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Fluorine containing amino acids : synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif

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Hagan_2015_OBC_Fluorine_AM.pdf (209.7Kb)
Date
28/05/2015
Author
Ayoup, Mohammed Salah
Cordes, David Bradford
Slawin, Alexandra Martha Zoya
O'Hagan, David
Keywords
QD Chemistry
DAS
Metadata
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Abstract
A synthesis of two (S)-phenylalanine derivatives is described which have the all-cis, 2,3,5,6-tetrafluorocyclohexyl motif attached to the aromatic ring at the meta and para positions; the para substituted isomer is elaborated into illustrative dipeptides via the free amine and carboxylate respectively demonstrating its utility as a novel amino acid for peptide synthesis and offering a vehicle for incorporation of this unique and facially polarized ring system into bioactive compounds.
Citation
Ayoup , M S , Cordes , D B , Slawin , A M Z & O'Hagan , D 2015 , ' Fluorine containing amino acids : synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif ' Organic & Biomolecular Chemistry , vol 13 , no. 20 , pp. 5621-5624 . DOI: 10.1039/C5OB00650C
Publication
Organic & Biomolecular Chemistry
Status
Peer reviewed
DOI
http://dx.doi.org/10.1039/C5OB00650C
ISSN
1477-0520
Type
Journal article
Rights
Copyright 2015 the Authors. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at http://dx.doi.org/10.1039/C5OB00650C
Description
MA thanks the Egyptian Government for a Scholarship. DO’H thanks the Royal Society for a Royal Society Wolfson Research Merit Award.
Collections
  • Biomedical Sciences Research Complex (BSRC) Research
  • Chemistry Research
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/8616

Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.

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