Asymmetric synthesis ofS-alkyl-substituted (R)-cysteinesvia a chiral NiII complex of the Schiff's base of dehydroalanine with (S)-2-N-(N-benzylprolyl)aminobenzophenone |
| |
Authors: | A S Saghiyan A V Geolchanyan S M Djamgaryan S M Vardapetyan V I Tararov N A Kuz'mina N S Ikonnikov Yu N Belokon M North |
| |
Institution: | (1) Institute of Biotechnology of the Ministry of Industry of the Republic of Armenia, 14 ul. Gyurdzhyana, 375056 Erevan, Republic of Armenia;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813 Moscow, Russian Federation;(3) Department of Chemistry, London Kings College, Strand, WC2R 2LS London, UK |
| |
Abstract: | An efficient procedure was developed for the asymmetric synthesis ofS-alkyl derivatives of (R)-cysteine by nucleophilic addition of alkanethiols (BunSH, ButSH, ortert-C5H11SH) to the C=C bond of the dehydroalanine fragment in the NiII complex of the Schiff's base of Δ-Ala with (S)-2-N-(N-benzylprolyl)aminobenzophenone (S)-BPB-Δ-Ala]NiII. Under conditions of thermodynamic control of the reaction, the diastereomeric excess of the complexes with the (S.R)-configuration was 88–96%. After decomposition of the complexes,(R)-S-butylcysteine,(R)-S-tert-butylcysteine, and(R)-S-tert-pentylcysteine were isolated with an enantiomeric purity of >97%.
Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1467–1470, August, 2000. |
| |
Keywords: | dehydroalanine thiols addition diastereoselectivity S-alkylcysteines asymmetric synthesis |
本文献已被 SpringerLink 等数据库收录! |
|