SYNTHESIS AND CHARACTERIZATION OF FURANOSE AND PYRANOSE DERIVATIVES OF 3-DEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID (KDN)

被引：0

作者：

NAKAMURA, M ^{[1
]}

TAKAYANAGI, H ^{[1
]}

FURUHATA, K ^{[1
]}

OGURA, H ^{[1
]}

机构：

[1] KITASATO UNIV, FAC PHARMACEUT SCI, MINATO KU, TOKYO 108, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1992年 / 40卷 / 04期

关键词：

KDN; ANOMERIC EQUILIBRIUM; FURANOSE; X-RAY CRYSTAL ANALYSIS; H-1-NMR;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The products of Fischer's methyl glycosylation of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) revealed existence of an the anomeric equilibrium between alpha,beta-furanose and alpha,beta-pyranose of KDN. In spite of the anomeric equilibrium, peracetylation of KDN and its derivatives by acetic anhydride with pyridine gave only alpha- and beta-pyranose derivatives. The obtained methyl glycosides and hexa-O-acetyl derivatives were characterized by X-ray, nuclear magnetic resonance and circular dichroism spectral analyses.

引用

页码：879 / 885

页数：7

共 50 条

[1] A novel glycosylation of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via in situ pyranose-furanose rearrangement
Sun, XL
Kai, T
Fujita, S
Takayanagi, H
Furuhata, K
CHEMICAL & PHARMACEUTICAL BULLETIN, 1997, 45 (05) : 795 - 798
[2] A NOVEL SIALIDASE CAPABLE OF CLEAVING 3-DEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID (KDN)
LI, YT
YUZIUK, JA
LI, SC
NEMATALLA, A
HASEGAWA, A
KIMURA, M
NAKAGAWA, H
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1994, 310 (01) : 243 - 246
[3] STUDIES ON SIALIC ACIDS .28. SYNTHESIS OF DISACCHARIDE NUCLEOSIDE DERIVATIVES OF 3-DEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID (KDN)
NAKAMURA, M
FUJITA, S
OGURA, H
CHEMICAL & PHARMACEUTICAL BULLETIN, 1993, 41 (01) : 21 - 25
[4] Reaction products from Fischer's methylation of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN)
Kai, T
Sun, XL
Tanaka, M
Takayanagi, H
Furuhata, K
CHEMICAL & PHARMACEUTICAL BULLETIN, 1996, 44 (01) : 208 - 211
[5] First total synthesis of (+)-3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) from a non-carbohydrate source
Banwell, M
De Savi, C
Watson, K
CHEMICAL COMMUNICATIONS, 1998, (11) : 1189 - 1190
[6] Formal synthesis of (+)3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via desymmetrization by ring-closing metathesis
Burke, SD
Voight, EA
ORGANIC LETTERS, 2001, 3 (02) : 237 - 240
[7] A CONCISE CHEMICAL SYNTHESIS OF (+)-3-DEOXY-D-GLYCERO-D-GALACTO-NONULOSONIC ACID (KDN)
CHAN, TH
LI, CJ
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (10) : 747 - 748
[8] CONVENIENT SYNTHESES OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) AND 3-DEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID (KDN) DERIVATIVES FROM D-MANNOSE
SATO, K
MIYATA, T
TANAI, I
YONEZAWA, Y
CHEMISTRY LETTERS, 1994, (01) : 129 - 132
[9] SYNTHESIS OF ACETALATED PRECURSOR OF NATURAL 3-DEOXY-D-GLYCERO-D-GALACTO-NONULOSONIC ACID (KDN)
TURIK, SV
BICHEROVA, II
KORNILOV, VI
ZHDANOV, YA
DOKLADY AKADEMII NAUK SSSR, 1991, 318 (04): : 911 - 913
[10] SYNTHESIS OF ALPHA-N-GLYCOSIDES OF 3-DEOXY-D-GLYCERO-D-GALACTO-2-NONULOSONIC ACID (KDN) USING NUCLEOBASES AND THEIR PHOTOCYCLOADDITION TO 2,3-DIMETHYL-2-BUTENE
SUN, XL
HAGA, N
OGURA, H
TAKAYANAGI, H
CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (11) : 2352 - 2356

← 1 2 3 4 5 →