Nucleophilic Catalysis of Carbohydrate Oxime Formation by Anilines

被引：69

作者：

Thygesen, Mikkel B. ^{[1
]}

Munch, Henrik ^{[1
]}

Sauer, Jorgen ^{[1
,2
]}

Clo, Emiliano ^{[1
]}

Jorgensen, Malene R. ^{[3
]}

Hindsgaul, Ole ^{[3
]}

Jensen, Knud J. ^{[1
,2
]}

机构：

[1] Univ Copenhagen, IGM Bioorgan Chem, Fac Life Sci, DK-1871 Frederiksberg, Denmark

[2] Ctr Carbohydrate Recognit & Signalling, DK-2500 Valby, Denmark

[3] Carlsberg Lab, DK-2500 Valby, Denmark

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 05期

基金：

新加坡国家研究基金会;

关键词：

CHEMICAL TOOLS; IMMOBILIZATION; GLYCOPEPTIDES; MUTAROTATIONS; SEMICARBAZONE; RECOGNITION; GLYCOMICS; LIGATION; CAPTURE; GLYCANS;

D O I：

10.1021/jo902425v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chemoselective formation of glycoconjugates from unprotected protected glycans is needed to further develop chemical biology involving glycans. Carbohydrate oxime formation is often slow, and organocatalysis by anilines would be highly promising Here, we present that carbohydrate oxime formation can be catalyzed with up to 20-fold increases in overall reaction rate at 100 mM aniline. Application of this methodology provided access to complex glycoconjugates.

引用

页码：1752 / 1755

页数：4

共 38 条

[1] Improved Characterization of Nod Factors and Genetically Based Variation in LysM Receptor Domains Identify Amino Acids Expendable for Nod Factor Recognition in Lotus spp. [J].

Bek, Anita S. ;

Sauer, Jorgen ;

Thygesen, Mikkel B. ;

Duus, Jens O. ;

Petersen, Bent O. ;

Thirup, Soren ;

James, Euan ;

Jensen, Knud J. ;

Stougaard, Jens ;

Radutoiu, Simona .

MOLECULAR PLANT-MICROBE INTERACTIONS, 2010, 23 (01) :58-66

[2] Chemical glycobiology [J].

Bertozzi, CR ;

Kiessling, LL .

SCIENCE, 2001, 291 (5512) :2357-2364

[3] TRANSGLYCOSYLATION OF N-ARYLGLYCOSYLAMINES [J].

BOGNAR, R ;

NANASI, P .

JOURNAL OF THE CHEMICAL SOCIETY, 1955, :189-193

[4] TRANSGLUCOSYLATION OF AROMATIC N-GLUCOSIDES [J].

BOGNAR, R ;

NANASI, P .

NATURE, 1953, 171 (4350) :475-476

[5] One-pot stereoselective synthesis of β-N-aryl-glycosides by N-glycosylation of aromatic amines:: application to the synthesis of tumor-associated carbohydrate antigen building blocks [J].

Bridiau, Nicolas ;

Benmansour, Moulay ;

Legoy, Marie Dominique ;

Maugard, Thierry .

TETRAHEDRON, 2007, 63 (19) :4178-4183

[6] MECHANISM OF HYDROLYSIS OF N-ARYL-D-GLUCOSYLAMINES [J].

CAPON, B ;

CONNETT, BE .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (AUG) :4497-&

[7] Synthesis of glycopeptides and lipopeptides by chemoselective ligation [J].

Cervigni, SE ;

Dumy, P ;

Mutter, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (11) :1230-1232

[8] Chemoselective Reagents for Covalent Capture and Display of Glycans in Microarrays [J].

Clo, Emiliano ;

Blixt, Ola ;

Jensen, Knud J. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (03) :540-554

[9] NUCLEOPHILIC CATALYSIS OF SEMICARBAZONE FORMATION BY ANILINES [J].

CORDES, EH ;

JENCKS, WP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :826-&

[10] Nucleophilic catalysis of oxime ligation [J].

Dirksen, Anouk ;

Hackeng, Tilman M. ;

Dawson, Philip E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) :7581-7584

← 1 2 3 4 →