2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-2-deoxy-α-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-2-deoxy-α-D-glucopyranose
• 英文别名: 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-2-deoxy-α-D-glucose；N-acetyl-beta-D-glucosaminyl-(1->4)-alpha-D-glucosamine；N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₁₄H₂₆N₂O₁₀
• 分子量: 382.368
• InChiKey: BXVPZDGOKHWNAM-SGZQVOMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 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：
  204
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  tert-butyldimethylsilyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-2-deoxy-β-D-glucopyranoside 在 溶剂黄146 、 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-2-deoxy-β-D-glucopyranose 、 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  Towards a modular synthesis of well-defined chitooligosaccharides: synthesis of the four chitodisaccharides

  摘要：

  The total chemical synthesis of the four well-defined chitodisaccharides is described using N-trichloroacetyl (TCA) and N-benzyloxycarbonyl (Z) as C-2 protecting groups for acetamido and free amino groups, respectively. The synthesis is carried out according to a strategy that paves way to the elaboration of various homo- and hetero-chitooligosaccharides, with perfect control of the number and the position of GIcN and GIcNAc units along the oligomer chain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.010

文献信息

• Reverse hydrolysis reaction of chitin deacetylase and enzymatic synthesis of β-d-GlcNAc-(1→4)-GlcN from chitobiose
  作者：Ken Tokuyasu、Hiroshi Ono、Kiyoshi Hayashi、Yutaka Mori

  DOI：10.1016/s0008-6215(99)00213-x

  日期：1999.11

  We found that a chitin deacetylase from Colletotrichum lindemuthianum could acetylate free amino sugar residues into N-acetylated forms in the presence of 3.0 M sodium acetate. The result was analyzed using a beta-N-acetyl-hexosaminidase-coupled assay system with p-nitrophenyl beta-amino-2-deoxy-beta-D-glucopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside as the substrate, and the liberation of p-nitrophenol was observed as a consequence of enzymatic N-acetylation of the glucosamine residue at the nonreducing end of the substrate. The chitin deacetylase also acetylated chitobiose and chitotetraose as substrates, which was evidenced by the decrease in the amount of free amino sugar residues in the chitooligosaccharides. The reaction product of chitobiose after the acetylation reaction was exclusively 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1 --> 4)-2-amino-2-deoxy-D-glucose [GlcNAcGlcN], the structure of which was determined by FABMS and NMR analyses. This study offers a novel method for enzymatic N-acetylation of amino sugars, and especially with chitobiose as substrate, a selectively N-acetylated product, GlcNAcGlcN, can be synthesized. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Towards a modular synthesis of well-defined chitooligosaccharides: synthesis of the four chitodisaccharides
  作者：Nadine Barroca-Aubry、Astrid Pernet-Poil-Chevrier、Alain Domard、Stéphane Trombotto

  DOI：10.1016/j.carres.2010.05.010

  日期：2010.8

  The total chemical synthesis of the four well-defined chitodisaccharides is described using N-trichloroacetyl (TCA) and N-benzyloxycarbonyl (Z) as C-2 protecting groups for acetamido and free amino groups, respectively. The synthesis is carried out according to a strategy that paves way to the elaboration of various homo- and hetero-chitooligosaccharides, with perfect control of the number and the position of GIcN and GIcNAc units along the oligomer chain. (C) 2010 Elsevier Ltd. All rights reserved.