Abstract
Speculations regarding the biogenesis of natural products, particularly those of plant origin, have excited the interest of organic chemists for more than fifty years, and several basic ideas have persisted in spite of the technical impossibility of putting them to experimental test. The use of biochemical techniques involving labelled atoms, coupled with various other developments such as microchemistry and chromatography have now served to provide verification of some of these earlier ideas. The hypothesis that many complex natural products, including aromatic compounds, were built up from acetyl units was advanced by Collie in 19071) and, as a result of modern biochemical research is now known to be essentially correct. The well-known isoprene rule as a basis for terpenoid structure has also now been provided with solid biochemical backing. Similarly, the early ideas on amino-acids as precursors of alkaloids date back to a paper by Robinson in 19172). A more recent biogenetic hypothesis is based upon the growing realisation that free radical reactions play an important part in biochemical processes, and this has led to some novel biogenetic ideas which will be referred to. With the advent of the antibiotics, the range of available natural products has increased enormously both in number and type.
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References
J. N. Collie, J. Chem. Soc. 91, 1806 (1907).
R. Robinson, J. Chem. Soc. Ill, 876 (1917).
F. Lipmann, Proc. Nat. Acad. Sci. 44, 67 (1958); P. Berg and E. J. Offengand, ibid., p. 78.
B. D. Davis, Biosynthesis of the Aromatic Amino Acids, Chapter Via in: A Symposium on Amino Acid Metabolism, ed. by W. D. McElroy and H. B. Glass, ( The Johns Hopkins Press, Baltimore 1955 ).
P. Lynen, Nature 174, 962 (1954).
P. Lepmann, Science 120, 855 (1954).
J. V. Formica and R. O. Brady, J. Amer. Chem. Soc. 81 752 (1959).
S. J. Wakil, J. Amer. Chem. Soc. 80, 6465 (1958).
Various authors: Biosynthesis of Terpenes and Sterols, Ciba Foundation Symposium, London, ed. by G. E. W. Wolstenholme and M. O’connor (London 1959 ).
F. Lynen, H. Eggerer, U. Henning and I. Kessel, Angew. Chem. 70, 738 (1958).
J. W. Ogilvie jr. and R. G. Langdon, J. Amer. Chem. Soc. 81, 754 (1959); J. W. Ogilvie jr., ibid., p. 756.
D. H. R. Barton and T. Cohen, Some Biogenetic Aspects of Phenol Oxidation, in: Festschrift A. Stoll (Basel 1955 ), p. 117.
A. I. Scott, Proc. Chem. Soc. 1959, 195.
F. Bohlmann, Angew. Chem. 67, 389 (1955).
M. Anchel, Trans. N. Y. Acad. Sci. 16, 337 (1954).
J. D. Bu’lock and H. Gregory, Biochem. J. 72, 322 (1959).
J. Gripenberg, Acta Chem. Scand. 6, 580 (1952).
A. J. Birch and F. W. Donovan, Austr. J. Chem. 6, 360 (1953).
A. J. Birch, Biosynthetic Theories in Organic Chemistry, in: Perspectives in Organic Chemistry ( vol. ded. to Sir R. Robinson ), ed. by Sir A. R. Todd, Interscience Publishers, Inc., New York and London, (1956), p. 134.
A. J. Birch, R. A. Massy-Westropp and C. J. Moye, Chem. and Ind. 1955, 683.
A. J. Birch, R. A. Massy-Westropp, R. W. Rickards and H. Smith, J. Chem. Soc. 1958, 360.
A. J. Birch, P. Fitton, E. Pride, A. J. Ryan, H. Smith and W. B. Whalley, J. Chem. Soc. 1958, 4576.
J. MacMillan, J. Chem. Soc. 1954, 2585.
A. J. Birch, G. E. Blance and H. Smith, J. Chem. Soc. 1958, 4582.
F. W. Bassett and S. W. Tanenbaijm, Exper. 14, 38 (1958).
A. J. Birch and R. A. Massy-Westropp, J. Chem. Soc. 1957, 2215.
H. Brockmann and B. France:, Ber. dtseh. chem. Ges. 88, 1792 (1955).
R. B. Woodward, Angew. Chem. 69, 50 (1957); The Structure and Biogenesis of the Maerolides, a new Class of Natural Products, in: Festschrift A. Stoll (Basel 1957 ), p. 524.
P. P. Wiley, K. Gerzon, E. H. Flynn, M. V. Sigal jr., O. Weaver, U. C. Quarck, R. R. Chauvette and R. Monahan, J. Am. Chem. Soc. 79, 6062 (1957).
C. Djerassi and J. A. Zderic, J. Amer. Chem. Soc. 78, 6390 (1956).
C. Djerassi and O. Halpern, J. Amer. ehem. Soc. 79, 2022 (1957); Tetrahedron 3, 255 (1958).
H. Brockmann, Angew. Chem. 69, 237 (1957).
R. Anliker and K. Gubler, Helv. Chim. Acta 40, 119 (1957).
J. B. Patrick, R. B. Williams and J.S. Webb, J. Amer. chem. Soc. 80, 6689 (1958).
J. R. D. McCormick, N. O. Sjolander, U. Hirsch, E. R. Jensen and A. P. Doer- Schuk, J. Amer. chem. Soc. 79, 4561 (1957).
J. R. D. McCormick, PH. A. Miller, J. A. Growich, N. O. Sjolander and A. P. Doerschuk, J. Amer. chem. Soc. 80, 5572 (1958).
American Cyanamide Co. Austral. Patents 35376–7/57.
R. B. Woodward, Angew. Chem. 68, 13 (1956).
R. Robinson, The Structural Relations of Natural Products ( Clarendon Press, Oxford 1955 ).
A. J. Birch (private communication).
A. J. Birch, R. J. English, R. A. Massy-Westropp, M. Slaytor and H. Smith, J. Chem. Soc. 1958, 365; A. J. Birch, R. J. English, R. A. Massy-Westropp and H. Smith, ibid., p. 369.
R. K. Callow, Chem. Soc. Ann. Rep. 1956, 307; P. Bladon, ibid. 1957, 275.
H. S. Burton, E. P. Abraham and H. M. E. Cardwell, Bioehem. J. 62, 171 (1956).
N. J. Cartwright, Biochem. J. 60, 238 (1955).
S. A. Fusabi, R. P. Frohardt, A. Ryder, TH. H. Haskell, D. W. Johannessen, C. C. Elder and Q. R. Bartz, J. Am. Chem. Soc. 76, 2878 (1954); S. A. Fusabi, TH. H. Haskell, R. P. Frohardt and Q.R. Bartz, ibid. p. 2881.
L. Pons and H. Veldstra, Rec. Tray. Chim. 74, 1217 (1955).
H. W. Dion, S. A. Fusari, Z. L. Jakubowski, J. G. Zora and Q. R. Bartz, J. Amer. chem. Soc. 78, 3075 (1956).
F. A. Kuehl jr., F. J. Wolf, N. R. Tbenneb, R. L. Peck, E. Howe, B. D. Hunne- Well, G. Downing, E. Newstead, K. Folkers, R. P. Buhs, I. Putter, R. Ormond, J. E. Lyons and L. Chaiet, J. Amer. chem. Soc. 77, 2344 (1955).
G-. A. Snow, J. chem. Soc. 1954, 4080.
W. B. Sutton and L. Stanfield, Antibiotics and Chemotherapy 5, 582 (1955).
L. Ettlinger, E. Gaumann, R. Hutter, W. Keller-Schierlein, F. Kradolfer, L. Neipp, V. Prelog and H. Zahner, Helv. Chim. Acta 42, 563 (1959).
J. T. Edward, Ann. Rep. Chem. Soc. 51, 247 (1954).
D. W. Woolley, G. Schaitner and A. C. Brattn, J. Biol. Chem. 215, 485 (1955).
P. Fryth, C. W. Waller, B. L. Hutchings and J. H. Williams, J. Amer, chem. Soc. 80, 2736 (1958).
B. R. Baker, J. P. Joseph and J. H. Williams, J. Amer. ehem. Soc. 77, 1 (1955).
G. M. Tener, E. Van Tamelen and F. M. Strong, Fed. Proc. 12, 280 (1953).
P. Brookes, A. T. Fuller and J. Walker, J. Chem. Soc. 1957, 689.
H. E. V. Arnstein and P. T. Grant, Baet. Rev. 20, 133 (1956).
H. R. V. Arnstein, Ann. Rep. Chem. Soc. 54, 339 (1957).
F. R. Batchelor, F. P. Doyle, J. H. C. Nayler and G. N. Rolinson, Nature 183, 257 (1959).
E. P. Abraham, G. G. F. Newton and C. W. Hale, Bioehem. J. 58, 94 (1954).
G. G. P. Newton and E. P. Abraham, Nature 175, 548 (1955).
G. Dunn, J. J. Gallagher, G. T. Newbold and F. S. Spring, J. chem. Soc. 1959, SuppL 126; G. Dunn, G. T. Newbold and F. S. Spring, ibid., Suppl. 131.
A. J. Birch, R. A. Massy-Westropp and R. W. Rickards, Chem. and Ind. 1955, 1599.
M. R. Bell, J. R. Johnson, B. S. Wildi and R. B. Woodward, J. Amer. chem. Soc. 80, 1001 (1958).
PL. A. Plattner and U. Nager, Helv. Chim. Acta 31, 2192 (1948).
A. H. Cook, S. F. Cox and T. H. Farmer, Nature 162, 61 (1948).
PL. A. Plattner, N. Clattson-Kaas, A. Boller and U. Nager, Helv. Chim. Acta 31, 860 (1948).
TH. H. Haskell, S. A. Fitsari, R. P. Frohardt and Q. R. Bartz, J. Artier, chem. Soc. 74, 599 (1952).
H. E. Carter, R. K. Clark jr., P. Koim, J. W. Rothrock, W. R. Taylor, C. A. West, G. B. Whitfield and W. G. Jackson, J. Amer. chem. Soc. 76, 566 (1954).
K. Nakaniski, T. Ito and Y. Hirata, J. Amer. chem. Soc. 76, 2845 (1954).
D. E. Ames, R. E. Bowman, J. F. Cavalla and D. D. Evans, J. chem. Soc. 1955, 4260; D. E. Ames and R. E. Bowman, ibid., p. 4264.
W. A. Sexton, Chemical Constitution and Biobgical Activity, 2nd Edn. (Spon, London, 1953); German Edn.: Chemische Konstitution und biologische Wirkung, ( Verlag Chemie, Weinheim 1958 ), p. 193.
R. Schwyzer and P. Sieber, Helv. Chim. Acta 40, 624 (1957).
R. Schwyzer and P. Sieber, Helv. Chim. Acta 41, 1582 (1958).
E. Katchalski, A. Berger, L. Bichowsky-Slomnicki and J. Kurte, Nature 176, 118 (1955).
A. Paladini and L. C. Craig, J. Amer. ehem. Soc. 76, 688 (1954).
G. Biserte and M. Dautrevaux, Bull. Soc. Chim. Biol. 39, 795 (1957).
W. Hausmahn and L. C. Craig, J. Biol. Chem. 198, 405 (1952).
TH. Wieland and W. Schön, Lieb. Ann. Chem. 593, 157 (1955).
G. G. F. Newton and E. P. Abraham, Biochem. J. 53, 597 (1953).
I. M. Lockhabt, E. P. Abrahm and G. G. F. Newton, Biochem. J. 61, 534 (1955).
G. G. F. Newton, E. P. Abraham and N. K. Berridge, Nature 171, 606 (1953).
G. Alderton, J. Amer. ehem. Soc. 75, 2391 (1953).
A. Stracher and L. C. Craig, J. Amer. ehem. Soc. 81, 696 (1959).
H. Brockmann and H. Geeren, Lieb. Ann. Chem. 603, 216 (1957).
L. C. Vining and W. A. Taber, Canad. J. Chem. 35, 1109 (1957).
J. C. Sheehan, H. G. Zachau and W. B. Lawson, J. Amer. Chem. Soc. 80, 3349 (1958).
R. B. Arnold, A. W. Johnson and A. B. Mauger, J. chem. Soc. 1958, 4466.
W. Keller-Schierlein, M. LJ. Mihailovic and V. Prelog, Helv. Chim. Acta 42, 305 (1959).
H. Brockmann and H. Muxeeldt, Chem. Ber. 91, 1242 (1958).
A. Butenandt, Angew. Chem. 69, 16 (1957).
C. B. Thorne, C. G. Gomez and R. D. Housewright, J. Bact. 69, 357 (1955i); C. B. Thorne and D. M. Molnar, ibid. 70, 420 (1955n).
S. Blackburn, W. R. Middlebrook and H. Phillips, Nature 150, 57 (1942).
P. Desntjelle and A. Casal, Bioehim. Biophys. Acta 2, 64 (1948).
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Sexton, W.A. (1960). The Structure and Biogenesis of Certain Antibiotics. In: Jucker, E. (eds) Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des Recherches Pharmaceutiques, vol 2. Birkhäuser Basel. https://doi.org/10.1007/978-3-0348-7038-2_9
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