β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-D-glucopyranose | 6050-69-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-D-glucopyranose
• 英文别名: (N-Acetyl)-glucosamin-4-β-galaktosid；N-Acetyl-Laktosamin；N-[(3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 6050-69-7
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: KFEUJDWYNGMDBV-NMVBVQPTSA-N

物化性质

• 沸点：
  805.5±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-D-glucopyranose 、 乙酸酐 在 吡啶 作用下， 以152 mg的产率得到2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Endo-β-N-acetylglucosaminidase-catalyzed polymerization of β-Glcp-(1→4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation

  摘要：

  An alternative synthesis of beta-Glcp-(1 -> 4)-GlcpNAc oxazoline is described, and its enzymatic reaction with the endo-beta-N-acetylglucosaminidase from Arthrobacter protophormiae (Endo-A) was re-investigated. Under normal transglycosylation conditions with a catalytic amount of enzyme, Enclo-A showed only marginal activity for transglycosylation with the disaccharide oxazoline, consistent with our previous observations. However, when used in a relatively large quantity, Endo-A could promote the transglycosylation of the disaccharide oxazoline to a GlcpNAc-Asn acceptor. In addition to the initial transglycosylation product, a series of large oligosaccharides were also formed due to the tandem transglycosylation to the terminal glucose residues in the intermediate products. In the absence of an external acceptor, Enclo-A could polymerize the disaccharide oxazoline to form oligo- and polysaccharides having the -4-beta-(Glcp-(1 -> 4)-beta-GlcpNAc)-1-repeating units. This is the first example of an endo-beta-N-acetylglucosaminidase-promoted polymerization of activated oligosaccharide substrates. This enzymatic polymerization may find useful applications for the synthesis of novel artificial polysaccharides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.01.016
• 作为产物：
  描述：

  在 palladium hydroxide on carbon 、 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  Endo-β-N-acetylglucosaminidase-catalyzed polymerization of β-Glcp-(1→4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation

  摘要：

  An alternative synthesis of beta-Glcp-(1 -> 4)-GlcpNAc oxazoline is described, and its enzymatic reaction with the endo-beta-N-acetylglucosaminidase from Arthrobacter protophormiae (Endo-A) was re-investigated. Under normal transglycosylation conditions with a catalytic amount of enzyme, Enclo-A showed only marginal activity for transglycosylation with the disaccharide oxazoline, consistent with our previous observations. However, when used in a relatively large quantity, Endo-A could promote the transglycosylation of the disaccharide oxazoline to a GlcpNAc-Asn acceptor. In addition to the initial transglycosylation product, a series of large oligosaccharides were also formed due to the tandem transglycosylation to the terminal glucose residues in the intermediate products. In the absence of an external acceptor, Enclo-A could polymerize the disaccharide oxazoline to form oligo- and polysaccharides having the -4-beta-(Glcp-(1 -> 4)-beta-GlcpNAc)-1-repeating units. This is the first example of an endo-beta-N-acetylglucosaminidase-promoted polymerization of activated oligosaccharide substrates. This enzymatic polymerization may find useful applications for the synthesis of novel artificial polysaccharides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.01.016

文献信息

• Linear synthesis of the branched pentasaccharide repeats of O-antigens from Shigella flexneri 1a and 1b demonstrating the major steric hindrance associated with type-specific glucosylation
  作者：Jason M. Hargreaves、Yann Le Guen、Catherine Guerreiro、Karine Descroix、Laurence A. Mulard

  DOI：10.1039/c4ob01200c

  日期：——

  Shigella flexneri serotypes 1b and 1a are Gram-negative enteroinvasive bacteria causing shigellosis in humans. The O-antigen from S. flexneri 1b is a →2)-[3Ac/4Ac]-α-L-Rhap-(1→2)-α-L-Rhap-(1→3)-[2Ac]-α-L-Rhap-(1→3)-[α-D-Glcp-(1→4)]-β-D-GlcpNAc-(1→}n branched polysaccharide (AcABAcC(E)D}n). It is identical to that from S. flexneri 1a, except for the 2C-acetate. A concise synthesis of the disaccharide

  弗氏志贺氏菌血清型1b和1a是革兰氏阴性肠内侵染细菌，可导致人类志贺氏菌病。O-抗原从福氏1b是→2） - [3AC / 4AC]-α-大号-RHA p - （1→2）-α-大号-RHA p - （1→3） - [2AC ] -α - L -Rha p-（1→3）-[α- D -Glc p-（1→4）]-β- D -Glc p NAc-（1→} n支链多糖（ Ac AB Ac C（E）D} n）。它与弗氏链球菌1a的相同，除了2 C-乙酸。二糖ED，三糖Ac C（E）D和C（E）D，四糖B Ac C（E）D和BC（E）D以及五糖AB Ac C（E）D和ABC（E）的简明合成描述了从2- N-乙酰基-D-氨基葡萄糖苷受体开始并使用亚氨酸酯糖基化化学反应的D）D 。通过有效的立体选择性[E + D]偶联有效地引入了E残基。相反，高产的[C + ED]糖基化需要苛刻的条件和适当的供体调节。不论残基C的空间大小如何，O-3
• β-Glucosylation of chitooligomers by galactosyltransferase
  作者：Vladimír Křen、Jana Dvořáková、Ulrike Gambert、Petr Sedmera、Vladimír Havlíček、Joachim Thiem、Karel Bezouška

  DOI：10.1016/s0008-6215(97)00248-6

  日期：1997.12

  Galactosyltransferase from bovine milk was found to be able to utilise UDP-Glc to transfer Glc onto GlcNAc and chitooligomers [-beta-GlcNAc-(1-->4)-](n), n=2-4. beta-Glucosylated products were used in binding studies with NKR-P1A protein cloned from rat natural killer cells. (C) 1998 Elsevier Science Ltd.
• Endo-β-N-acetylglucosaminidase-catalyzed polymerization of β-Glcp-(1→4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation
  作者：Hirofumi Ochiai、Wei Huang、Lai-Xi Wang

  DOI：10.1016/j.carres.2009.01.016

  日期：2009.3

  An alternative synthesis of beta-Glcp-(1 -> 4)-GlcpNAc oxazoline is described, and its enzymatic reaction with the endo-beta-N-acetylglucosaminidase from Arthrobacter protophormiae (Endo-A) was re-investigated. Under normal transglycosylation conditions with a catalytic amount of enzyme, Enclo-A showed only marginal activity for transglycosylation with the disaccharide oxazoline, consistent with our previous observations. However, when used in a relatively large quantity, Endo-A could promote the transglycosylation of the disaccharide oxazoline to a GlcpNAc-Asn acceptor. In addition to the initial transglycosylation product, a series of large oligosaccharides were also formed due to the tandem transglycosylation to the terminal glucose residues in the intermediate products. In the absence of an external acceptor, Enclo-A could polymerize the disaccharide oxazoline to form oligo- and polysaccharides having the -4-beta-(Glcp-(1 -> 4)-beta-GlcpNAc)-1-repeating units. This is the first example of an endo-beta-N-acetylglucosaminidase-promoted polymerization of activated oligosaccharide substrates. This enzymatic polymerization may find useful applications for the synthesis of novel artificial polysaccharides. (C) 2009 Elsevier Ltd. All rights reserved.