Chemoenzymatic synthesis of CD52 glycoproteins carrying native N-glycans

被引:39
作者
Li, HG [1 ]
Singh, S [1 ]
Zeng, Y [1 ]
Song, HJ [1 ]
Wang, LX [1 ]
机构
[1] Univ Maryland, Inst Biotechnol, Inst Human Virol, Baltimore, MD 21201 USA
关键词
glycopeptide; glycoprotein; CD52; chemoenzymatic synthesis;
D O I
10.1016/j.bmcl.2004.12.066
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A facile synthesis of homogeneous CD52 glycoproteins carrying native N-glycans was achieved using an endolycosidase-catalyzed oligosaccharide transfer as the key step. The synthesis consists of two steps: the solid phase synthesis of GlcNAc-CD52 and the transfer of a high-mannose type or complex type N-glycan from Man(9)GlcNAc(2) Asn or a sialglycopeptide to the GlcNAc-CD52, under the catalysis of the endo-beta-N-acetylglucosaminidases from Arthrobacter (Endo-A) and Mucor hiemalis (Endo-M), respectively. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:895 / 898
页数:4
相关论文
共 21 条
[1]  
Domagala A, 2001, MED SCI MONITOR, V7, P325
[2]   Glycobiology: Toward understanding the function of sugars [J].
Dwek, RA .
CHEMICAL REVIEWS, 1996, 96 (02) :683-720
[3]   Homogeneous glycopeptides and glycoproteins for biological investigation [J].
Grogan, MJ ;
Pratt, MR ;
Marcaurelle, LA ;
Bertozzi, CR .
ANNUAL REVIEW OF BIOCHEMISTRY, 2002, 71 :593-634
[4]   Solid-phase synthesis of the CD52 glycopeptide carrying an N-linked core pentasaccharide structure [J].
Guo, ZW ;
Nakahara, Y ;
Nakahara, Y ;
Ogawa, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1464-1466
[5]   Intracellular functions of N-linked glycans [J].
Helenius, A ;
Aebi, M .
SCIENCE, 2001, 291 (5512) :2364-2369
[6]   Synthesis of glycopeptides containing carbohydrate and peptide recognition motifs [J].
Herzner, H ;
Reipen, T ;
Schultz, M ;
Kunz, H .
CHEMICAL REVIEWS, 2000, 100 (12) :4495-4537
[7]   Synthesis of a glycopeptide containing oligosaccharides: Chemoenzymatic synthesis of eel calcitonin analogues having natural N-linked oligosaccharides [J].
Mizuno, M ;
Haneda, K ;
Iguchi, R ;
Muramoto, I ;
Kawakami, T ;
Aimoto, S ;
Yamamoto, K ;
Inazu, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :284-290
[8]   Probing the effect of the outer saccharide residues of N-linked glycans on peptide conformation [J].
O'Connor, SE ;
Pohlmann, J ;
Imperiali, B ;
Saskiawan, I ;
Yamamoto, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) :6187-6188
[9]   Chemoselective ligation applied to the synthesis of a biantennary N-linked glycoform of CD52 [J].
Pratt, MR ;
Bertozzi, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6149-6159
[10]   Glycosylation and the immune system [J].
Rudd, PM ;
Elliott, T ;
Cresswell, P ;
Wilson, IA ;
Dwek, RA .
SCIENCE, 2001, 291 (5512) :2370-2376