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

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Abstract
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.