Synthesis of glyco(lipo) peptides by liposome-mediated native chemical Ligation

被引:36
作者
Ingale, Sampat [1 ]
Buskas, Therese [1 ]
Boons, Geert-Jan [1 ]
机构
[1] Univ Georgia, Complex Carbohydrate Res Ctr, Athens, GA 30602 USA
关键词
D O I
10.1021/ol062423x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Although native chemical ligation (NCL) is emerging as a powerful method for the assembly of (glyco) peptide building blocks, its applicability is reduced when peptide segments are poorly soluble in aqueous buffer. We have found that incorporating reactants in liposomes allows NCL of lipophilic peptides and lipopeptides. Furthermore, the reaction rates of liposome-mediated NCL are higher than traditional reaction conditions resulting in improved yields.
引用
收藏
页码:5785 / 5788
页数:4
相关论文
共 32 条
[1]   Towards a fully synthetic carbohydrate-based anticancer vaccine: Synthesis and immunological evaluation of a lipidated glycopeptide containing the tumor-associated Tn antigen [J].
Buskas, T ;
Ingale, S ;
Boons, GJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (37) :5985-5988
[2]   Glycopeptides as versatile tools for glycobiology [J].
Buskas, Therese ;
Ingale, Sampat ;
Boons, Geert-Jan .
GLYCOBIOLOGY, 2006, 16 (08) :113R-136R
[3]   Highly efficient stereospecific preparation of Tn and TF building blocks using thioglycosyl donors and the Ph2SO/Tf2O promotor system [J].
Cato, D ;
Buskas, T ;
Boons, GJ .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2005, 24 (4-6) :503-516
[4]   Total chemical synthesis and electrophysiological characterization of mechanosensitive channels from Escherichia coli and Mycobacterium tuberculosis [J].
Clayton, D ;
Shapovalov, G ;
Maurer, JA ;
Dougherty, DA ;
Lester, HA ;
Kochendoerfer, GG .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (14) :4764-4769
[5]  
Danishefsky SJ, 2000, ANGEW CHEM INT EDIT, V39, P836, DOI 10.1002/(SICI)1521-3773(20000303)39:5<836::AID-ANIE836>3.0.CO
[6]  
2-I
[7]   SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].
DAWSON, PE ;
MUIR, TW ;
CLARKLEWIS, I ;
KENT, SBH .
SCIENCE, 1994, 266 (5186) :776-779
[8]   Modulation of reactivity in native chemical ligation through the use of thiol additives [J].
Dawson, PE ;
Churchill, MJ ;
Ghadiri, MR ;
Kent, SBH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (19) :4325-4329
[9]   Synthesis of native proteins by chemical ligation [J].
Dawson, PE ;
Kent, SBH .
ANNUAL REVIEW OF BIOCHEMISTRY, 2000, 69 :923-960
[10]   Exploring and exploiting the therapeutic potential of glycoconjugates [J].
Doores, KJ ;
Gamblin, DP ;
Davis, BG .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (03) :656-665