Robert Robinson and penicillin: An unnoticed document in the saga of its structure

Journal of Peptide Science

Volumn 13, Issue 12, 2007, Pages 769-775

  Curtis, Rachel ^a   Jones, John ^a,b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b BALLIOL COLLEGE   (United Kingdom)

Author keywords

Penicillin, structure of; Robinson Robert

Indexed keywords

BARIUM SULFATE; BETA LACTAM ANTIBIOTIC; OXAZOLONE; PENICILLAMINE; PENICILLIN G; SULFUR; THIAZOLE DERIVATIVE; THIOURACIL;

ACYLATION; ARTICLE; CRYSTAL STRUCTURE; DRUG FORMULATION; DRUG STRUCTURE; HUMAN; ISOMERISM; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

CHEMISTRY, ORGANIC; GREAT BRITAIN; HISTORY, 20TH CENTURY; MOLECULAR STRUCTURE; PENICILLINS;

EID: 37349119329     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.888     Document Type: Article

References (34)

1. Curtis R, Jones J. Peptide chemistry at Oxford before the Second World War. J. Pept. Sci. 2006; 12: 563-568.
2. Clarke HT, Johnson JR, Robinson R (eds.). The Chemistry of Penicillin. Princeton: 1949; hereafter cited as CP.
3. Clarke HT, Johnson JR, Robinson R. Brief History of the Chemical Study of Penicillin, CP, 3-9.
4. Chain EB. The Chemical Structure of the Penicillins, Nobel Lecture, 20 March 1946.
5. Abraham EP. From penicillins to cephalosporins. In 50 Years of Penicillin Application, Kleinkauf H, von Dohren H (eds.). Berlin, 1991; 7-23, hereafter cited as Abraham op. cit.(a).
6. Abraham EP. Sir Robert Robinson and the early history of penicillin. Nat. Prod. Rep. 1987; 4: 41-46, Hereafter cited as Abraham op. cit.(b).
7. Abraham EP. Sir Ernst Boris chain. Biogr. Mem. Fellows Roy. Soc. 1983; 29: 43-91, See especially pp. 55-58, hereafter cited as Abraham op.cit.(c).
8. Ferry G. Dorothy Hodgkin, a Life, See especially Chapter 6, London, 1998; 180-230, hereafter cited as Ferry op. cit.
9. Sheehan JC. The Enchanted Ring; the Untold Story of Penicillin. Cambridge, Massachussetts, 1982; hereafter cited as Sheehan op. cit..
10. Robinson R. Chemistry of Penicillin. A draft chapter for a second volume of memoirs which were never published, n.d., ca. 1971. Robinson Papers, Royal Society Library: London, A37.
11. Hodgkin DC. Penicillin. Text of an unidentified lecture, n.d, but after 1986 on internal evidence. Dorothy Hodgkin Papers, Bodleian Library: Oxford, A14.
12. Robinson R. The early stages of the chemical study of penicillin. Ramsden Memorial Lecture 1950. Mem. Proc. Manch. Lit. Philos. Soc. 1950-1951; 92: 124-143.
13. See correspondence in EP Abraham Papers, Bodleian Library Oxford, H228-H230.
14. Abraham EP. Letter to Baker of 14 Sept 1971, EP Abraham Papers, Bodleian Library: Oxford, H228.
15. Cornforth JW. E-mail correspondence with the author, April-May 2006.
16. Curtis R. Oxford Organic Chemistry 1914-1945, Chemistry Part II thesis, Oxford, 2006; 25-30.
17. Baker W. Some Recollections of the Early Work on Penicillamine, Unpublished notes written for Robinson, 1971; EP Abraham Papers, Bodleian Library: Oxford, H229.
18. Abraham EP. Letter to Robinson of 4 August 1971, EP Abraham Papers, Bodleian Library Oxford, H228.
19. CP, p. 4; Abraham op. cit.(a), p. 12 and op. cit.(b) p 43.
20. Abraham, op. cit. (c).
21. Abraham EP, Baker W, Chain E, Robinson R. Further studies on the degradation of penicillin. VII. British Ministry of Supply Penicillin Production Committee Report No. PEN. 103. There are at least two copies, slightly differing, in the EP Abraham Papers, Bodleian Library Oxford, C153 and C161. Another copy is partly directly reproduced in Abraham op. cit. (a) with the date given therein as "22 October 1945". Also reproduced in Abraham op. cit. (a) is part of a copy of Medical Research Council Committee on Penicillin Synthesis Report No. CPS 554, by Abraham Baker and Chain only, of 1945, in which they record that they "believe it to be established that their original β-lactam formula represents the correct structure of penicillin..."; but the dating and crossreferencing is a tissue of confusion, as they refer to PEN. 103 as "Pen. Report 105" and describe it as of "October 1945". For one of the most significant organic structures ever investigated, it seems worth clarifying the dating of the first formally recorded correct (albeit hesitant) proposal: PEN. 103 is dated 22 October 1943 (received in the USA January 1944) in CP, p. 1043; official copy number 32 in EP Abraham Papers, Bodleian Library Oxford, C161 bears date 22 October 1943 under the main part of the report and 23 October 1943 under the Addendum. According to CP, pp. 63 and 1056, Merck & Co Inc. Report No. M.1 of November 1943 (received in England February 1944) stated that "the four-membered lactam fused upon a five-membered heterocyclic ring (the β-lactam structure XLVI) appears unlikely unless the strain could account for the reactivity to methanol and benzylamine".
22. CP, p 7.
23. Robinson R. The Interpretation of the Reactions of Penicillin and Remarks on the Constitution of Penicillin. CP, pp 449-454.
24. Sheehan op. cit. p 115.
25. Jansen ABA, Robinson R. The synthesis of methyl benzylpenillonate. Monatsh. Chem. 1967; 98: 1017-1926.
26. Dorothy Hodgkin, letter to Marjorie Senechal, 28 March 1977, copy in Dorothy Hodgkin Papers, Bodleian Library Oxford, H.256. Cited in Ferry op. cit., p 214.
27. CP, p 160.
28. CP, p 8.
29. CP, p 270.
30. CP, p 281.
31. Abraham op. cit. (a) and (b); National Portrait Gallery London, NPG, p 562.
32. CP, p 419.
33. Woodward RB. Theoretical Aspects of the Reactions of Penicillins. CP, 443-449.
34. Sheehan op. cit., p 105.