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以甲基-2,3,4,6-四-O-(4-甲氧基苄基)-1-硫代-β-D-吡喃半乳糖苷作为高效糖基供体合成含有α-Gal→β-Gal→GlcNAc序列的α-D-吡喃半乳糖基连接的寡糖。

Synthesis of alpha-D-galactopyranosyl-linked oligosaccharides containing the alpha-Gal-->beta-Gal-->GlcNAc sequence employing methyl-2,3,4,6-tetra-O-(4-methoxybenzyl)-1-thio-beta-D-galactopyranosid e as an efficient glycosyl donor.

作者信息

Reddy G V, Jain R K, Bhatti B S, Matta K L

机构信息

Department of Gynecologic Oncology, Roswell Park Cancer Institute, Buffalo, NY 14263.

出版信息

Carbohydr Res. 1994 Oct 3;263(1):67-77. doi: 10.1016/0008-6215(94)00153-7.

DOI:10.1016/0008-6215(94)00153-7
PMID:7982231
Abstract

Synthesis of two trisaccharides and a tetrasaccharide, namely, alpha-Gal-(1-->3)-beta-Gal-(1-->3)-GlcNAc-beta-OBn (6), alpha-Gal-(1-->3)-beta-Gal-(1-->4)-GlcNAc-beta-OBn (9) and alpha-Gal-(1-->3)-beta-Gal-(1-->4)-GlcNAc-beta-(1-->6)-GalNAc- alpha-OBn (19) was accomplished through development and utilization of a key alpha-galactosyl donor, methyl 2,3,4,6-tetra-O-(4- methoxybenzyl)-1-thio-beta-D-galactopyranoside (1).

摘要

通过开发和利用关键的α-半乳糖基供体2,3,4,6-四-O-(4-甲氧基苄基)-1-硫代-β-D-吡喃半乳糖苷（1），实现了两种三糖和一种四糖的合成，即α-Gal-(1→3)-β-Gal-(1→3)-GlcNAc-β-OBn（6）、α-Gal-(1→3)-β-Gal-(1→4)-GlcNAc-β-OBn（9）和α-Gal-(1→3)-β-Gal-(1→4)-GlcNAc-β-(1→6)-GalNAc-α-OBn（19）。

相似文献

1
Synthesis of alpha-D-galactopyranosyl-linked oligosaccharides containing the alpha-Gal-->beta-Gal-->GlcNAc sequence employing methyl-2,3,4,6-tetra-O-(4-methoxybenzyl)-1-thio-beta-D-galactopyranosid e as an efficient glycosyl donor.以甲基-2,3,4,6-四-O-(4-甲氧基苄基)-1-硫代-β-D-吡喃半乳糖苷作为高效糖基供体合成含有α-Gal→β-Gal→GlcNAc序列的α-D-吡喃半乳糖基连接的寡糖。
Carbohydr Res. 1994 Oct 3;263(1):67-77. doi: 10.1016/0008-6215(94)00153-7.
2
A convergent synthesis of trisaccharides with alpha-Neu5Ac-(2 --> 3)-beta-D-gal-(1 --> 4)-beta-D-GlcNAc and alpha-Neu5Ac-(2 --> 3)-beta-D-gal-(1 --> 3)-alpha-D-GalNAc sequences.
Carbohydr Res. 2000 Sep 8;328(2):147-63. doi: 10.1016/s0008-6215(00)00080-x.
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Carbohydr Res. 1998 Sep;311(3):165-9. doi: 10.1016/s0008-6215(98)00166-9.
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Synthesis of oligosaccharides containing the X-antigenic trisaccharide (alpha-L-Fucp-(1----3)-[beta-D-Galp-(1----4)]-beta-D-GlcpNAc) at their nonreducing ends.
Carbohydr Res. 1992 Mar 16;226(1):91-100. doi: 10.1016/0008-6215(92)84057-y.
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Synthesis of disaccharide glycosyl donors suitable for introduction of the beta-D-Gal p-(1-->3)-alpha-and-beta-D-Gal pNAc groups.适用于引入β-D-半乳糖基-(1→3)-α-和β-D-半乳糖胺基的二糖糖基供体的合成。
Carbohydr Res. 1995 Jul 21;272(1):1-7. doi: 10.1016/0008-6215(95)00026-p.
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Synthesis of the Sda determinant and two analogous tetrasaccharides.Sda决定簇及两种类似四糖的合成。
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A convenient synthesis of lacto-N-biose I [beta-D-Gal p-(1-->3)-beta-D- Glc pNAc] linked oligosaccharides from phenyl O-(tetra-O-acetyl-beta-D- galactopyranosyl)-(1-->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio- beta-D- glucopyranoside.一种从苯基 O-(四-O-乙酰基-β-D-吡喃半乳糖基)-(1→3)-4,6-二-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷便捷合成乳糖-N-二糖 I [β-D-半乳糖吡喃糖基-(1→3)-β-D-葡萄糖吡喃糖胺] 连接的寡糖的方法。
Carbohydr Res. 1993 Mar 17;241:165-76. doi: 10.1016/0008-6215(93)80103-l.
8
Synthesis of Hex p-(1-->4)-beta-D-Glc pNAc-(1-->2)-alpha-D-Man p-(1-->O)(CH2)7CH3 probes for exploration of the substrate specificity of glycosyltransferases: Part I, Hex = beta-D-Gal, 4-deoxy-beta-D-Gal, 4-O-methyl-beta-D-Gal, 4-deoxy-4-fluoro-beta-D-Gal, or beta-D-Glc.用于探索糖基转移酶底物特异性的己糖对-(1→4)-β-D-葡糖胺-(1→2)-α-D-甘露糖-(1→O)(CH₂)₇CH₃探针的合成：第一部分，己糖 = β-D-半乳糖、4-脱氧-β-D-半乳糖、4-O-甲基-β-D-半乳糖、4-脱氧-4-氟-β-D-半乳糖或β-D-葡萄糖。
Carbohydr Res. 1996 Sep 23;291:63-83. doi: 10.1016/s0008-6215(96)00154-1.
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Synthetic mucin fragments. Benzyl O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-(1----3)-O-beta-D- galactopyranosyl-(1----3)-O-[(2-acetamido-2-deoxy-beta-D-glucopyran osy l)- (1----6)]-2-acetamido-2-deoxy-alpha-D-galactopyranoside and benzyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-O-beta-D- galactopyranosyl-(1----3)-O-[beta-D-galactopyranosyl-(1----6)]-2-ac eta mido- 2-deoxy-alpha-D-galactopyranoside.合成粘蛋白片段。苄基 O-(2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖基)-(1→3)-O-β-D-吡喃半乳糖基-(1→3)-O-[(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→6)]-2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖苷和苄基 O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→3)-O-β-D-吡喃半乳糖基-(1→3)-O-[β-D-吡喃半乳糖基-(1→6)]-2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖苷。
Carbohydr Res. 1988 Dec 1;183(2):163-73. doi: 10.1016/0008-6215(88)84071-0.

引用本文的文献

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Modulation of the regioselectivity of a Bacillus alpha-galactosidase by directed evolution.通过定向进化对芽孢杆菌α-半乳糖苷酶区域选择性的调控。
Glycoconj J. 2001 Mar;18(3):215-23. doi: 10.1023/a:1012448522187.
2
Synthesis of Gal-beta-(1-->4)-GlcNac-beta-(1-->6)-[Gal-beta-(1-->3]-GalNAc-alpha- OBn oligosaccharides bearing O-methyl or O-sulfo groups at C-3 of the Gal residue: specific acceptors for Gal: 3-O-sulfotransferases.在半乳糖残基的C-3位带有O-甲基或O-磺基的Gal-β-(1→4)-GlcNac-β-(1→6)-[Gal-β-(1→3)]-GalNAc-α-OBn寡糖的合成：Gal:3-O-磺基转移酶的特异性受体。
Glycoconj J. 1998 Oct;15(10):951-9. doi: 10.1023/a:1006977607394.
3
One-pot enzymatic synthesis of the Gal alpha 1-->3Gal beta 1-->4GlcNAc sequence with in situ UDP-Gal regeneration.
通过原位UDP-Gal再生实现一锅法酶促合成Galα1→3Galβ1→4GlcNAc序列
Glycoconj J. 1996 Aug;13(4):687-92. doi: 10.1007/BF00731458.