Sialidase substrate specificity studies using chemoenzymatically synthesized sialosides containing C5-modified sialic acids

被引：44

作者：

Cao, Hongzhi ^{[1
]}

Li, Yanhong ^{[1
]}

Lau, Kam ^{[1
]}

Muthana, Saddam ^{[1
]}

Yu, Hai ^{[1
]}

Cheng, Jiansong ^{[1
]}

Chokhawala, Harshal A. ^{[1
]}

Sugiarto, Go ^{[1
]}

Zhang, Lei ^{[1
]}

Chen, Xi ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 24期

关键词：

N-ACETYLNEURAMINIC ACID; CARBOHYDRATE SYNTHESIS; TERMINAL ALKYNES; AZIDES; CYCLOADDITIONS; DERIVATIVES; DIVERSITY; LIBRARIES; LIGATION; ALDOLASE;

D O I：

10.1039/b916305k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

para-Nitrophenol-tagged sialyl galactosides containing sialic acid derivatives in which the C5 hydroxyl group of sialic acids was systematically substituted with a hydrogen, a fluorine, a methoxyl or an azido group were successfully synthesized using an efficient chemoenzymatic approach. These compounds were used as valuable probes in high-throughput screening assays to study the importance of the C5 hydroxyl group of sialic acid in the recognition and the cleavage of sialoside substrates by bacterial sialidases.

引用

收藏

页码：5137 / 5145

页数：9

相关论文

共 30 条

[1] Metal catalyzed diazo transfer for the synthesis of azides from amines [J].

Alper, PB ;

Hung, SC ;

Wong, CH .

TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032

[2] Chemical diversity in the sialic acids and related α-keto acids:: An evolutionary perspective [J].

Angata, T ;

Varki, A .

CHEMICAL REVIEWS, 2002, 102 (02) :439-469

[3] SCOPE AND LIMITATIONS OF THE ALDOL CONDENSATION CATALYZED BY IMMOBILIZED ACYLNEURAMINATE PYRUVATE LYASE [J].

AUGE, C ;

BOUXOM, B ;

CAVAYE, B ;

GAUTHERON, C .

TETRAHEDRON LETTERS, 1989, 30 (17) :2217-2220

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

Boons, GJ ;

Demchenko, AV .

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

[5] A new method for the synthesis of fluoro-carbohydrates and glycosides using selectfluor [J].

Burkart, MD ;

Zhang, ZY ;

Hung, SC ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) :11743-11746

[6] High-throughput substrate specificity studies of sialidases by using chemoenzymatically synthesized sialoside libraries [J].

Chokhawala, Harshal A. ;

Yu, Hai ;

Chen, Xi .

CHEMBIOCHEM, 2007, 8 (02) :194-201

[7]

COMB DG, 1960, J BIOL CHEM, V235, P2529

[8] Glycobiology: Toward understanding the function of sugars [J].

Dwek, RA .

CHEMICAL REVIEWS, 1996, 96 (02) :683-720

[9] Identification of 2-keto-3-deoxy-D-glycero-D-galactonononic acid (KDN, deaminoneuraminic acid) residues in mammalian tissues and human lung carcinoma cells - Chemical evidence of the occurrence of KDN glycoconjugates in mammals [J].

Inoue, S ;

Kitajima, K ;

Inoue, Y .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (40) :24341-24344

[10] Microbial glycosyltransferases for carbohydrate synthesis:: α-2,3-sialyltransferase from Neisseria gonorrheae [J].

Izumi, M ;

Shen, GJ ;

Wacowich-Sgarbi, S ;

Nakatani, T ;

Plettenburg, O ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10909-10918