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

Holger Erdbrink; Elisabeth K. Nyakatura; Susanne Huhmann; Ulla I.M. Gerling; Dieter Lentz; Beate Koksch; Constantin Czekelius

doi:10.3762/bjoc.9.236

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

Holger Erdbrink, Elisabeth K. Nyakatura, Susanne Huhmann, Ulla I.M. Gerling, Dieter Lentz, Beate Koksch, Constantin Czekelius

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

A practical route for the stereoselective synthesis of (2S,3S)-5,5,5- trifluoroisoleucine (L-5-F3Ile) and (2R,3S)-5,5,5-trifluoro-alloisoleucine (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.

Original language	English (US)
Pages (from-to)	2009-2014
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	9
DOIs	https://doi.org/10.3762/bjoc.9.236
State	Published - Oct 2 2013
Externally published	Yes

Keywords

Amino acids
CD-spectroscopy
Fluorine
Helix propensity
Organo-fluorine
Trifluoroisoleucine

ASJC Scopus subject areas

Organic Chemistry

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10.3762/bjoc.9.236

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@article{141419feac8745a9831bdb0b9f299c7e,

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

abstract = "A practical route for the stereoselective synthesis of (2S,3S)-5,5,5- trifluoroisoleucine (L-5-F3Ile) and (2R,3S)-5,5,5-trifluoro-alloisoleucine (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.",

keywords = "Amino acids, CD-spectroscopy, Fluorine, Helix propensity, Organo-fluorine, Trifluoroisoleucine",

author = "Holger Erdbrink and Nyakatura, {Elisabeth K.} and Susanne Huhmann and Gerling, {Ulla I.M.} and Dieter Lentz and Beate Koksch and Constantin Czekelius",

year = "2013",

month = oct,

day = "2",

doi = "10.3762/bjoc.9.236",

language = "English (US)",

volume = "9",

pages = "2009--2014",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

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TY - JOUR

T1 - Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine

AU - Erdbrink, Holger

AU - Nyakatura, Elisabeth K.

AU - Huhmann, Susanne

AU - Gerling, Ulla I.M.

AU - Lentz, Dieter

AU - Koksch, Beate

AU - Czekelius, Constantin

PY - 2013/10/2

Y1 - 2013/10/2

N2 - A practical route for the stereoselective synthesis of (2S,3S)-5,5,5- trifluoroisoleucine (L-5-F3Ile) and (2R,3S)-5,5,5-trifluoro-alloisoleucine (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.

AB - A practical route for the stereoselective synthesis of (2S,3S)-5,5,5- trifluoroisoleucine (L-5-F3Ile) and (2R,3S)-5,5,5-trifluoro-alloisoleucine (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.

KW - Amino acids

KW - CD-spectroscopy

KW - Fluorine

KW - Helix propensity

KW - Organo-fluorine

KW - Trifluoroisoleucine

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U2 - 10.3762/bjoc.9.236

DO - 10.3762/bjoc.9.236

M3 - Article

C2 - 24204411

AN - SCOPUS:84885664622

SN - 1860-5397

VL - 9

SP - 2009

EP - 2014

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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