A program for ligation at threonine sites: application to the controlled total synthesis of glycopeptides

被引:101
作者
Chen, Jin [1 ]
Wang, Ping [1 ]
Zhu, Jianglong [1 ]
Wan, Qian [1 ]
Danishefsky, Samuel J. [1 ,2 ]
机构
[1] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10065 USA
[2] Columbia Univ, Dept Chem, New York, NY 10027 USA
基金
美国国家卫生研究院;
关键词
NATIVE CHEMICAL LIGATION; FOLLICLE-STIMULATING-HORMONE; HUMAN PITUITARY-GLANDS; AMINO-ACID SEQUENCE; PROTEIN GLYCOSYLATION; TRIALKYL PHOSPHITES; THIYL RADICALS; GLYCOPROTEIN; DESULFURIZATION; PEPTIDES;
D O I
10.1016/j.tet.2010.01.067
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method by which to accomplish formal threonine ligation has been developed. The method accomplishes ligations of two peptide domains. We have also demonstrated the ability to successfully ligate two independent glycopeptide domains. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2277 / 2283
页数:7
相关论文
共 59 条
[1]   L-VINYLGLYCINE [J].
AFZALIARDAKANI, A ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (24) :4817-4820
[2]   Emerging applications of recombinant human granulocyte-macrophage colony-stimulating factor [J].
Armitage, JO .
BLOOD, 1998, 92 (12) :4491-4508
[3]   Semisynthesis of a Glycosylphosphatidylinositol-Anchored Prion Protein [J].
Becker, Christian F. W. ;
Liu, Xinyu ;
Olschewski, Diana ;
Castelli, Riccardo ;
Seidel, Ralf ;
Seeberger, Peter H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (43) :8215-8219
[4]   Chemical glycobiology [J].
Bertozzi, CR ;
Kiessling, LL .
SCIENCE, 2001, 291 (5512) :2357-2364
[5]   Sugar-assisted ligation for the synthesis of glycopeptides [J].
Brik, Ashraf ;
Wong, Chi-Huey .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (20) :5670-5675
[6]   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
[7]   Antibody domain exchange is an immunological solution to carbohydrate cluster recognition [J].
Calarese, DA ;
Scanlan, CN ;
Zwick, MB ;
Deechongkit, S ;
Mimura, Y ;
Kunert, R ;
Zhu, P ;
Wormald, MR ;
Stanfield, RL ;
Roux, KH ;
Kelly, JW ;
Rudd, PM ;
Dwek, RA ;
Katinger, H ;
Burton, DR ;
Wilson, IA .
SCIENCE, 2003, 300 (5628) :2065-2071
[8]   Native Chemical Ligation at Valine: A Contribution to Peptide and Glycopeptide Synthesis [J].
Chen, Jin ;
Wan, Qian ;
Yuan, Yu ;
Zhu, Jianglong ;
Danishefsky, Samuel J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8521-8524
[9]   Native chemical ligation at phenylalanine [J].
Crich, David ;
Banerjee, Abhisek .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (33) :10064-+
[10]   A QUANTITATIVE IMMUNOCYTOCHEMICAL STUDY OF THE LUTEINIZING-HORMONE AND FOLLICLE-STIMULATING-HORMONE CELLS IN THE ADENOHYPOPHYSIS OF ADULT MALE-RATS AND ADULT FEMALE RATS THROUGHOUT THE ESTROUS-CYCLE [J].
DADA, MO ;
CAMPBELL, GT ;
BLAKE, CA .
ENDOCRINOLOGY, 1983, 113 (03) :970-984