期刊
TETRAHEDRON
卷 56, 期 12, 页码 1715-1723出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(00)00075-2
关键词
beta-homo-peptides; beta(2,2)-HBip; alpha,alpha-disubstituted beta-amino acids
A novel beta(2,2)-gem-disubstituted amino acid, beta(2,2)-HBip, has been synthesized by alpha,alpha-bis-alkylation of alkyl cyanoacetates with 2,2'-bis-(bromomethyl)-1,1'-diphenyl, followed by NaBH4/CoCl2 reduction of the cyano group. Both its C- and N-protected derivatives have been obtained. A slow interconversion at the NMR time scale is generally observed between the two enantiomers of the conformationally labile beta(2,2)-HBip residue. The homo-peptides Boc-(beta(2,2)-HBip)(n)-OMe have been prepared in solution by the EDC/HOBt coupling method to the hexamer level and a preliminary conformational analysis has been performed by H-1 NMR and FT-IR absorption techniques. (C) 2000 Elsevier Science Ltd. All rights reserved.
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