By Abraham Goldin
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Extra info for Advances in Chemotherapy. Volume 2
A number of procedures have been described for the assay of cephalosporin C and its derivatives (Claridge and Johnson, 1962; Kavanagh, 1963; Alicino, 1961), and for the detection and estimation of these compounds after chromatography on paper (Newton and Abraham, 1956; Sneath and Collins, 1961; Thomas, 1961). Cephalosporin C has a molecular formula ( C i 6 H 2 i 0 8 N 3 S ) with two carbon and two oxygen atoms more than that of penicillin N. 61 μ, a position characteristic of that due to the stretching vibration of the C = 0 group in the fused ß-lactam ring in the penicillins.
IV. PENICILLIN Ν (CEPHALOSPORIN N) AND CEPHALOSPORIN C A. Isolation and Structure 1. Penicillin Ν Methods used for the production and isolation of penicillin Ν from Cephalosporium sp. CMI 49,137 and E. salmosynnematum have been summarized in an earlier review (Abraham, 1962). The purification of this substance presented special problems, since it had the lability of the common penicillins coupled with a zwitterion nature which rendered it insoluble in common organic solvents. A preparation was eventually obtained, however, which was sufficiently pure for use in structural investigations (Abraham and Newton, 1954), and subsequently an Nacetyl derivative of a nearly pure product was found to yield a crystal- The 33 Cephalosporins line Ν,Ν-dibenzylethylenediamine salt with the molecular formula C 3 2 H 43 0 7N 5S (Fusari and Machamer, 1957-1958).
However, no experimental evidence to support these claims was presented. A second possible pathway to cephalosporin C would be identical with that to penicillin Ν until after a tripeptide intermediate had been formed but would then diverge from the latter. According to a third hypothesis, the pathways followed by valine would diverge at an early stage. b. Effect of y-Hydroxyvaline. Irrespective of whether penicillin Ν was a precursor of cephalosporin C, it was clear that valine must become involved, at some stage or stages in the biosynthesis of cephalosporin C, in a more extensive oxidative process than that required for the biosynthesis of penicillin N.
Advances in Chemotherapy. Volume 2 by Abraham Goldin