Synthesis of oligosaccharides related to HNK-1 antigen, part 3 -: Synthesis of 3-O-sulfoglucuronyl lacto-N-neotetraose 2-aminoethyl glycoside and biotinylated neoglycoconjugates thereof

被引：38

作者：

Kornilov, AV ^{[1
]}

Sherman, AA ^{[1
]}

Kononov, LO ^{[1
]}

Shashkov, AS ^{[1
]}

Nifant'ev, NE ^{[1
]}

机构：

[1] ND Zelinskii Organ Chem Inst, Moscow 117913, Russia

来源：

CARBOHYDRATE RESEARCH | 2000年 / 329卷 / 04期

基金：

俄罗斯基础研究基金会;

关键词：

HNK-1; neoglycoconjugates; glucuronic acid; lactonization;

D O I：

10.1016/S0008-6215(00)00258-5

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 2-aminoethyl glycoside of pentasaccharide 3-O-sulfo-GlcA(beta -1 --> 3)Gal(beta -1 --> 4)GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta (1) and its conjugates with biotin and biotinylated polyacrylic acid were synthesized as molecular probes to investigate the recognition of the HNK-1 epitope containing carbohydrates by proteins. Key steps in the first of two investigated schemes for the preparation of the target compound 1 were (a) assembling of the pentasaccharide backbone (compound 10) by glycosylation of selectively substituted allyl glycoside of the trisaccharide GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta with glucuronyl-galactose glycosyl donor, (b) transformation of the allyl aglycon in 10 into 2-azidoethyl one (to give 11), (c) selective deprotection of the OH group at C-3 of the GlcA residue in 11 via saponification, intramolecular formation of 6,3-lacton (13) and its methanolysis, and (d) subsequent O-sulfation. The alternative scheme with the use of 2-azido-ethyl glycoside of the trisaccharide GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta instead of the allyl glycoside 6 was less effective due to smaller yield at the step of pentasaccharide synthesis. Additionally to 1 the 2-aminoethyl glycosides of the oligosaccharides GlcA(beta -1 --> 3)Gal(beta -1 --> 4)GlcNAc(beta -1 --> 3)Gal(beta -1 --> 4)Glc(beta, 3-O-sulfo-GlcA(beta -1 --> 3)Gal(beta, and GlcA(beta -1 --> 3)Gal(beta were also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：717 / 730

页数：14

共 12 条

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Kononov, LO
Kornilov, AV
Sherman, AA
Zyryanov, EV
Zatonsky, GV
Shashkov, AS
Nifant'ev, NE
BIOORGANICHESKAYA KHIMIYA, 1998, 24 (08): : 608 - 622
[2] The chemical synthesis of human milk oligosaccharides: Lacto-N-neotetraose (Galβ1 →4GlcNAcβ1 →3Galβ1 →4Glc)
Bandara, Mithila D.
Stine, Keith J.
Demchenko, Alexei, V
CARBOHYDRATE RESEARCH, 2019, 483
[3] Synthesis of β-GlcA-(1→3)-β-Gal and α-GalNAc-(1→4)-β-GlcA-(1→3)-β-Gal as biotinylated 2-aminoethyl glycoside and the streptavidin complex formation
Tamura, J
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JOURNAL OF CARBOHYDRATE CHEMISTRY, 1999, 18 (01) : 1 - 14
[4] Synthesis of oligosaccharides related to the HNK-1 antigen .1. Synthesis of selectively protected allyl 3-O-[methyl(beta-D-glucopyranosyl)uronate]-beta-D-galactopyranoside
Kornilov, AV
Kononov, LO
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Shashkov, AS
Nifantev, NE
BIOORGANICHESKAYA KHIMIYA, 1997, 23 (08): : 655 - 666
[5] Non-imidazole histamine H3 ligands: part V. synthesis and preliminary pharmacological investigation of 1-[2-thiazol-4-yl- and 1-[2-thiazol-5-yl-(2-aminoethyl)]-4-n-propylpiperazine derivatives
Roman Guryn
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Krzysztof Walczyński
Medicinal Chemistry Research, 2013, 22 : 3640 - 3652
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Guryn, Roman
Staszewski, Marek
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MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (08) : 3640 - 3652
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[9] SYNTHESIS OF LIGANDS RELATED TO THE O-SPECIFIC ANTIGEN OF TYPE-1 SHIGELLA-DYSENTERIAE .3. GLYCOSYLATION OF 4,6-O-SUBSTITUTED DERIVATIVES OF METHYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE WITH GLYCOSYL DONORS DERIVED FROM MONOSACCHARIDES AND OLIGOSACCHARIDES
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