Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine

被引：14

作者：

Erdbrink, Holger ^{[1
]}

Nyakatura, Elisabeth K. ^{[1
]}

Huhmann, Susanne ^{[1
]}

Gerling, Ulla I. M. ^{[1
]}

Lentz, Dieter ^{[1
]}

Koksch, Beate ^{[1
]}

Czekelius, Constantin ^{[1
]}

机构：

[1] Free Univ Berlin, Dept Chem & Biochem, D-14195 Berlin, Germany

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷

关键词：

amino acids; CD-spectroscopy; fluorine; helix propensity; organo-fluorine; trifluoroisoleucine; FLUORINATED AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; BETA-METHYLPHENYLALANINE; COILED-COILS; STABILITY; PEPTIDES; PROTEINS; PROPENSITIES; ISOMERS; CORE;

D O I：

10.3762/bjoc.9.236

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical route for the stereoselective synthesis of (2S,3S)-5,5,5-trifluoroisoleucine (L-5-F(3)Ile) and (2R,3S)-5,5,5-trifluoro-allo-isoleucine (D-5-F-3-allo-Ile) was developed. The hydrophobicity of L-5-F(3)Ile was examined and it was incorporated into a model peptide via solid phase peptide synthesis to determine its alpha-helix propensity. The alpha-helix propensity of 5-F(3)Ile is significantly lower than Ile, but surprisingly high when compared with 4'-F(3)Ile.

引用

页码：2009 / 2014

页数：6

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