Stereocontrolled synthesis of ψ[CH(CF3)NH]Gly-peptides

被引：67

作者：

Molteni, M

Volonterio, A

Zanda, M

机构：

[1] CNR, Ist Chim Riconoscimento Mol, Sez A Quilico, I-20131 Milan, Italy

[2] Politecn Milan, Dipartimento Chim Mat & Ingn Chim G Natta, I-20131 Milan, Italy

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol0354730

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel class of peptidomimetics having a stereogenic [CH(CF3)NH] replacement for a [CONH] peptide bond has been synthesized, The new compounds have been obtained in a stereocontrolled fashion using a kinetically controlled aza-Michael addition of chiral alpha-amino acid esters to trans-3,3,3-trifluoro-1-nitropropene. The stereoselectivity is strongly influenced by the solvent, the base, its stoichiometry, and the R side-chain. Diastereomeric ratios higher than 11:1 were achieved using H-Val-OtBu.HCl in toluene with 1.1 equiv of DIPEA.

引用

收藏

页码：3887 / 3890

页数：4

相关论文

共 19 条

[1]

Castelli VV, 2003, EUR J ORG CHEM, V2003, P627

[2] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[3] Partially modified retro-inverso peptides: Development, synthesis, and conformational behavior [J].

Fletcher, MD ;

Campbell, MM .

CHEMICAL REVIEWS, 1998, 98 (02) :763-795

[4]

GANTE J, 1994, ANGEW CHEM INT EDIT, V33, P1699, DOI 10.1002/anie.199416991

[5] Asymmetric carbon-carbon bond formations in conjugate additions of lithiated N-boc allylic and benzylic amines to nitroalkenes:: Enantioselective synthesis of substituted piperidines, pyrrolidines, and pyrimidinones [J].

Johnson, TA ;

Jang, DO ;

Slafer, BW ;

Curtis, MD ;

Beak, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11689-11698

[6] Organofluorine compounds and fluorinating agents .16. Monoalkylations and cycloadditions with trans-3,3,3-trifluoro-1-nitropropene [J].

Klenz, O ;

Evers, R ;

Miethchen, R ;

Michalik, M .

JOURNAL OF FLUORINE CHEMISTRY, 1997, 81 (02) :205-210

[7] Protease inhibitors: Current status and future prospects [J].

Leung, D ;

Abbenante, G ;

Fairlie, DP .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (03) :305-341

[8] Peptides as drugs: Is there a market? [J].

Loffet, A .

JOURNAL OF PEPTIDE SCIENCE, 2002, 8 (01) :1-7

[9] The Henry reaction: recent examples [J].

Luzzio, FA .

TETRAHEDRON, 2001, 57 (06) :915-945

[10]

McDaid P, 2002, ANGEW CHEM INT EDIT, V41, P338, DOI 10.1002/1521-3773(20020118)41:2<338::AID-ANIE338>3.0.CO