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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
论文数: 0 引用数: 0
h-index: 0
机构:
NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA

Gao, Y
论文数: 0 引用数: 0
h-index: 0
机构:
NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA

Wang, XZ
论文数: 0 引用数: 0
h-index: 0
机构:
NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA

Kelley, JA
论文数: 0 引用数: 0
h-index: 0
机构:
NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA

Burke, TR
论文数: 0 引用数: 0
h-index: 0
机构:
NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA NCI, Med Chem Lab, Canc Res Ctr, NIH, Frederick, MD 21702 USA
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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