Bicyclic diazasugars 2. Synthesis and structures of L-arabinose and D-ribose analogues

被引：10

作者：

Berges, DA ^{[1
]}

Hong, LW ^{[1
]}

Dalley, NK ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1998年 / 54卷 / 20期

关键词：

aminals; carbohydrate mimetics; diaza compounds; enzyme inhibitors; X-ray crystal structures;

D O I：

10.1016/S0040-4020(98)00249-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic diazasugar analogues of L-arabinose and D-ribose have been prepared and characterized by x-ray crystallography and NMR spectroscopy. The crystalline arabinose analogue is the beta-anomer in the ring-flipped C-1(4) conformation (7), but in D2O solution this is a minor component with the major being the cr-anomer in the C-4(1) conformation(6). The crystalline ribose analogue is the beta-anomer in the C-4(1) conformation (10) which is also the major component in D2O solution and is accompanied by a minor form which is probably the alpha-anomer in the ring-nipped C-1(4) conformation (11). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5097 / 5104

页数：8

共 17 条

[1] THE STRUCTURE OF NAGSTATIN, A NEW INHIBITOR OF N-ACETYL-BETA-D-GLUCOSAMINIDASE [J].

AOYAMA, T ;

NAGANAWA, H ;

SUDA, H ;

UOTANI, K ;

AOYAGI, T ;

TAKEUCHI, T .

JOURNAL OF ANTIBIOTICS, 1992, 45 (09) :1557-1558

[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] BETA-L-ARABINOSIDASE FROM CAJANUS-INDICUS - NEW ENZYME [J].

DEY, PM .

BIOCHIMICA ET BIOPHYSICA ACTA, 1973, 302 (02) :393-398

[4] FURTHER CHARACTERIZATION OF BETA-L-ARABINOSIDASE FROM CAJANUS-INDICUS [J].

DEY, PM .

BIOCHIMICA ET BIOPHYSICA ACTA, 1983, 746 (1-2) :8-13

[5]

Elbein A D, 1991, Semin Cell Biol, V2, P309

[6] GLYCOSIDASE INHIBITORS - INHIBITORS OF N-LINKED OLIGOSACCHARIDE PROCESSING [J].

ELBEIN, AD .

FASEB JOURNAL, 1991, 5 (15) :3055-3063

[7]

FLEET GWJ, 1987, TOPICS MED CHEM, P149

[8]

Goss PE, 1995, CLIN CANCER RES, V1, P935

[9] GLYCOSYLATION INHIBITORS IN BIOLOGY AND MEDICINE [J].

JACOB, GS .

CURRENT OPINION IN STRUCTURAL BIOLOGY, 1995, 5 (05) :605-611

[10]

KAUSHAL GP, 1994, METHOD ENZYMOL, V230, P316

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