Minimising conformational bias in fluoroprolines through vicinal difluorination

Gert Jan Hofman; Emile Ottoy; Mark E. Light; Bruno Kieffer; Ilya Kuprov; Jose C. Martins; Davy Sinnaeve; Bruno Linclau

doi:10.1039/c8cc01493k

Minimising conformational bias in fluoroprolines through vicinal difluorination

Gert Jan Hofman
, Emile Ottoy
, Mark E. Light
, Bruno Kieffer
, Ilya Kuprov
, Jose C. Martins
, Davy Sinnaeve
, Bruno Linclau

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

Abstract

Monofluorination at the proline 4-position results in conformational effects, which is exploited for a range of applications. However, this conformational distortion is a hindrance when the natural proline conformation is important. Here we introduce (3S,4R)-3,4-difluoroproline, in which the individual fluorine atoms instil opposite conformational effects, as a suitable probe for fluorine NMR studies.

Original language	English GB
Pages (from-to)	5118-5121
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	40
DOIs	https://doi.org/10.1039/c8cc01493k
State	Published - 2018
Externally published	Yes

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c8cc01493k

Cite this

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title = "Minimising conformational bias in fluoroprolines through vicinal difluorination",

abstract = "Monofluorination at the proline 4-position results in conformational effects, which is exploited for a range of applications. However, this conformational distortion is a hindrance when the natural proline conformation is important. Here we introduce (3S,4R)-3,4-difluoroproline, in which the individual fluorine atoms instil opposite conformational effects, as a suitable probe for fluorine NMR studies.",

author = "Hofman, \{Gert Jan\} and Emile Ottoy and Light, \{Mark E.\} and Bruno Kieffer and Ilya Kuprov and Martins, \{Jose C.\} and Davy Sinnaeve and Bruno Linclau",

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8cc01493k",

language = "الإنجليزيّة",

volume = "54",

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number = "40",

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TY - JOUR

T1 - Minimising conformational bias in fluoroprolines through vicinal difluorination

AU - Hofman, Gert Jan

AU - Ottoy, Emile

AU - Light, Mark E.

AU - Kieffer, Bruno

AU - Kuprov, Ilya

AU - Martins, Jose C.

AU - Sinnaeve, Davy

AU - Linclau, Bruno

PY - 2018

Y1 - 2018

N2 - Monofluorination at the proline 4-position results in conformational effects, which is exploited for a range of applications. However, this conformational distortion is a hindrance when the natural proline conformation is important. Here we introduce (3S,4R)-3,4-difluoroproline, in which the individual fluorine atoms instil opposite conformational effects, as a suitable probe for fluorine NMR studies.

AB - Monofluorination at the proline 4-position results in conformational effects, which is exploited for a range of applications. However, this conformational distortion is a hindrance when the natural proline conformation is important. Here we introduce (3S,4R)-3,4-difluoroproline, in which the individual fluorine atoms instil opposite conformational effects, as a suitable probe for fluorine NMR studies.

UR - https://www.scopus.com/pages/publications/85047178548

U2 - 10.1039/c8cc01493k

DO - 10.1039/c8cc01493k

M3 - مقالة

C2 - 29717724

SN - 1359-7345

VL - 54

SP - 5118

EP - 5121

JO - Chemical Communications

JF - Chemical Communications

IS - 40

ER -

Minimising conformational bias in fluoroprolines through vicinal difluorination

Abstract

ASJC Scopus subject areas

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