HYDROLYSIS OF THE GLCNAC OXAZOLINE - DEAMIDATION AND ACYL REARRANGEMENT

被引：16

作者：

JHA, R ^{[1
]}

DAVIS, JT ^{[1
]}

机构：

[1] UNIV MARYLAND, DEPT CHEM & BIOCHEM, COLLEGE PK, MD 20742 USA

来源：

CARBOHYDRATE RESEARCH | 1995年 / 277卷 / 01期

关键词：

GLCNAC OXAZOLINE; DEAMIDATION; ACYL REARRANGEMENT;

D O I：

10.1016/0008-6215(95)00222-F

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The specific deamidation of 2-acetamido-1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose is achieved by p-toluenesulfonic acid-promoted hydrolysis of 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-d]-2-oxazoline 2 to give quantitative formation of the 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-alpha-D-glucopyranose p-toluenesulfonate (5d). This two-step procedure provides an amino sugar which may be readily acylated to give novel glycoconjugates. Alternatively, base-catalyzed O-1 --> N-2 acyl rearrangement of the amino tosylate 5d gives the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranose 4 as a 9:1 mixture of alpha and beta anomers. Thus, hydrolysis of GlcNAc oxazoline 2 gives the amino-ester 5 as the kinetic product and the amido-alcohol 4 as the thermodynamic product.

引用

页码：125 / 134

页数：10

共 26 条

[1] A NOVEL, REGIOSELECTIVE AND HIGHLY STEREOSELECTIVE ANOMERIC DEACETYLATION OF 2-AMINOSUGAR DERIVATIVES [J].

AVALOS, M ;

BABIANO, R ;

CINTAS, P ;

JIMENEZ, JL ;

PALACIOS, JC ;

VALENCIA, C .

TETRAHEDRON LETTERS, 1993, 34 (08) :1359-1362

[2] STRUCTURES OF NODULATION FACTORS FROM THE NITROGEN-FIXING SOYBEAN SYMBIONT RHIZOBIUM-FREDII USDA257 [J].

BECFERTE, MP ;

KRISHNAN, HB ;

PROME, D ;

SAVAGNAC, A ;

PUEPPKE, SG ;

PROME, JC .

BIOCHEMISTRY, 1994, 33 (39) :11782-11788

[3] MILD CONDITIONS FOR THE PREPARATION OF HIGH-MANNOSE OLIGOSACCHARIDE OXAZOLINES - ENTRY POINT FOR BETA-GLYCOSIDE AND NEOGLYCOPROTEIN SYNTHESES(1) [J].

COLON, M ;

STAVESKI, MM ;

DAVIS, JT .

TETRAHEDRON LETTERS, 1991, 32 (35) :4447-4450

[4] STEREOELECTRONIC CONTROL IN CLEAVAGE OF TETRAHEDRAL INTERMEDIATES IN HYDROLYSIS OF ESTERS AND AMIDES [J].

DESLONGCHAMPS, P .

TETRAHEDRON, 1975, 31 (20) :2463-2490

[5] SELECTIVE CLEAVAGE OF ANOMERIC ACETYL GROUPS OF ACETYLATED GLYCOSYL RESIDUES BY HYDRAZINE [J].

EXCOFFIER, G ;

GAGNAIRE, D ;

UTILLE, JP .

CARBOHYDRATE RESEARCH, 1975, 39 (02) :368-373

[6]

HANESSIA.S, 1967, TETRAHEDRON LETT, P1549

[7]

HANESSIAN S, 1968, METHODS CARBOHYDR CH, V23, P367

[8] ENZYMES IN CARBOHYDRATE SYNTHESIS - LIPASE-CATALYZED SELECTIVE ACYLATION AND DEACYLATION OF FURANOSE AND PYRANOSE DERIVATIVES [J].

HENNEN, WJ ;

SWEERS, HM ;

WANG, YF ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :4939-4945

[9]

HOOK M, 1984, ANNU REV BIOCHEM, V53, P847

[10] SPECIFICALLY DEUTERATED ACETYLATED DERIVATIVES OF 2-AMINO-2-DEOXY-D-GLUCOSE . NUCLEAR MAGNETIC RESONANCE STUDIES ON MIGRATION OF ACETYL GROUPS [J].

HORTON, D ;

MAST, WE ;

PHILIPS, KD .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (05) :1471-&

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