1,5-lactamized sialyl acceptors for various disialoside syntheses: Novel method for the synthesis of glycan portions of Hp-S6 and HLG-2 gangliosides

被引：76

作者：

Ando, H

Koike, Y

Koizumi, S

Ishida, H

Kiso, M

机构：

[1] Gifu Univ, Div Instrumental Anal, Life Sci Res Ctr, Gifu 5011193, Japan

[2] Gifu Univ, Dept Appl Bioorgan Chem, Fac Appl Biol Sci, Gifu 5011193, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 41期

关键词：

gangliosides; glycosylation; lactams; sialic acids;

D O I：

10.1002/anie.200501608

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A dramatic enhancement of the reactivity of the C4- and C8-hydroxy groups of sialic acid has been demonstrated by 1,5-lactam bridging. Sialyl-α(2→4)sialoside and sialyl-α(2→8) sialoside were made available in high yields through direct sialylation (see scheme). Furthermore, the glycan parts of the new gangliosides Hp-s6 and HLG-2 were synthesized for the first time. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

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收藏

页码：6759 / 6763

页数：5

相关论文

共 33 条

[1] Extending the possibility of an N-Troc-protected sialic acid donor toward variant sialo-glycoside synthesis [J].

Ando, H ;

Koike, Y ;

Ishida, H ;

Kiso, M .

TETRAHEDRON LETTERS, 2003, 44 (36) :6883-6886

[2] Recent advances in O-sialylation [J].

Boons, GJ ;

Demchenko, AV .

CHEMICAL REVIEWS, 2000, 100 (12) :4539-+

[3] 8-O-sialylation of neuraminic acid [J].

Castro-Palomino, JC ;

Tsvetkov, YE ;

Schmidt, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5434-5440

[4]

De Meo C, 2001, J ORG CHEM, V66, P5490

[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] REDUCTIVE RING OPENINGS OF CARBOHYDRATE BENZYLIDENE ACETALS USING BORANE-TRIMETHYLAMINE AND ALUMINUM-CHLORIDE - REGIOSELECTIVITY AND SOLVENT DEPENDENCE [J].

EK, M ;

GAREGG, PJ ;

HULTBERG, H ;

OSCARSON, S .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1983, 2 (03) :305-311

[8] SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES .25. REACTIVITY OF GLYCOSYL PROMOTERS IN ALPHA-GLYCOSYLATION OF N-ACETYL-NEURAMINIC ACID WITH THE PRIMARY AND SECONDARY HYDROXYL-GROUPS IN THE SUITABLY PROTECTED GALACTOSE AND LACTOSE DERIVATIVES [J].

HASEGAWA, A ;

NAGAHAMA, T ;

OHKI, H ;

HOTTA, K ;

ISHIDA, H ;

KISO, M .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1991, 10 (03) :493-498

[9] DETERMINATION OF THE BETA-ANOMERIC CONFIGURATION OF CYTIDINE 5'-MONOPHOSPHO-N-ACETYLNEURAMINIC ACID BY C-13 NMR-SPECTROSCOPY [J].

HAVERKAMP, J ;

SPOORMAKER, T ;

DORLAND, L ;

VLIEGENTHART, JFG ;

SCHAUER, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :4851-4853

[10] 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

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