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

被引:26
作者
Ayoup, Mohammed Salah [1 ,2 ]
Cordes, David B. [1 ]
Slawin, Alexandra M. Z. [1 ]
O'Hagan, David [1 ]
机构
[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
[2] Univ Alexandria, Fac Sci, Dept Chem, Alexandria, Egypt
基金
英国工程与自然科学研究理事会;
关键词
EFFICIENT; ESTERS;
D O I
10.1039/c5ob00650c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:5621 / 5624
页数:4
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