan, p. 69. Cambridge, Massachusetts: The M. I. T. Press. 1967.
Bell, M. R., J. R. Johnson, B. S. Wildi, and R. B. Woodward: The Structure of Gliotoxin. J. Am. Chem. Soc. 80, 1001 (1958).
Beecham, A. F., J. Fridrichsons, and A. Mc. L. Mathieson: The Structure and Absolute Configuration of Gliotoxin and the Absolute Configuration of Sporidesmin. Tetrahedron Letters 1956, 3131.
Lowe, G., A. Taylor, and L. C. Vining: Sporidesmins. VI. Isolation and Structure of Dehydrogliotoxin, a Metabolite of Penicillium terlikowskii. J. Chem. Soc. (C) 1966, 1799.
Safe, S., and A. Taylor: Sporidesmins. XI. The Reaction of Triphenylphosphine with Epipolythiodioxopiperazines. J. Chem. Soc. (C) 1971, 1189.
Fridrichsons, J., and A. Mc. L. Mathieson: The Structure of the Methylene Dibromide Adduct of Sporidesmin at — 150°. Acta Cryst. 18, 1043 (1965).
Weber, H. P.: Molecular Structure and Absolute Configuration of Chaetocin. Acta Cryst. B28, 2945 (1972).
Davis, B. R., and I. Bernal: The Crystal Structure of 2,5-Piperazinediones Having Epipolysulphide Bridges Between C3 and C6: The Structure of N,N’Dimethyl-3,6-epitetrathio-2,5-piperazinedione. Proc. Nat. Acad. Sci. 70, 279 (1973).
Leonard, N. J., T. W. Milligan, and T. L. Brown: Transannular Interactions between Sulphide and Ketone Groups. J. Am. Chem. Soc. 82, 4075 (1960).
Trown, P. W.: Antiviral Activity of N,N’-Dimethyl-3,6-epidithio piperazine-2,5dione. A Synthetic Compound Related to the Gliotoxins, LLS 88 α and β-Chetomin, and the Sporidesmins. Biochem. Biophys. Res. Commun. 33, 402 (1968).
Murdock, K. C., and R. B. Angier: Acetylaranotin: Displacement Reactions at the Disulphide Linkage. Chem. Commun. 1970, 55.
Schoberl, A., and E. Ludwig: Die Aufspaltung der Disulfidbindung mit Natriumsulfit und Kaliumcyanid und über die Colorimetrische Bestimmung von Sulfhydrylverbindungen und Disulfiden. Ber. 70B, 1422 (1937).
Beecham, A. F., and A. Mc. L. Mathieson: The Circular Dichroism of Gliotoxin. Tetrahedron Letters 1966, 3139.
Ziffer, H., U. Weiss, and E. Charney: Optical Activity of Non-planar Conjugated Dienes. IV. Interacting Chromophores in Gliotoxin. Tetrahedron 23, 3881 (1967).
Moscowitz, A., E. Charney, U. Weiss, and H. Ziffer: Optical Activity in Skewed Dienes. J. Am. Chem. Soc. 83, 4661 (1961).
Ali, M. S., J. S. Shannon, and A. Taylor: Isolation and Structures of 1,2,3,4Tetrahydro-1,4-dioxopyrazino[1,2-a]indoles from Cultures of Penicillium terlikowskii. J. Chem. Soc. 1968, 2044.
Nagarajan, N., L. L. Huckstep, D. H. Lively, D. L. Delong, M. M. Marsh, and N. Neuss: Aranotin and Related Metabolites from Arachniotus aureus. I. Determination of Structure. J. Am. Chem. Soc. 90, 2980 (1968).
Cosulich, D. B., N. R. Nelson, and J. H. Van Den Hende: Crystal and Molecular Structure of LLS 88 a, an Antiviral Epidithiapiperazinedione Derivative from Aspergillus terreus. J. Am. Chem. Soc. 90, 6519 (1968).
Moncrief, J. W.: Molecular Structure of Bisdethiodi(thiomethyl)acetylaranotin including Absolute Configuration. J. Am. Chem. Soc. 90, 6516 (1968).
Nagarajan, N., N. Neuss, and M. M. Marsh: Aranotin and Related Metabolites. III. Configuration and Conformation of Acetylaranotin. J. Am. Chem. Soc. 90, 6518 (1968).
Suhadolnik, R. J, and R. E. Chenoweth: Biosynthesis of Gliotoxin. I. Incorporation of Phenylalanine-l-and 2-C14. J. Am. Chem. Soc. 80, 4391 (1958).
Winstead, J. A., and R. J. Suhadolnik: Biosynthesis of Gliotoxin. II. Further Studies on the Incorporation of Carbon-14 and Tritium Labelled Precursors. J. Am. Chem. Soc. 82, 1644 (1960).
Johns, N., and G. W. Kirby: The Biosynthesis of Gliotoxin. Possible Involvement of a Phenylalanine Epoxide. Chem. Commun. 1971, 163.
Bu’Lock, J. D., and A. P. Ryles: The Biosynthesis of the Fungal Toxin, Gliotoxin. Chem. Commun. 1970, 1404.
Brannon, D. R., J. A. Mage, B. B. Molloy, and W. A. Day: Biosynthesis of Dithiadiketopiperazine Antibiotics. Comparison of Possible Aromatic Amino Acid Precursors. Biochem. Biophys. Res. Commun. 43, 588 (1971).
Bose, A. K., K. G. Das, P. T. Funke, I. Kugajersky, O. P. Shukla, K. S. Khandanchani, and R. J. Suhadolnik: Biosynthetic Studies on Gliotoxin Using Stable Isotopes and Mass Spectral Methods. J. Am. Chem. Soc. 90, 1038 (1968).
Jerina, D. M., J. W. Daly, B. Witkop, P. Zalzman-Nirenberg, and S. Udenfriend: The Role of Areneoxide-Oxepin Systems in the Metabolism of Aromatic Substrates. III. Formation of 1,2-Naphthalene Oxide from Naphthalene by Liver Microsomes. J. Am. Chem. Soc. 90, 6525 (1968).
Miller, P. A., P. W. Trown, W. Fulmar, G. O. Morton, and J. Karliner: An Epidithiapiperazinedione Antiviral Agent from Aspergillus terreus. Biochem. Biophys. Chem. Commun. 33, 219 (1968).
Machin, P. J., and P. G. Sammes: Addition of Sulphur Nucleophiles Across Dehydrocyclodipeptides. J. C. S. Perkin 1 1974, 698.
Pojer, P. M., and I. D. Rae: Synthesis of 2-Benzamido-2-mercaptopropionic Acid. Tetrahedron Letters 1971, 3077.
Steglich, W., H. Tanner, and R. Hurnaus: 2-Dichlormethylenpseudooxazolon-(5). Chem. Ber. 100, 1824 (1967).
Kaneda, A., and R. Sudo: The Preparation of α-Amino-α-benzylmercaptopropionic Acid Derivatives. Bull. Chem. Soc. (Japan) 43, 2159 (1970).
Patel, S. M., J. O. Currie, and R. K. Olsen: The Synthesis of N-Acyl-α-mercaptoalanine Derivatives. J. Org. Chem. 38, 126 (1973).
Wohl, A., and C. Oesterlin: Überführung der Weinsäure in Oxalessigsäure durch Wasserspaltung bei niederer Temperatur. Ber. 34, 1139 (1901).
Yoshimura, J., and Y. Sugiyama: An Attempted Synthesis of 3,6-Epidithio-2,5piperazinediones by Cyclization of N,N’-dialkyl-2,2’-dithiocinnamamides. Bull. Chem. Soc. (Japan) 45, 1554 (1972).
Ottenheym, H. C. J., T. F. Spande, and B. Witkop: Approaches to Analogs of Anhydrogliotoxin. J. Am. Chem. Soc. 95, 1989 (1973).
Poisel, H.. and U. Schmidt: Über die elektrophile Einführung von Alkylgruppen und Schwefelfunktionen in den 2,5-Dioxopiperazin-Kern. Chem. Ber. 105, 625 (1972).
Ohler, E., H. Poisel, F. Tataruch, and U. Schmidt: Synthese des Epidithio-Lprolyl-L-prolin Anhydrids. Chem. Ber. 105, 635 (1972).
Hind, T., and T. Sako: Synthesis of 3,6-Diethoxycarbonyl-3,6-epipolythio-2,5piperazinediones. Tetrahedron Letters 1971, 3127.
Ohler, E., F. Tataruch, and U. Schmidt: Über die Einführung von Säurestoffunktionen in Prolyl-prolinanhydrid mit Bleitetraacetat: Ein neuer Weg zum Epidisulfid des Prolyl-prolin-anhydrid. Chem. Ber. 106, 396 (1973).
Ohler, E., F. Tataruch, and U. Schmidt: Nucleophile Einführung von Schwefelfunktionen über Sulfon und Hydroxyderivate Cyclisches Dipeptide (Dioxopiperazine). Chem. Ber. 106, 165 (1973).
Kishi, Y., T. Fukuyama, and S. Nakatsuka: A New Method for the Synthesis of Epidithiodiketopiperazines. J. Am. Chem. Soc. 95, 6490 (1973).
Kishi, Y., T. Fukuyama, and S. Nakatsuka: A Total Synthesis of Dehydrogliotoxin. J. Am. Chem. Soc. 95, 6492 (1973).
Kishi, Y., S. Nakatsuka, T. Fukuyama, and M. Havel: A Total Synthesis of Sporidesmin A. J. Am. Chem. Soc. 95, 6493 (1973).
Ronaldson, J. W., A. Taylor, E. P. White, and R. J. Abraham: Sporidesmins. Part I. Isolation and Characterisation of Sporidesmin and Sporidesmin B. J. Chem. Soc. 1963, 3172.
Hodges, R., J. W. Ronaldson, A. Taylor, and E. P. White: Sporidesmin and Sporidesmin B. Chem. & Ind. (London) 1963, 42.
Jamieson, W. D., R. Rahman, and A. Taylor: Sporidesmins. Part VIII. Isolation and Structure of Sporidesmin D and Sporidesmin F. J. Chem. Soc. (C) 1969, 1564.
Przybylska, M., E. M. Gopalkrishna, A. Taylor, and S. Safe: X-ray Crystallographic Determination of the Stereochemistry of the Tetrathio-bridge in Sporidesmin G. J. C. S. Chem. Commun. 1973, 554.
Francis, E., R. Rahman, S. Safe, and A. Taylor: Sporidesmins. Part XII. Isolation and Structure of Sporidesmin G, a Naturally Occurring 3,6-Epitetrathiopiperazine2,5-dione. J. C. S. Perkin I 1972, 470.
Safe, S., and A. Taylor: Sporidesmins. Part X. Synthesis of Polysulphides by Reaction of Dihydrogen Disulphide with Disulphides and Thiols. J. Chem. Soc. (C) 1970, 432.
Rahman, R., S. Safe, and A. Taylor: The Stereochemistry of Polysulphides. Quart. Rev. 24, 233 (1970).
Hodges, R., and J. S. Shannon: The Isolation and Structure of Sporidesmin C. Austral. J. Chem. 19, 1059 (1966).
Horn, M. J., D. B. Jones, and S. J. Ringel: Isolation of a New Sulphur-containing Amino Acid (Lanthionine) from Sodium Carbonate Treated Wool. J. Biol. Chem. 138, 141 (1941).
Nakagawa, M., T. Kaneko, and H. Yamaguchi: Photoinduced Oxidation of Tryptamine Derivatives. Formation of Pyrrolo[2,3-b]indole and Nb-(4-Cyanobutadienyl)tryptamine. J. C. S. Chem. Commun. 1972, 603.
Ohno, M., T. F. Spande, and B. Witkop: Cyclisation of Tryptophan and Tryptamine Derivatives to 2,3-Dihydropyrrolo[2,3-b]indoles. J. Am. Chem. Soc. 92, 343 (1970).
Foote, C. S., S. Mazur, P. A. Burns, and D. Lerdal: Chemistry of Singlet Oxygen. XVII. 1,4-Addition Products from Styrene Derivatives. J. Am. Chem. Soc. 95, 586 (1973).
Amit, R. G., F. W. Eastwood, and I. D. Rae: Addition of a Highly Oxygenated Side Chain to an Indole Derivative. Chem. Commun. 1971, 1614.
Minato, H., M. Matsumoto, and T. Katayama: Verticillin A, a New Antibiotic from Verticillium sp. Chem. Commun. 1971, 44.
Minato, H., M. Matsumoto, and T. Katayama: Studies on the Metabolites of Verticillium sp. Structures of Verticillin A, B, and C. J. C. S. Perkin I 1973, 1819.
Hauser, D., H. P. Weber, and H. P. Sigg: Isolierung und Strukturaufklärung von Chaetocin. Helv. chim. Acta 53, 1061 (1970).
Hauser, D., H. R. Loosli, and P. Niklaus: Isolierung von 11 α,11 α’-Dihydroxychaetoxin am Verticillium tenerum. Helv. chim. Acta 55, 2182 (1972).
Waksman, S. A., and E. Bugie: Chaetomin, a New Antibiotic Substance produced by Chaetomium cochliodes. J. Bacteriol. 48, 527 (1944).
Safe, S., and A. Taylor: The Characterisation of Chetomin, a Toxic Metabolite of Chaetomium cochliodes and Chaetomium globosum. J. C. S. Perkin I 1972, 472.
Kato, A., T. Saeki, S. Suzuki, K. Ando, G. Tamura, and K. Arima: Oryzachloride, a New Antiviral Disulphide Dioxopiperazine Derivative. J. Antibiot. (Tokyo) 22, 322 (1969).
Argoudelis, A. D.: Melinacidins II, III, and IV. New 3,6-Epidithiadiketopiperazine Antibiotics. J. Antibiot. (Tokyo) 25, 171 (1972).
Kamiya, T., S. Maeno, M. Hashimoto, and Y. Mini: Bicyclomycin, a New Antibiotic. II. Structure Elucidation and Acyl Derivatives. J. Antibiot. (Tokyo) 25, 576 (1972).
Miyoshi, T., N. Miyawa, H. Aobi, M. Kohsaka, H. Sakai, and H. Imanaka: Bicyclomycin, a New Antibiotic. II. Taxonomy, Isolation, and Characterization. J. Antibiot. (Tokyo) 25, 569 (1972).
Nishida, M., Y. Mini, and T. Matsubara: Bicyclomycin, a New Antibiotic. III. In vitro and in vivo Antimicrobial Activity. J. Antibiot. (Tokyo) 25, 582 (1972).
Sharma, G. M., and P. R. Burkholder: Structure of Dibromophakellin, a New Bromine-containing Alkaloid from the Marine Sponge, Phakellia flabellata. Chem. Commun. 1971, 151.
Chen, Y.-S.: Studies on the Metabolic Products of Roselinia necatrix. I. Isolation and Characterization of Several Physiologically Active, Neutral Substances. Bull. Agric. Chem. Soc. Japan 24, 372 (1960).
Johnson, J. L., W. G. Jackson, and T. E. Eble: Isolation of L-leucyl-L-proline Anhydride from Microbiological Formulations. J. Am. Chem. Soc. 73, 2947 (1951).
Kodaira, Y.: Toxic Substances to Insects Produced by Aspergillus achraceus and Oospora destructor. Agr. Biol. Chem. (Tokyo) 25 261 (1961).
Birkenshaw, J. H., and Y. S. Mohammed: Studies in the Biosynthesis of Microorganisms. 111. The Production of L-Phenylalanine Anhydride (cis-L-3,6-dibenzyl2,5-dioxopiperazine) by Penicillium nigricans (Bainier) Thom. Biochem. J. 85, 523 (1962).
Brown, R., C. Kelly, and S. E. Wibberley: The Production of 3-Benzylidene-6isobutylidene-2,5-dioxopiperazine, 3,6-Dibenzylidene-2,5-dioxopiperazine, and 3,6Dibenzyl-2,5-dioxopiperazine by a Variant of Streptomyces noursei. J. Org. Chem. 30, 277 (1965).
Caesar, F., K. Janssen, and E. Mutschler: Nigragillin, a New Alkaloid from the Aspergillus niger Group. 1. Isolation and Structure Elucidation of Nigragillin and a Dioxopiperazine. Pharm. Acta Hely. 44, 676 (1969).
Jensen, N. P., C. O. Gitterman, T. Y. Chen, B. H. Arison, and J. L. Beck: Isolation of a New Antitumour Antibiotic from Streptomyces griseoluteus. Chem. and Eng. News April 14-th, 1973, p. 24.
Gerber, N. N.: Phenazines, Phenoxazinones, and Dioxopiperazines from Streptomyces thioluteus. J. Org. Chem. 32, 4055 (1967).
Heinemann, B., M. A. Kaplan, R. U. Muir, and I. R. Hooper: Amphomycin, a New Antibiotic. Antibiot. and Chemother. 3, 1239 (1953).
Casnati, G., A. Quilico, and A. Ricca: Aspergillus glaucus Group. XVIII. Echinulin. 12. Gazz. Chim. Ital. 92, 129 (1962).
Dutcher, J. D.: Aspergillic Acid, an Antibiotic Substance produced by Aspergillus flavus. III. The Structure of Hydroxyaspergillic Acid. J. Biol. Chem. 232, 785 (1958).
Yokotsuka, T., M. Sasaki, T. Kikuchi, Y. Asao, and A. Nobuhara: Compounds Produced by Moulds. I. Fluorescent Compounds Produced by Japanese Industrial Moulds. Bull. Agric. Chem. Soc. Japan 41, 32 (1967).
Yokotsuka, T., T. Kikuchi, M. Sasaki, and K. Oshita: Aflatoxin G — like Compounds with Green Fluorescence Produced by Japanese Industrial Moulds. Bull. Agric. Chem. Soc. Japan 42, 581 (1968).
Terao, M., K. Karasawa, N. Tanaka, H. Yonehara, and H. Umezawa: A New Antibiotic, Emimycin. J. Antibiot. Ser. A 13, 401 (1960).
Terao, M.: Emimycin, a New Antibiotic. II. The Structure of Emimycin. J. Antibiot. Ser. A 16, 182 (1963).
Yamazaki, M.: Deoxyneo- 3-hydroxyaspergillic Acid. Chem. Pharm. Bull. (Japan) 20, 2274 (1972).
Rahman, R., S. Safe, and A. Taylor: Sporidesmins. Part IX. Isolation and Structure of Sporidesmin E. J. Chem. Soc. (C) 1969, 1665.
Taylor, A.: The Toxicology of Sporidesmins and Other Epipolythiodioxopiperazines, in “Microbial Toxins”, ed. S. Kadis, A. Ciegler, and S. J. Ajl, Vol. VII, chapter 10. New York: Academic Press. 1971.
Cheeseman, G. W. H., and E. S. G. Werstuik: Recent Advances in Pyrazine Chemistry. Adv. Heterocyclic Chem. 14, 99 (1972).
Tamura, S., A. Susuki, Y. Aoka, and N. Otaki: Isolation of Several Dioxopiperazines from Peptone. Agr. Biol. Chem. (Japan) 28, 650 (1964)
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1975 Springer-Verlag/Wien
About this chapter
Cite this chapter
Sammes, P.G. (1975). Naturally Occurring 2,5-Dioxopiperazines and Related Compounds. In: Zechmeister, L., Herz, W., Grisebach, H., Kirby, G.W. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 32. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7083-0_2
Download citation
DOI: https://doi.org/10.1007/978-3-7091-7083-0_2
Publisher Name: Springer, Vienna
Print ISBN: 978-3-7091-7085-4
Online ISBN: 978-3-7091-7083-0
eBook Packages: Springer Book Archive