Synthesis of delta-(alpha-aminoadipyl)cysteinylvaline and its role in penicillin biosynthesis.
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.
D000164:Acremonium / Q000378:metabolism; D002474:Cell-Free System; D003545:Cysteine; D004151:Dipeptides / Q000138:chemical synthesis; D009842:Oligopeptides / Q000138:chemical synthesis*; D010406:Penicillins / Q000096:biosynthesis*; D010408:Penicillium chrysogenum / Q000378:metabolism; D011523:Protoplasts; D013237:Stereoisomerism; D014316:Tritium; D014633:Valine / Q000138:chemical synthesis
D004151:Dipeptides; D009842:Oligopeptides; D010406:Penicillins; D014316:Tritium; C011638:5-(2-aminoadipyl)cysteinylvaline; D014633:Valine; D003545:Cysteine