Synthesis of Stapled β3-Peptides through Ring-Closing Metathesis

被引：25

作者：

Bergman, Ylva E. ^{[1
]}

Del Borgo, Mark P. ^{[2
]}

Gopalan, Romila D. ^{[2
]}

Jalal, Sania ^{[1
]}

Unabia, Sharon E. ^{[2
]}

Ciampini, Marisa ^{[1
]}

Clayton, Daniel J. ^{[2
]}

Fletcher, Jordan M. ^{[2
]}

Mulder, Roger J. ^{[3
]}

Wilce, Jacqueline A. ^{[2
]}

Aguilar, Marie-Isabel ^{[2
]}

Perlmutter, Patrick ^{[1
]}

机构：

[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia

[2] Monash Univ, Dept Biochem & Mol Biol, Clayton, Vic 3800, Australia

[3] CSIRO Mol & Hlth Technol, Clayton, Vic 3169, Australia

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 19期

关键词：

BETA-PEPTIDES; 14-HELIX STABILITY; DESIGN; EFFICIENT; METHANOL;

D O I：

10.1021/ol901803d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of carbon-stapled beta(3)-peptides is reported. The precursor beta(3)-peptides, with -allyl beta-serines located in an i/i+3 relationship, were prepared on solid phase. We show that efficient ring-closing metathesis (RCM) of these new beta(3)-peptides proceeds smoothly either in solution or on an appropriate solid support. All products were generated with high selectivity for the E-isomer.

引用

页码：4438 / 4440

页数：3

共 34 条

[1] Inhibition of herpes simplex virus type 1 infection by cationic β-peptides [J].

Akkarawongsa, Radeekorn ;

Potocky, Terra B. ;

English, Emily P. ;

Gellman, Samuel H. ;

Brandt, Curtis R. .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2008, 52 (06) :2120-2129

[2] Design, machine synthesis, and NMR-solution structure of a β-heptapeptide forming a salt-bridge stabilised 314-helix in methanol and in water [J].

Arvidsson, PI ;

Rueping, M ;

Seebach, D .

CHEMICAL COMMUNICATIONS, 2001, (07) :649-650

[3] Sophistication of foldamer form and function in vitro and in vivo [J].

Bautista, Arjel D. ;

Craig, Cody J. ;

Harker, Elizabeth A. ;

Schepartz, Alanna .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2007, 11 (06) :685-692

[4] The synthesis of Fmoc-O-allyl β-serine [J].

Bergman, Ylva ;

Ciampini, Marisa ;

Jalal, Sania ;

Lagiakos, Helen Rachel ;

Aguilar, Marie-Isabel ;

Perlmutter, Patrick .

TETRAHEDRON-ASYMMETRY, 2008, 19 (24) :2861-2863

[5]

Blackwell HE, 1998, ANGEW CHEM INT EDIT, V37, P3281, DOI 10.1002/(SICI)1521-3773(19981217)37:23<3281::AID-ANIE3281>3.0.CO

[6]

2-V

[7] Facile and E-selective intramolecular ring-closing metathesis reactions in 310-helical peptides:: A 3D structural study [J].

Boal, Amie K. ;

Guryanov, Ivan ;

Moretto, Alessandro ;

Crisma, Marco ;

Lanni, Erica L. ;

Toniolo, Claudio ;

Grubbs, Robert H. ;

O'Leary, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (22) :6986-+

[8] Metathesis in peptides and peptidomimetics [J].

Brik, Ashraf .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (11-12) :1661-1675

[9] An efficient strategy for the preparation of one-bead-one-peptide libraries on a new biocompatible solid support [J].

Camperi, SA ;

Marani, MM ;

Iannucci, NB ;

Côté, S ;

Albericio, F ;

Cascone, O .

TETRAHEDRON LETTERS, 2005, 46 (09) :1561-1564

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

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

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

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