2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-D-glucitol | 62397-86-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-D-glucitol
• 英文别名: 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-D-glucitol；N-[(2S,3R,4S,5R)-1,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-yl]acetamide
• CAS: 62397-86-8
• 化学式: C₁₄H₂₇NO₁₁
• 分子量: 385.368
• InChiKey: JSEOLIDYPOGBEH-ZBELOFFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  209
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-D-glucitol 在 lead(IV) acetate 、 硫酸 、 碳酸氢钠 、 肼 作用下， 以 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 26.0h， 生成 D-吡喃葡萄糖
  参考文献：
  名称：

  从寡糖的还原端顺序除去单糖。I.肼和与羰基相邻的碳原子上具有糖苷取代基的糖之间的反应

  摘要：

  当糖基部分位于与醛或酮基相邻的碳原子上时，肼与具有糖苷取代基的糖平稳地反应，导致糖苷键的断裂。在过量的肼中，释放的糖苷形成a，可以以高收率从中回收还原糖。

  DOI：

  10.1016/s0040-4039(00)75790-x
• 作为产物：
  描述：

  N-乙酰-D-乳糖胺 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 6.0h， 生成 2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-D-glucitol
  参考文献：
  名称：

  NMR assignments for glucosylated and galactosylated N-acetylhexosaminitols: oligosaccharide alditols related to O-linked glycans from the protozoan parasite Trypanosoma cruzi

  摘要：

  We report full H-1 and C-13 NMR assignments for 13 gluco- or galacto-pyranosylated derivatives of GlcNAc-ol, GalNAc-ol or ManNAc-ol, many of which have been prepared by enzymatic methods. These spectra are reference data to aid the structural analysis by NMR spectroscopy of glycosylated alditols derived from the mucin of the protozoan parasite Trypanosoma cruzi. A series of structural reporter groups for the derivatives from this unusual series of O-glycans are described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00107-5

文献信息

• Sequential Removal of Monosaccharides from the Reducing End of Oligosaccharides. 2. Fundamental Studies of a Reaction between Hydrazino Compounds and Sugars Having a Glycosyl Moiety on a Carbon Atom Adjacent to a Carbonyl Group
  作者：Brad Bendiak、Mary E. Salyan、Mario Pantoja

  DOI：10.1021/jo00130a026

  日期：1995.12

  Hydrazine and certain hydrazino derivatives react with sugars having a glycosidic substituent, where the glycosyl moiety is located on a carbon atom adjacent to an aldehyde or keto group of the aglycon, resulting in cleavage of the glycosidic linkage. The reaction proceeds whether the glycon is of the alpha or beta configuration. The released glycosyl moiety, in the presence of excess hydrazino compound, reacts further to give a hydrazone derivative. Removal of the hydrazone group gives the reducing sugar derived from the glycon.
• SEQUENTIAL REMOVAL OF MONOSACCHARIDES FROM THE REDUCING END OF OLIGOSACCHARIDES AND USES THEREOF
  申请人：The Biomembrane Institute

  公开号：EP0649427B1

  公开（公告）日：1998-01-28
• US5403927A
  申请人：——

  公开号：US5403927A

  公开（公告）日：1995-04-04
• Sequential removal of monosaccharides from the reducing end of oligosaccharides. I. A reaction between hydrazine and sugars having a glycosidic substituent on a carbon atom adjacent to the carbonyl group
  作者：Brad Bendiak、Mary Ellen Salyan、Mario Pantoja

  DOI：10.1016/s0040-4039(00)75790-x

  日期：1994.1

  Hydrazine reacts smoothly with sugars having a glycosidic substituent when the glycosyl moiety is located on a carbon atom adjacent to an aldehyde or keto group, resulting in cleavage of the glycosidic linkage. In excess hydrazine, the released glycoside forms a hydrazone from which the reducing sugar may be recovered in high yields.

  当糖基部分位于与醛或酮基相邻的碳原子上时，肼与具有糖苷取代基的糖平稳地反应，导致糖苷键的断裂。在过量的肼中，释放的糖苷形成a，可以以高收率从中回收还原糖。
• NMR assignments for glucosylated and galactosylated N-acetylhexosaminitols: oligosaccharide alditols related to O-linked glycans from the protozoan parasite Trypanosoma cruzi
  作者：Christopher Jones、José O. Previato、L. Mendonça-Previato

  DOI：10.1016/s0008-6215(00)00107-5

  日期：2000.9

  We report full H-1 and C-13 NMR assignments for 13 gluco- or galacto-pyranosylated derivatives of GlcNAc-ol, GalNAc-ol or ManNAc-ol, many of which have been prepared by enzymatic methods. These spectra are reference data to aid the structural analysis by NMR spectroscopy of glycosylated alditols derived from the mucin of the protozoan parasite Trypanosoma cruzi. A series of structural reporter groups for the derivatives from this unusual series of O-glycans are described. (C) 2000 Elsevier Science Ltd. All rights reserved.