Lipase-catalysed regioselective acylations in combination with regioselective glycosylations as a strategy for the synthesis of oligosaccharides: Synthesis of a series of fucosyllactose building blocks

被引：6

作者：

Rencurosi, A

Poletti, L

Russo, G

Lay, L

机构：

[1] Univ Milan, Ctr Interdisciplinare Studi Biomol & Applicaz Ind, CISI, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

[2] CNR, Ist Sci & Tecnol Mol, I-20133 Milan, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 09期

关键词：

oligosaccharides; fucosyllactose; glycosylation; lipase acylation;

D O I：

10.1002/ejoc.200200425

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A family of five regioisomenc protected fucosyllactoses has been synthesised in only 14 overall steps from the easily available benzyllactoside. The adopted strategy combines enzymatic regioselective protection, introduction of ortho-gonal protecting groups and regioselective glycosylations on partially unprotected lactosidic acceptors.

引用

页码：1672 / 1680

页数：9

共 48 条

[11]

FUGEDI P, 2001, 11 EUR CARB S LISB

[12]

Gege C, 2000, CHEM-EUR J, V6, P111, DOI 10.1002/(SICI)1521-3765(20000103)6:1<111::AID-CHEM111>3.0.CO

[13]

2-X

[14]

Geurtsen R, 2002, EUR J ORG CHEM, V2002, P1473, DOI 10.1002/1099-0690(200205)2002:9<1473::AID-EJOC1473>3.0.CO

[15]

2-O

[16] CHEMISTRY OF GLYCOSIDIC LINKAGE - EFFICIENT SYNTHESIS OF 1,2-TRANS-DISACCHARIDES [J].

HANESSIAN, S ;

BANOUB, J .

CARBOHYDRATE RESEARCH, 1977, 53 (01) :C13-C16

[17] SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES .52. SYNTHESIS OF SIALYL LEWIS-X ANALOGS CONTAINING AZIDOALKYL GROUPS AT THE REDUCING END [J].

HASEGAWA, A ;

FUSHIMI, K ;

ISHIDA, H ;

KISO, M .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1993, 12 (08) :1203-1216

[18] 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

[19] RECEPTOR-LIKE GLYCO-COMPOUNDS IN HUMAN-MILK THAT INHIBIT CLASSICAL AND EL-TOR VIBRIO-CHOLERAE CELL ADHERENCE (HEMAGGLUTINATION) [J].

HOLMGREN, J ;

SVENNERHOLM, AM ;

LINDBLAD, M .

INFECTION AND IMMUNITY, 1983, 39 (01) :147-154

[20]

JUNG KH, 1989, LIEBIGS ANN CHEM, P1099

← 1 2 3 4 5 →