Enantioselective synthesis of Nα-Fmoc protected (2S,3R)-3-phenylpipecolic acid.: A constrained phenylalanine analogue suitably protected for solid-phase peptide synthesis

被引:13
作者
Liu, DG [1 ]
Gao, Y [1 ]
Wang, XZ [1 ]
Kelley, JA [1 ]
Burke, TR [1 ]
机构
[1] NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA
关键词
D O I
10.1021/jo010124+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reported herein is the first enantioselective preparation of (2S,3R)-3-phenylpipecolic acid as a conformationally constrained phenylalanine analogue bearing N-a-protection suitable for solid-phase peptide synthesis. Stereochemistries at both the 2- and 3-positions are derived inductively from a single chiral center provided by the commercially available Evans chiral auxiliary, (4S)-4-benzyl-1,3-oxazolidin-2-one. By constraining phi and x(1) torsion angles, this novel amino acid analogue can serve as a useful tool for the induction of defined geometry in phenylalanine-containing peptides.
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页码:1448 / 1452
页数:5
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