✦ LIBER ✦
Synthesis of a S-(Carboxymethyl)cysteine Analog of (L-2-Amino-6-adipyl)-L-cysteinyl-D-valine and its Cell Free Biosynthetic Conversion into 6-[2-(D-2-Amino-2-carboxyethyl)thio) acetamido]penicillanic Acid
✍ Scribed by James E. Shields; Charles S. Campbell; Dale C. Duckworth; Norbert Neuss; Steven W. Queener
- Publisher
- John Wiley and Sons
- Year
- 1984
- Tongue
- German
- Weight
- 342 KB
- Volume
- 67
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
A new tripeptide (dimer), bis[(L‐cysteine‐S‐acetyl)‐L‐hemicystinyl(S^2^ → S^2^)‐D‐valine] (6) was synthesized by coupling N‐(tert‐butoxycarbonyl)‐S‐carboxymethyl‐L‐cysteine benzyl ester (1) with S‐trityl‐L‐cysteinyl‐D‐valine benzyl ester and subsequent removal of the protecting groups. After reduction of the disulfide, the free tripeptide Cys (CH~2~CO‐Cys‐D‐Val) (Ib) was used as a substrate of isopenicillin‐N synthetase in a cell‐free conversion to 6‐[2‐((D‐2‐amino‐2‐carboxyethyl)thio)acetamido]penicillanic acid (IIa).