Total synthesis of a sialylated and sulfated oligosaccharide from O-linked glycoproteins

被引：17
作者：
Xia, J [1 ]
Piskorz, CF [1 ]
Alderfer, JL [1 ]
Locke, RD [1 ]
Matta, KL [1 ]
机构：
[1] Roswell Pk Canc Inst, Buffalo, NY 14263 USA
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 16期
关键词：
D O I：
10.1016/S0040-4039(00)00261-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of a sialylated and sulfated oligosaccharide 1 representative of a structure occurring in respiratory mucins has been accomplished. Our strategy depends upon the employment of 2-naphthymethyl (NAP) protection for hydroxyl functions. Choice of the well-defined sialyl donor 15 was made because of its enhanced reactivity over the parent compound 14 for glycosylation. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2773 / 2776
页数：4
相关论文
共 32 条
[1]   Sulfated Lewis X determinants as a major structural motif in glycans from LS174T-HM7 human colon carcinoma mucin [J].
Capon, C ;
Wieruszeski, JM ;
Lemoine, J ;
Byrd, JC ;
Leffler, H ;
Kim, YS .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (51) :31957-31968
[2]  
CHANDRASEKARAN EV, 1992, GLYCOCONJ J, V9, P23806
[3]   APPLICATION OF GLYCALS TO THE SYNTHESIS OF OLIGOSACCHARIDES - CONVERGENT TOTAL SYNTHESES OF THE LEWIS-X TRISACCHARIDE SIALYL-LEWIS-X ANTIGENIC DETERMINANT AND HIGHER CONGENERS [J].
DANISHEFSKY, SJ ;
GERVAY, J ;
PETERSON, JM ;
MCDONALD, FE ;
KOSEKI, K ;
GRIFFITH, DA ;
ORIYAMA, T ;
MARSDEN, SP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (07) :1940-1953
[4]   REGIOSELECTIVE MANIPULATION OF HYDROXYL-GROUPS VIA ORGANOTIN DERIVATIVES [J].
DAVID, S ;
HANESSIAN, S .
TETRAHEDRON, 1985, 41 (04) :643-663
[5]  
Demchenko AV, 1999, CHEM-EUR J, V5, P1278, DOI 10.1002/(SICI)1521-3765(19990401)5:4<1278::AID-CHEM1278>3.3.CO
[6]  
2-C
[7]   A novel and versatile glycosyl donor for the preparation of glycosides of N-Acetylneuraminic acid [J].
Demchenko, AV ;
Boons, GJ .
TETRAHEDRON LETTERS, 1998, 39 (19) :3065-3068
[8]   Towards oligosaccharide libraries: A study of the random galactosylation of unprotected N-acetylglucosamine [J].
Ding, YL ;
Labbe, J ;
Kanie, O ;
Hindsgaul, O .
BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (05) :683-692
[9]   Glycobiology: Toward understanding the function of sugars [J].
Dwek, RA .
CHEMICAL REVIEWS, 1996, 96 (02) :683-720
[10]   Total synthesis of VIM-2 ganglioside isolated from human chronic myelogenous leukemia cells [J].
Ehara, T ;
Kameyama, A ;
Yamada, Y ;
Ishida, H ;
Kiso, M ;
Hasegawa, A .
CARBOHYDRATE RESEARCH, 1996, 281 (02) :237-252
1234