L‐α‐Amino‐β‐thio‐ϵ‐caprolactam, a new sulfur‐containing Substrate for α‐amino‐ϵ‐caprolactam racemase

FEBS Letters

Ahmed, Syed Ashrafuddin¹  Esaki, Nobuyoshi¹  Tanaka, Hidehiko¹  Soda, Kenji¹ 

[1] Laboratory ofMicrobial Biochemistry, Institute for Chemical Research, Kyoto University, Uji, Kyoto-Fu 611, Japan

关键词: L-α-Amino-β-thio-ϵ-caprolactam;    S-(β-Aminoethyl)-L-cysteine-ϵ-lactam;    α-Amino-ϵ-caprolactam;    racemase;    Amine racemase;    Pyridoxal 5'-phosphate enzyme;   

DOI  :  10.1016/0014-5793(84)81081-9

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

A one-step synthesis of a new sulfur-containing compound, L-α-amino-β-thio-ϵ-caprolactam from L-cysteine methyl ester and 2-chloroethylamine has been described. This intramolecular cyclic amide of S-(β-aminoethyl)-L-cysteine serves as a good substrate for α-amino-ϵ-caprolactam racemase. L-α-Amino-β-thio-ϵ-caprolactam is racemized more than 3 times faster and binds about 4-fold stronger to the enzyme than L-α-amino-ϵ-caprolactam itself. Optimum pH for racemization of this new compound is about 10.0.

【 授权许可】

Unknown