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PMID: 825110 Published · ppublish English Journal Article

Synthesis of delta-(alpha-aminoadipyl)cysteinylvaline and its role in penicillin biosynthesis.

The Biochemical journal ·Vol. 157 ·No. 3 ·1976-09-01 ·Pages 651-60

Fawcett PA, Usher JJ, Huddleston JA, Bleaney RC, Nisbet JJ, Abraham EP

Abstract

1. The stereoisomers of delta-(alpha-aminoadipyl)-L-cysteinylvaline (LLD, LLL and DLD) were synthesized from valine labelled with 3H in its methyl groups or in the alpha position. L-Cysteinyl-D-[4,4'-3H]valine was also synthesized. 2. 3H was incorporated into a compound that behaved like penicillin N when the LLD tripeptide containing either a methyl- or an alpha-labelled valine residue was incubated with a cell-free system prepared by lysis of protoplasts of Cephalosporium acremonium. 3. Incorporation was not observed under these conditions from the labelled all-L- or DLD-tripeptide, from L-cysteinyl-D-[4,4'-3H]valine, or of Penicillium chrysogenum appeared to be the LLD isomer, like that from C. acremonium. 5. These findings are discussed in relation to penicillin biosynthesis.

MeSH Terms
Acremonium/metabolism Cell-Free System Cysteine Dipeptides/chemical synthesis Oligopeptides/chemical synthesis Penicillins/biosynthesis Penicillium chrysogenum/metabolism Protoplasts Stereoisomerism Tritium Valine/chemical synthesis
Chemicals
Dipeptides Oligopeptides Penicillins Tritium 5-(2-aminoadipyl)cysteinylvaline Valine Cysteine
Authors & Affiliations
6 authors, click to expand affiliations / ORCID
Fawcett P A
Usher J J
Huddleston J A
Bleaney R C
Nisbet J J
Abraham E P
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21 references, click to expand
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Article Info
Journal
The Biochemical journal
Abbr.
Biochem J
ISSN
0264-6021
DOI
10.1042/bj1570651
Published
1976-09-01
Pages
651-60
Language
English
Region
England
NLM ID
2984726R
PMCID
PMC1163907
Subset
IM
External Links
PubMed source DOI: 10.1042/bj1570651 PMC Full Text View journal details
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