β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-((2R,3S,4R,5R,6R)-5-Acetylamino-4,6-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-4-hydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide；Galbeta1-4GlcNAcbeta1-4GlcNAcbeta；N-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₂₂H₃₈N₂O₁₆
• 分子量: 586.548
• InChiKey: OCPQLCXSCTTXMX-NDHNAMKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  286
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose 在 recombinant Escherichia coli K-12 galactokinase 、 recombinant Bifidobacterium longum UDP-sugar pyrophosphorylase 、 recombinant Neisseria meningitides β1,4-galactosyltransferase 、 recombinant fusion enzyme of Bifidobacterium longum N-acetylhexosamine-1-kinase and Escheerichiacoli N-acetylglucosamine uridylyltransferase 、 recombinant Helicobacter pylori β1,3-N-acetylgluco-saminyltransferase 、 尿苷-5'-三磷酸 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 28.0h， 生成 β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  唾液酸乳糖胺接枝壳寡糖的酶法合成

  摘要：

  开发了一种有效的酶组装策略，用于简明合成结构明确的唾液酸化壳寡糖。β-1,3- N-乙酰基-葡糖胺化和 β-1,4-半乳糖基化的两个酶模块用于将N-乙酰乳糖胺 (LacNAc) 单元接枝到壳寡糖上。LacNAc 接枝壳寡糖通过两个酶促唾液酸化模块用 α-2,3- 或 α-2,6- 唾液酸化进一步修饰，生成总共 20 种唾液酸化壳寡糖。用合成的唾液酸化壳寡糖对流感病毒诱导的细胞病变进行的抑制研究表明，唾液酸键和链长都有助于结合偏好和抑制效力。

  DOI：

  10.1002/cjoc.202300004
• 作为产物：
  描述：

  、 4-甲基香豆素-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷 在 Bacillus sp. chitinase 100 kDa 作用下， 反应 16.67h， 生成 β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Chemoenzymatic synthesis of N-linked neoglycoproteins through a chitinase-catalyzed transglycosylation

  摘要：

  A novel application of the Bacillus sp. chitinase for the chemoenzymatic synthesis of N-linked neoglycoproteins is described. Three chitinases with different molecular size were purified from the crude chitinase preparation. The purified chitinases were evaluated for their hydrolytic and transglycosylation activity. One chitinase with a molecular size of 100 kDa (Chi100) was identified to be the one with highest transglycosylation/ hydrolysis ratio. Chi100 could effectively recognize LacNAc-oxazoline and Man alpha 1,3Glc beta 1,4GlcNAc-oxazoline as the donor substrate to glycosylate Asn-linked GlcNAc, while it was unable to recognize Man beta 1,4GlcNAc and Man(3)GlcNAc-oxazolines as the donor substrates. The chitinase-catalyzed transglycosylation was successfully extended to the remodeling of ribonuclease B to afford neoglycoproteins. Although the yield needs to be optimized, the chitinase-catalyzed transglycosylation provides a potentially useful tool for the synthesis of neoglycoproteins carrying novel N-linked oligosaccharides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.042

文献信息

• Label-Free, Real-Time Glycosyltransferase Assay Based on a Fluorescent Artificial Chemosensor
  作者：Jirarut Wongkongkatep、Yoshifumi Miyahara、Akio Ojida、Itaru Hamachi

  DOI：10.1002/anie.200503107

  日期：2006.1.16
• Chemoenzymatic synthesis of N-linked neoglycoproteins through a chitinase-catalyzed transglycosylation
  作者：Cishan Li、Wei Huang、Lai-Xi Wang

  DOI：10.1016/j.bmc.2008.08.042

  日期：2008.9

  A novel application of the Bacillus sp. chitinase for the chemoenzymatic synthesis of N-linked neoglycoproteins is described. Three chitinases with different molecular size were purified from the crude chitinase preparation. The purified chitinases were evaluated for their hydrolytic and transglycosylation activity. One chitinase with a molecular size of 100 kDa (Chi100) was identified to be the one with highest transglycosylation/ hydrolysis ratio. Chi100 could effectively recognize LacNAc-oxazoline and Man alpha 1,3Glc beta 1,4GlcNAc-oxazoline as the donor substrate to glycosylate Asn-linked GlcNAc, while it was unable to recognize Man beta 1,4GlcNAc and Man(3)GlcNAc-oxazolines as the donor substrates. The chitinase-catalyzed transglycosylation was successfully extended to the remodeling of ribonuclease B to afford neoglycoproteins. Although the yield needs to be optimized, the chitinase-catalyzed transglycosylation provides a potentially useful tool for the synthesis of neoglycoproteins carrying novel N-linked oligosaccharides. (C) 2008 Elsevier Ltd. All rights reserved.
• Enzymatic Synthesis of Sialyl Lactosamine Grafted Chitooligosaccharides
  作者：Jun Yan、Jianghua Li、Zhifei Hu、Xiaoyao Ma、Yun Li、Xihuan Hu、Jinfeng Ye、Wei Wang、Renzhong Wan、Hongzhi Cao

  DOI：10.1002/cjoc.202300004

  日期：——

  An efficient enzymatic assembly strategy was developed for the concise synthesis of structurally well-defined sialylated chitooligosaccharides. Two enzyme modules for the β-1,3-N-acetyl-glucosaminylation and β-1,4-galactosylation were applied for the grafting N-acetyl lactosamine (LacNAc) unit(s) onto the chitooligosaccharides. The LacNAc grafted chitooligosaccharides were further modified with α-2

  开发了一种有效的酶组装策略，用于简明合成结构明确的唾液酸化壳寡糖。β-1,3- N-乙酰基-葡糖胺化和 β-1,4-半乳糖基化的两个酶模块用于将N-乙酰乳糖胺 (LacNAc) 单元接枝到壳寡糖上。LacNAc 接枝壳寡糖通过两个酶促唾液酸化模块用 α-2,3- 或 α-2,6- 唾液酸化进一步修饰，生成总共 20 种唾液酸化壳寡糖。用合成的唾液酸化壳寡糖对流感病毒诱导的细胞病变进行的抑制研究表明，唾液酸键和链长都有助于结合偏好和抑制效力。