A new photolabile carboxyl protecting group for native chemical ligation

被引：2

作者：

Briand, Benoit ^{[1
]}

Kotzur, Nico ^{[1
]}

Hagen, Volker ^{[1
]}

Beyermann, Michael ^{[1
]}

机构：

[1] Leibniz Inst Mol Pharmacol, D-13125 Berlin, Germany

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 01期

关键词：

D O I：

10.1016/j.tetlet.2007.11.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Native chemical ligation (NCL) at Glu-Cys sites requires carboxyl protection that is compatible with the chemistry used for assembling the peptides. In the case of Fmoc-chemistry our novel BCMACM-group is particularly suitable for NCL because of the good solubility in aqueous solvent systems and mild conditions of photolytic removal. (C) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：85 / 87

页数：3

相关论文

共 17 条

[1]

Bang D., 2005, ANGEW CHEM, V117, P3920

[2]

BOCHET CG, 2002, J CHEM SOC P1, V2, P125

[3]

Cammish LE, 2000, PRACT APPROACH SER, V222, P277

[4] A NOVEL 4-AMINOBENZYL ESTER-BASED CARBOXY-PROTECTING GROUP FOR SYNTHESIS OF ATYPICAL PEPTIDES BY FMOC-BU(T) SOLID-PHASE CHEMISTRY [J].

CHAN, WC ;

BYCROFT, BW ;

EVANS, DJ ;

WHITE, PD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (21) :2209-2210

[5] Synthesis of native proteins by chemical ligation [J].

Dawson, PE ;

Kent, SBH .

ANNUAL REVIEW OF BIOCHEMISTRY, 2000, 69 :923-960

[6]

Eggelkraut-Gottanka R, 2003, TETRAHEDRON LETT, V44, P3551

[7] Brominated 7-hydroxycoumarin-4-ylmethyls: Photolabile protecting groups with biologically useful cross-sections for two photon photolysis [J].

Furuta, T ;

Wang, SSH ;

Dantzker, JL ;

Dore, TM ;

Bybee, WJ ;

Callaway, EM ;

Denk, W ;

Tsien, RY .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (04) :1193-1200

[8] (Coumarin-4-yl)methyl esters as highly efficient, ultrafast phototriggers for protons and their application to acidifying membrane surfaces [J].

Geissler, D ;

Antonenko, YN ;

Schmidt, R ;

Keller, S ;

Krylova, OO ;

Wiesner, B ;

Bendig, J ;

Pohl, P ;

Hagen, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (08) :1195-1198

[9] Protein synthesis by native chemical ligation: Expanded scope by using straightforward methodology [J].

Hackeng, TM ;

Griffin, JH ;

Dawson, PE .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (18) :10068-10073

[10] Coumarinylmethyl esters for ultrafast release of high concentrations of cyclic nucleotides upon one- and two-photon photolysis [J].

Hagen, V ;

Dekowski, B ;

Nache, V ;

Schmidt, R ;

Geissler, D ;

Lorenz, D ;

Eichhorst, J ;

Keller, S ;

Kaneko, H ;

Benndorf, K ;

Wiesner, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7887-7891