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-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 sy...

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Autores principales: Erdbrink, Holger, Nyakatura, Elisabeth K, Huhmann, Susanne, Gerling, Ulla I M, Lentz, Dieter, Koksch, Beate, Czekelius, Constantin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817528/
https://www.ncbi.nlm.nih.gov/pubmed/24204411
http://dx.doi.org/10.3762/bjoc.9.236
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author Erdbrink, Holger
Nyakatura, Elisabeth K
Huhmann, Susanne
Gerling, Ulla I M
Lentz, Dieter
Koksch, Beate
Czekelius, Constantin
author_facet Erdbrink, Holger
Nyakatura, Elisabeth K
Huhmann, Susanne
Gerling, Ulla I M
Lentz, Dieter
Koksch, Beate
Czekelius, Constantin
author_sort Erdbrink, Holger
collection PubMed
description 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 α-helix propensity. The α-helix propensity of 5-F(3)Ile is significantly lower than Ile, but surprisingly high when compared with 4’-F(3)Ile.
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spelling pubmed-38175282013-11-07 Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine Erdbrink, Holger Nyakatura, Elisabeth K Huhmann, Susanne Gerling, Ulla I M Lentz, Dieter Koksch, Beate Czekelius, Constantin Beilstein J Org Chem Full Research Paper 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 α-helix propensity. The α-helix propensity of 5-F(3)Ile is significantly lower than Ile, but surprisingly high when compared with 4’-F(3)Ile. Beilstein-Institut 2013-10-02 /pmc/articles/PMC3817528/ /pubmed/24204411 http://dx.doi.org/10.3762/bjoc.9.236 Text en Copyright © 2013, Erdbrink et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Erdbrink, Holger
Nyakatura, Elisabeth K
Huhmann, Susanne
Gerling, Ulla I M
Lentz, Dieter
Koksch, Beate
Czekelius, Constantin
Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine
title Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine
title_full Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine
title_fullStr Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine
title_full_unstemmed Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine
title_short Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine
title_sort synthesis of enantiomerically pure (2s,3s)-5,5,5-trifluoroisoleucine and (2r,3s)-5,5,5-trifluoro-allo-isoleucine
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817528/
https://www.ncbi.nlm.nih.gov/pubmed/24204411
http://dx.doi.org/10.3762/bjoc.9.236
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