STRUCTURAL VARIATIONS ON N-ACETYLNEURAMINIC ACID .21. 2,3-DIDEHYDRO-2-DEOXYSIALIC ACIDS STRUCTURALLY VARIED AT C-5 AND THEIR BEHAVIOR TOWARDS THE SIALIDASE FROM VIBRIO-CHOLERAE

被引：0

作者：

SCHREINER, E

ZBIRAL, E

KLEINEIDAM, RG

SCHAUER, R

机构：

[1] UNIV VIENNA,INST ORGAN CHEM,WAHRINGER STR 38,A-1090 VIENNA,AUSTRIA

[2] CHRISTIAN ALBRECHTS UNIV KIEL,INST BIOCHEM,W-2300 KIEL 1,GERMANY

来源：

CARBOHYDRATE RESEARCH | 1991年 / 216卷

关键词：

D O I：

暂无

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：

2,3-Didehydro-2-deoxy-N-trifluoroacetylneuraminic acid (5-trifluoroacetyl-Neu2en) (3) has been synthesised from Neu5Ac2en (1) by hydrazinolysis, to give Neu2en (2), followed by N-trifluoroacetylation. 2,3-Didehydro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (Kdn2en, 8) and 5-azido-2,3-didehydro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (5-azido-5-deoxy-Kdn2en, 9) have been prepared from the acetylated methyl esters of Kdn (4) and 5-azido-5-deoxy-Kdn (5) via Zemplen saponification. The behaviour of the above 2,3-didehydro-2-deoxysialic acids towards Vibrio cholerae sialidase has been investigated.

引用

页码：61 / 66

页数：6

共 8 条

[1] STRUCTURAL VARIATIONS ON N-ACETYLNEURAMINIC ACID .20. SYNTHESIS OF SOME 2,3-DIDEHYDRO-2-DEOXYSIALIC ACIDS STRUCTURALLY VARIED AT C-4 AND THEIR BEHAVIOR TOWARDS SIALIDASE FROM VIBRIO-CHOLERAE
SCHREINER, E
ZBIRAL, E
KLEINEIDAM, RG
SCHAUER, R
LIEBIGS ANNALEN DER CHEMIE, 1991, (02): : 129 - 134
[2] STRUCTURAL VARIATIONS OF N-ACETYLNEURAMINIC ACID .7. SYNTHESIS OF THE C-7-SIDE, C-8-SIDE, AND C-7,8-SIDE CHAIN EPIMERS OF 2-DEOXY-2,3-DIDEHYDRO-N-ACETYLNEURAMINIC ACID AND THEIR BEHAVIOR TOWARDS SIALIDASE FROM VIBRIO-CHOLERAE
ZBIRAL, E
BRANDSTETTER, HH
CHRISTIAN, R
SCHAUER, R
LIEBIGS ANNALEN DER CHEMIE, 1987, (09): : 781 - 786
[3] STRUCTURAL VARIATIONS OF N-ACETYLNEURAMINIC ACID .10. SYNTHESIS OF 2,7-DIDEOXY-2,3-DIDEHYDRO-N-ACETYLNEURAMINIC, 2,8-DIDEOXY-2,3-DIDEHYDRO-N-ACETYLNEURAMINIC, AND 2,9-DIDEOXY-2,3-DIDEHYDRO-N-ACETYLNEURAMINIC AND 2,4,7-TRIDEOXY-2,3-DIDEHYDRO-N-ACETYLNEURAMINIC ACIDS AND THEIR BEHAVIOR TOWARDS SIALIDASE FROM VIBRIO-CHOLERAEM
ZBIRAL, E
SCHREINER, E
CHRISTIAN, R
KLEINEIDAM, RG
SCHAUER, R
LIEBIGS ANNALEN DER CHEMIE, 1989, (02): : 159 - 165
[4] SYNTHESIS OF A PHOSPHONIC ACID ANALOG OF N-ACETYL-2,3-DIDEHYDRO-2-DEOXYNEURAMINIC ACID, AN INHIBITOR OF VIBRIO-CHOLERAE SIALIDASE
VASELLA, A
WYLER, R
HELVETICA CHIMICA ACTA, 1991, 74 (02) : 451 - 463
[5] STRUCTURAL VARIATIONS OF N-ACETYLNEURAMINIC ACID .11. SYNTHESIS OF THE 4-METHYLUMBELLIFERYL 2-ALPHA-GLYCOSIDES OF 7-EPI-N-ACETYLNEURAMINIC, 8-EPI-N-ACETYLNEURAMINIC, AND 7,8-BIS(EPI)-N-ACETYLNEURAMINIC ACIDS, AS WELL AS OF 7-DEOXY-N-ACETYLNEURAMINIC, 8-DEOXY-N-ACETYLNEURAMINIC, 9-DEOXY-N-ACETYLNEURAMINIC, AND 4,7-DIDEOXY-N-ACETYLNEURAMINIC ACIDS AND THEIR BEHAVIOR TOWARDS SIALIDASE FROM VIBRIO-CHOLERAE
ZBIRAL, E
SCHREINER, E
SALUNKHE, MM
SCHULZ, G
KLEINEIDAM, RG
SCHAUER, R
LIEBIGS ANNALEN DER CHEMIE, 1989, (06): : 519 - 526
[6] STRUCTURAL VARIATIONS OF N-ACETYLNEURAMINIC ACID .23. SYNTHESIS OF 2-DEOXY-2HEQ-SIALIC ACID ANALOGS STRUCTURALLY VARIED AT C-4
HARTMANN, M
ZBIRAL, E
LIEBIGS ANNALEN DER CHEMIE, 1991, (08): : 795 - 801
[7] STRUCTURAL VARIATIONS OF N-ACETYLNEURAMINIC ACID .10. SYNTHESIS OF BOTH EPIMERIC 2-DEOXY-N-ACETYLNEURAMINIC ACIDS AND THEIR BEHAVIOR TOWARDS CMP-SIALATE SYNTHETASE-A COMPARISON WITH 2-BETA-METHYLKETOSIDE OF N-ACETYLNEURAMINIC ACID
SCHMID, W
CHRISTIAN, R
ZBIRAL, E
TETRAHEDRON LETTERS, 1988, 29 (30) : 3643 - 3646
[8] Synthesis of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid analogues modified at the C-4 and C-9 positions and their behaviour towards sialidase from influenza virus and pig liver membrane
Ikeda, K
Sano, K
Ito, M
Saito, M
Hidari, K
Suzuki, T
Suzuki, Y
Tanaka, K
CARBOHYDRATE RESEARCH, 2001, 330 (01) : 31 - 41

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