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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Veröffentlicht in:Beilstein journal of organic chemistry 2013-10, Vol.9 (1), p.2009-2014
Hauptverfasser: Erdbrink, Holger, Nyakatura, Elisabeth K, Huhmann, Susanne, Gerling, Ulla I M, Lentz, Dieter, Koksch, Beate, Czekelius, Constantin
Format: Artikel
Sprache:eng
Schlagworte:
amino acids
CD-spectroscopy
Chemistry
fluorine
Full Research Paper
helix propensity
organo-fluorine
trifluoroisoleucine
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Zusammenfassung: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 synthesis to determine its α-helix propensity. The α-helix propensity of 5-F3Ile is significantly lower than Ile, but surprisingly high when compared with 4'-F3Ile.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.9.236