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

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

A practical route for the stereoselective synthesis of (2S,3S)-5,5,5-trifluoroisoleucine (L-5-F3Ile) and (2R,3S)-5,5,5-trifluoro-allo-isoleucine (D-5-F3-allo-Ile) was developed. The hydrophobicity of L-5-F3Ile was examined and it was incorporated into a model peptide via solid phase peptide synthesi...

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Bibliographic Details
Main Authors: Holger Erdbrink, Elisabeth K. Nyakatura, Susanne Huhmann, Ulla I. M. Gerling, Dieter Lentz, Beate Koksch, Constantin Czekelius
Format: Article
Language:English
Published: Beilstein-Institut 2013-10-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
amino acids
CD-spectroscopy
fluorine
helix propensity
organo-fluorine
trifluoroisoleucine
Online Access:https://doi.org/10.3762/bjoc.9.236

Internet

https://doi.org/10.3762/bjoc.9.236

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