4-O-α-D-glucopyranosyl-N-acetyl-D-glucosamine | 30868-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-α-D-glucopyranosyl-N-acetyl-D-glucosamine
• 英文别名: O-α-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-D-glucopyranose；α-D-glucopyranosyl-(1->4)-N-acetyl-D-glucosamine；α-D-Glcp-(1->4)-D-GlcpNAc；Glc(a1-4)GlcNAc；N-[(3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 30868-22-5
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: KFEUJDWYNGMDBV-UIPDFZSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  198
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 在 N,N-二甲基乙酰胺 、 silver trifluoromethanesulfonate 、 三乙胺 、 对硝基苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 4-O-α-D-glucopyranosyl-N-acetyl-D-glucosamine
  参考文献：
  名称：

  通过使用4-硝基苯磺酰氯，三氟甲磺酸银，N，N-二甲基乙酰胺和三乙胺的混合物进行立体选择性α-葡萄糖基化

  摘要：

  摘要在4-硝基苯磺酰氯，三氟甲磺酸银， N，N-二甲基乙酰胺和三乙胺得到O-α-d-吡喃葡萄糖基-（1→4）-和1（1→6）-2-乙酰氨基-2-脱氧-d-吡喃葡萄糖（N-乙酰基麦芽糖胺和N-乙酰基异麦芽糖胺）。描述了O-α-d-吡喃葡萄糖基-（1→4）-O- [α-d-吡喃葡萄糖基-（1→6）]-d-吡喃葡萄糖的分步合成。

  DOI：

  10.1016/0008-6215(84)85271-4

文献信息

• The acceptor specificity of amylomaltase from Escherichia coli IFO 3806.
  作者：Sumio KITAHATA、Hiromi MURAKAMI、Yoshiaki SONE、Akira MISAKI

  DOI：10.1271/bbb1961.53.2661

  日期：——

  The acceptor specificity of amylomaltase from Eschenchia coli IFO 3806 was investigated using various sugars and sugar alcohols. D-Mannose, D-glucosamine, N-acetyl-D-glucosamine, D-xylose, D-allose, isomaltose, and cellobiose were efficient acceptors in the transglycosylation reaction of this enzyme. It was shown by chemical and enzymic methods that this enzyme could transfer glycosyl residues only to the C4-hydroxyl groups of D-mannose, N-acetyl-D-glucosamine, D-allose, and D-xylose, producing oligosaccharides terminated by 4-O-α-D-glucopyranosyl-D-mannose, 4-O-α-D-glucopyranosyl-N-acetyl-D-glucosamine, 4-O-α-D-glucopyranosyl-D-allose, and 4-O-α-D-glucopyranosyl-D-xylose at the reducing ends, respectively.

  使用各种糖和糖醇研究了大肠埃希氏菌 IFO 3806 淀粉麦芽糖酶的接受特异性。在该酶的转糖基化反应中，D-甘露糖、D-葡萄糖胺、N-乙酰-D-葡萄糖胺、D-木糖、D-阿洛糖、异麦芽糖和纤维生物糖是有效的接受体。化学和酶法研究表明，这种酶只能将糖基残基转移到 D-甘露糖、N-乙酰-D-葡糖胺、D-阿洛糖和 D-木糖的 C4-羟基上、产生的寡糖在还原端分别以 4-O-α-D-吡喃葡萄糖基-D-甘露糖、4-O-α-D-吡喃葡萄糖基-N-乙酰-D-葡糖胺、4-O-α-D-吡喃葡萄糖基-D-阿洛糖和 4-O-α-D-吡喃葡萄糖基-D-木糖终止。
• Efficient one-pot enzymatic synthesis of α-(1→4)-glucosidic disaccharides through a coupled reaction catalysed by Lactobacillus acidophilus NCFM maltose phosphorylase
  作者：Hiroyuki Nakai、Adiphol Dilokpimol、Maher Abou Hachem、Birte Svensson

  DOI：10.1016/j.carres.2010.03.021

  日期：2010.5

  Lactobacillus acidophilus NCFM maltose phosphorylase (LaMalP) of glycoside hydrolase family 65 catalysed enzymatic synthesis of alpha-(1 -> 4)-glucostdic disacchandes from maltose and five monosacchandes in a coupled phosphorolysis/reverse phosphorolysis one-pot reaction Thus phosphorolysis of maltose to 0-glucose I -phosphate circumvented addition of costly 0-glucose 1-phosphate for reverse phosphorolysis with different monosacchande acceptors, resulting in 91%, 89%, 88%, 86% and 84% yield of alpha-a-glucopyranosyl-(1 4)-N-acetyl-a-glucosain inopyranose IN-acetyl-maltosamine I, alpha-b-glucopyranosyl( 1 -> 4)-o-glucosaminopyranose I maltosaminej, a-a-glucopyranosyl-(1 -> 4)-b-mannopyranose, alpha-n-glucopyranosyl-(1 -> 4)-t-fucopyranose and alpha-b-glucopyranosyl-(1 -> 4)-D-xylopyranose, respectively, from 0 1 M maltose, 0.5 M N-acetyl glucosamine, 0.1 M glucosamine. 0.1 M mannose, 1 M t-fucose and 0.5 M xylose in 02 M phosphate-citrate p1-I 62 These current yields of 0.27-0.34 g of disaccharide products from 10 mL reaction mixtures are easy to scale up and moreover the strategy can be applied to large-scale production of other oligosacchandes from low-cost disacchandes as catalysed by phosphorylases with different substrate specificities 2010 Elsevier Ltd All rights reserved.
• Champion, Elise; Andre, Isabelle; Moulis, Claire, Journal of the American Chemical Society, 2009, vol. 131, p. 7379 - 7389
  作者：Champion, Elise、Andre, Isabelle、Moulis, Claire、Boutet, Julien、Descroix, Karine、et al.

  DOI：——

  日期：——
• A stereoselective α-glucosylation by use of a mixture of 4-nitrobenzenesulfonyl chloride, silver tri-fluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine
  作者：Shinkiti Koto、Naohiko Morishima、Miho Owa、Shonosuke Zen

  DOI：10.1016/0008-6215(84)85271-4

  日期：1984.7

  Abstract Stereoselective α-glucosylation of partially protected carbohydrates with 2,3,4,6-tetra-O-benzyl-α- d -glucopyranose in dichloromethane, in the presence of a quaternary mixture of 4-nitrobenzenesulfonyl chloride, silver tri-fluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine gave O-α- d -glucopyranosyl-(1→4)- and 1(1→6)-2-acetamido-2-deoxy- d -glucopyranose (N-acetylmaltosamine

  摘要在4-硝基苯磺酰氯，三氟甲磺酸银， N，N-二甲基乙酰胺和三乙胺得到O-α-d-吡喃葡萄糖基-（1→4）-和1（1→6）-2-乙酰氨基-2-脱氧-d-吡喃葡萄糖（N-乙酰基麦芽糖胺和N-乙酰基异麦芽糖胺）。描述了O-α-d-吡喃葡萄糖基-（1→4）-O- [α-d-吡喃葡萄糖基-（1→6）]-d-吡喃葡萄糖的分步合成。