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Paper | Special issue | Vol 52, No. 1, 2000, pp.425-442
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S52
Synthesis of N,N'-Unsymmetrical Diacylcystines and Cystine-containing Dipeptides

Eiji Kawanishi, Kyoichi Higuchi, and Akihiko Ishida*

*Medicinal Chemistry Research Laboratory, Tanabe Seiyaku Co.Ltd., 2-2-50, Kawagishi, Toda, Saitama 335-8505, Japan


N,N'-Unsymmetrical diacylcystines ((RR)-1 and (SS)-1) were prepared in good yields by three-step reaction sequences starting from cystine diethyl esters ((RR)-5 and (SS)-5). The key step reaction for diacylcystine synthesis, cleavage of diacylcystine diethyl esters ((RR)-2 and (SS)-2) proceeded with no detectable racemization of the products ((RR)-1 and (SS)-1). Cystine-containing dipeptides ((RRS)-3, (RRR)-3, and (SSR)-3) were also prepared in high yields and in high optical purity.