A highly convergent synthesis of a complex oligosaccharide derived from group B type III Streptococcus

被引:40
作者
Demchenko, AV [1 ]
Boons, GJ [1 ]
机构
[1] Univ Georgia, Complex Carbohydrate Res Ctr, Athens, GA 30602 USA
关键词
D O I
10.1021/jo001477w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of a heptasaccharide derived from group B type III Streptococcus carrying an artificial spacer (1) is described. Rapid assembly of a protected heptasaccharide (16a) is accomplished from readily available building blocks 2-5 without a single protecting group manipulation between glycosylation steps. The synthetic strategy may be applied to the assembly of other branched complex oligosaccharides. The deprotected heptasaccharide 1 was coupled to a poly[N-(acryloyloxy)succinimide, and the resulting material will be used for the development of an ELISA assay to detect antibodies against GBS, type III in pregnant women.
引用
收藏
页码:2547 / 2554
页数:8
相关论文
共 27 条
[11]  
Demchenko AV, 1999, CHEM-EUR J, V5, P1278, DOI 10.1002/(SICI)1521-3765(19990401)5:4<1278::AID-CHEM1278>3.3.CO
[12]  
2-C
[13]  
FRASERREID B, 1992, SYNLETT, P927
[14]   THIOGLYCOSIDES AS GLYCOSYLATING AGENTS IN OLIGOSACCHARIDE SYNTHESIS [J].
FUGEDI, P ;
GAREGG, PJ ;
LONN, H ;
NORBERG, T .
GLYCOCONJUGATE JOURNAL, 1987, 4 (02) :97-108
[15]   SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES .19. A FACILE, LARGE-SCALE PREPARATION OF THE METHYL 2-THIOGLYCOSIDE OF N-ACETYLNEURAMINIC ACID, AND ITS USEFULNESS FOR THE ALPHA-STEREOSELECTIVE SYNTHESIS OF SIALOGLYCOSIDES [J].
HASEGAWA, A ;
OHKI, H ;
NAGAHAMA, T ;
ISHIDA, H ;
KISO, M .
CARBOHYDRATE RESEARCH, 1991, 212 :277-281
[16]   2-(TRIMETHYLSILYL)ETHYL GLYCOSIDES .3. SYNTHESIS, ANOMERIC DEBLOCKING, AND TRANSFORMATION INTO 1,2-TRANS 1-O-ACYL SUGARS [J].
JANSSON, K ;
AHLFORS, S ;
FREJD, T ;
KIHLBERG, J ;
MAGNUSSON, G ;
DAHMEN, J ;
NOORI, G ;
STENVALL, K .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5629-5647
[17]   IMMUNODETERMINANT SPECIFICITY OF HUMAN IMMUNITY TO TYPE-III GROUP-B STREPTOCOCCUS [J].
KASPER, DL ;
BAKER, CJ ;
BALTIMORE, RS ;
CRABB, JH ;
SCHIFFMAN, G ;
JENNINGS, HJ .
JOURNAL OF EXPERIMENTAL MEDICINE, 1979, 149 (02) :327-339
[18]   SYNTHESIS OF THE CAPSULAR POLYSACCHARIDE OF STREPTOCOCCUS-PNEUMONIAE TYPE-14 [J].
KOCHETKOV, NK ;
NIFANTEV, NE ;
BACKINOWSKY, LV .
TETRAHEDRON, 1987, 43 (13) :3109-3121
[19]   SYNTHESIS OF A TRI-SACCHARIDE AND A HEPTA-SACCHARIDE WHICH CONTAIN ALPHA-L-FUCOPYRANOSYL GROUPS AND ARE PART OF THE COMPLEX TYPE OF CARBOHYDRATE MOIETY OF GLYCOPROTEINS [J].
LONN, H .
CARBOHYDRATE RESEARCH, 1985, 139 (JUN) :105-113
[20]   STUDIES RELATED TO SYNTHESIS OF GLYCOPHOSPHATIDYLINOSITOL MEMBRANE-BOUND PROTEIN ANCHORS .6. CONVERGENT ASSEMBLY OF SUBUNITS [J].
MADSEN, R ;
UDODONG, UE ;
ROBERTS, C ;
MOOTOO, DR ;
KONRADSSON, P ;
FRASERREID, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (05) :1554-1565