Fluorine containing amino acids : synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif
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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.
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
Organic & Biomolecular Chemistry
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
MA thanks the Egyptian Government for a Scholarship. DO’H thanks the Royal Society for a Royal Society Wolfson Research Merit Award.
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