By Robert Morin
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Extra info for The Biology of Beta-Lactam Antibiotics. Volume 3: Biochemistry
Substitution of a formyl, a phenylacetyl, a phenoxyacetyl, glutaramido, 2(2-furyl)-2-methoxyiminoacetyl group, or hydrogen for the D-a-aminoadipyl group of 22 give compounds that do not serve as substrates of the enzyme. Unlike cell-free conversion of 18a to 22, the conversion of 22 to 23 is not stimulated by the presence of ATP. ATP, ADP, and GTP (1 or 10 mM) each inhibited the conversion of 22 to 23 (7-17% inhibition at a concentration of 1 mM and 92-97% inhibition at 10 mM) (Turner et al, 1978).
The acetyl- THE BIOSYNTHESIS OF ß-LACTAM ANTIBIOTICS 53 CoA : deacetylcephalosporin C O-acetyltransferase has been purified 104-fold from crude extracts of C. , 1976). Ether-treated C. acremonium cells, but not untreated cells, will take up 23; and in the presence of acetylCoA, the ether-treated cells convert 23 to 24 (Felix et al, 1980). S. Patent 3,926,729) apparently are deficient in acetylCoA : deacetylcephalosporin C O-acetyltransferase and produce 23 but little or no 24. S. , 1971). include: 18a —> 22 -» 23 -» 24, prior to methoxylation.
1975b). However, mutants that produce large amounts of the enzyme have been isolated. , No. , 1975b). B. Conversion of Deacetylcephalosporin C to OCarbamoyldeacetylcephalosporin C S. , 1971). Extracts of S. ^s> ^ ^ N . + 0 II H03P0-C-NH2 CH2OH C0 2 H (23) Deacetylcephalosporin C H2N H02C H \ I 0 II H H C-(CH2)3-C-N C H 2 0 - C - N H 2 + ΗΟΡΟ3Η C02H O-Carbamoyldeacetylcephalosporin C clavuligerus convert [3-hydroxymethyl-3Jï\de&cetylcephalosporm C and carbamoylphosphate into a radioactive compound with the same Chromatographie properties as 25.
The Biology of Beta-Lactam Antibiotics. Volume 3: Biochemistry by Robert Morin