The nonadrides are a small group of fungal metabolites characterised chemically by the presence of a nine-membered alicyclic ring and two five-ring anhydride functions. The first two members, glauconic and glaucanic acids, were isolated by Wijkman (18) in 1931 from a fungus described as Pé nicillium glaucum and in 1934 by Yuill (19) from a P. purpurogenum species. The third nonadride, byssochlamic acid, was obtained from Byssochlamys fulva by Raistrick and Smith (14) in 1933. Although extensive chemical work was carried out on glauconic acid by Wijkman, Kraft, Sutter and their co-workers (16, 17, 15, 12, 11) and on byssochlamic acid by Raistrick’s group (14) and by Cook, Loudon and Paton (7), the structures of the metabolites were not elucidated until the early sixties when these problems were solved chemically by Barton, Sutherland and their collaborators (1) and X-ray crystallographically by Robertson and Sim and their group (8, 9).
KeywordsMaleic Anhydride Absolute Configuration Labelling Pattern Succinic Anhydride Glutaric Acid
Unable to display preview. Download preview PDF.
- 2.Baldwin, J. E., D. H. R. Barton and J. K. Sutherland: The Nonadrides. IV. The Constitution and Stereochemistry of Byssochlamic Acid. J. Chem. Soc. (London) 1965, 1787.Google Scholar
- 3.Barton, D. H. R., L. D. S. Godinho and J. K. Sutherland: The Nonadrides. III. The Absolute Configuration of Glauconic and Glaucanic Acids. J. Chem. Soc. (London) 1965, 1779.Google Scholar
- 4.Barton, D. H. R., L. M. Jackman, L. Rodriguez-Hahn and J. K. Sutherland: The Nonadrides. II. The Constitutions of Glauconic and Glaucanic Acids. J. Chem. Soc. (London) 1965, 1772.Google Scholar
- 5.Barton, D. H. R. and J. K. Sutherland: The Nonadrides. I. Introduction and General Survey. J. Chem. Soc. (London) 1965, 1769.Google Scholar
- 6.Bloomer, J. L., C. E. Moppett and J. K. Sutherland: The Biosynthesis of Glauconic Acid. Chem. Commun. 1965, 619.Google Scholar
- 7.Cook, J. W., J. D. Loudon and R. P. Paton; see R. P. Paton: Thesis, Univ. Glasgow. 1954.Google Scholar
- 8.Ferguson, G., J. M. Robertson and G. A. Sim: The Stereochemistry of Glauconic Acid. Proc. Chem. Soc. (London) 1962, 385.Google Scholar
- 9.Hamor, T. A., I. C. Paul, J. M. Robertson and G. A. Sim: Fungal Metabolites. II. The Structure of Byssochlamic Acid: X-Ray Analysis of Byssochlamic Acid Bis-p-bromophenyl Hydrazide. J. Chem. Soc. (London) 1963, 5502.Google Scholar
- 12.Kraft, K. und H. Porsch: Zur Konstitution der Glaukonsäuren. V. Untersuchungen am Glaukonin. Liebigs Ann. Chem. 527, 168 (1936).Google Scholar
- 13.Moppett, C. E. and J. K. Sutherland: unpublished.Google Scholar
- 14.Raistrick, H. and G. Smith: Studies in the Biochemistry of Micro-organisms. XXXV. The Metabolic Products of Byssochlamys fulva Olliver and Smith. Biochem. J. 27, 1814 (1933); and unpublished observations.Google Scholar
- 17.Zur Konstitution der Glaukonsäuren. III. Liebigs Ann. Chem. 519, 97 (1935)Google Scholar
- 19.Yuill, J. L.: The Acids Produced from Sugar by a Pé nicillium Parasitic upon Aspergillus niger. Biochem. J. 28, 222 (1934).Google Scholar