Bicyclic azasugars containing a glycosidic heteroatom: D-xylose analogues

被引：17

作者：

Berges, DA ^{[1
]}

Fan, JM ^{[1
]}

Devinck, S ^{[1
]}

Liu, NN ^{[1
]}

Dalley, NK ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

TETRAHEDRON | 1999年 / 55卷 / 22期

关键词：

carbohydrate mimetics; aza compounds; enzyme inhibitors; X-ray crystal structures;

D O I：

10.1016/S0040-4020(99)00335-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic azasugar analogues of D-xylose containing a glycosidic heteroatom have been prepared and characterized by X-ray crystallography and NMR spectroscopy. Compounds in which the glycosidic heteroatom is N (substituted with H or CH3), O, and S have been prepared, and the ring fused to the azasugar ring has been 5- or 6-membered; 7-membered analogues are either unstable or do not form. alpha-Anomers are present when the glycosidic heteroatom is O or S but not N, and even then they are less favored than the corresponding beta-anomers. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：6759 / 6770

页数：12

共 16 条

[1] Bicyclic diazasugars 2. Synthesis and structures of L-arabinose and D-ribose analogues [J].

Berges, DA ;

Hong, LW ;

Dalley, NK .

TETRAHEDRON, 1998, 54 (20) :5097-5104

[2] (7R,8S,9S,9aR)-octahydro-7,8,9-trihydroxy-2H-pyrido[1,2-a]pyrimidine:: A bicyclic diazasugar [J].

Berges, DA ;

Ridges, MD ;

Dalley, NK .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (02) :391-392

[3]

deRaadt A, 1997, TOP CURR CHEM, V187, P157

[4]

Eliel E. L., 1994, Stereochemistry of Organic Compounds, P696

[5]

INOUYE S, 1968, TETRAHEDRON, V23, P2125

[6] STRUCTURE OF KIFUNENSINE, A NEW IMMUNOMODULATOR ISOLATED FROM AN ACTINOMYCETE [J].

KAYAKIRI, H ;

TAKASE, S ;

SHIBATA, T ;

OKAMOTO, M ;

TERANO, H ;

HASHIMOTO, M ;

TADA, T ;

KODA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4015-4016

[7]

KIRBY AJ, 1983, ANOMERIC EFFECT RELA, P22

[8] SYNTHESIS OF 5-AMINO-5-DEOXY-D-MANNOPYRANOSE AND 1,5-DI-DEOXY-1,5-IMINO-D-MANNITOL, AND INHIBITION OF ALPHA-D-MANNOSIDASES AND BETA-D-MANNOSIDASES [J].

LEGLER, G ;

JULICH, E .

CARBOHYDRATE RESEARCH, 1984, 128 (01) :61-72

[9]

Lemieux R. U., 1979, ANOMERIC EFFECT, V87, P17, DOI DOI 10.1021/BK-1979-0087.CH002

[10] A facile route to diastereomerically pure analogues of castanospermine and australine. [J].

Marek, D ;

Wadouachi, A ;

Uzan, R ;

Beaupere, D ;

Nowogrocki, G ;

Laplace, G .

TETRAHEDRON LETTERS, 1996, 37 (01) :49-52

← 1 2 →