Microreactor synthesis of β-peptides

被引：91

作者：

Floegel, Oliver ^{[1
]}

Codee, Jeroen D. C. ^{[1
]}

Seebach, Dieter ^{[1
]}

Seeberger, Peter H. ^{[1
]}

机构：

[1] ETH, Swiss Fed Inst Technol, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 42期

关键词：

beta-peptides; fluorous tags; microreactors; synthetic methods;

D O I：

10.1002/anie.200602167

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Taming the insoluble: The reaction parameters of a β-peptide synthesis were optimized using only small amounts of reagents in a silicon microreactor (see picture). The use of unusually high temperatures (up to 120°C) reduces the reaction times. The insertion of a fluorous benzyl protecting group enhances the efficiency of the synthesis (Figure Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7000 / 7003

页数：4

共 37 条

[1] Syntheses and CD-spectroscopic investigations of longer-chain β-peptides:: Preparation by solid-phase couplings of single amino acids, dipeptides, and tripeptides [J].

Arvidsson, PI ;

Frackenpohl, J ;

Seebach, D .

HELVETICA CHIMICA ACTA, 2003, 86 (05) :1522-1553

[2] A flow process for the multi-step synthesis of the alkaloid natural product oxomaritidine: a new paradigm for molecular assembly [J].

Baxendale, Ian R. ;

Deeley, Jon ;

Griffiths-Jones, Charlotte M. ;

Ley, Steven V. ;

Saaby, Steen ;

Tranmer, Geoffrey K. .

CHEMICAL COMMUNICATIONS, 2006, (24) :2566-2568

[3] Miniaturized continuous flow reaction vessels: influence on chemical reactions [J].

Brivio, M ;

Verboom, W ;

Reinhoudt, DN .

LAB ON A CHIP, 2006, 6 (03) :329-344

[4] Peptide synthesis via amino acid halides [J].

Carpino, LA ;

Beyermann, M ;

Wenschuh, H ;

Bienert, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) :268-274

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

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

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

[6]

Curran DP, 2001, SYNLETT, P1488

[7] Fluorous synthesis with fewer fluorines (light fluorous synthesis): separation of tagged from untagged products by solid-phase extraction with fluorous reverse-phase silica gel [J].

Curran, DP ;

Luo, ZY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) :9069-9072

[8] A novel, base-labile fluorous amine protecting group: synthesis and use as a tag in the purification of synthetic peptides [J].

de Visser, PC ;

van Helden, M ;

Filippov, DV ;

van der Marel, GA ;

Drijfhout, JW ;

van Boom, JH ;

Noort, D ;

Overkleeft, HS .

TETRAHEDRON LETTERS, 2003, 44 (50) :9013-9016

[9]

Ehrfeld W., 2000, Microreactors: new technology for modern chemistry, DOI DOI 10.1002/3527601953

[10]

Erdélyi M, 2002, SYNTHESIS-STUTTGART, P1592

← 1 2 3 4 →