N-[(2R,3R,4R,5R)-3,4,5-三羟基-1-氧代-6-[(2R,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基己烷-2-基]乙酰胺 | 72142-81-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: N-[(2R,3R,4R,5R)-3,4,5-三羟基-1-氧代-6-[(2R,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基己烷-2-基]乙酰胺
• 英文名称: 6-O-Galactopyranosyl-2-acetamido-2-deoxygalactose
• 英文别名: N-[(2R,3R,4R,5R)-3,4,5-trihydroxy-1-oxo-6-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-yl]acetamide
• CAS: 72142-81-5
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: FGYNENQLWILFLQ-WXOWSPKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  206
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-[(2R,3R,4R,5R)-3,4,5-三羟基-1-氧代-6-[(2R,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基己烷-2-基]乙酰胺 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 生成
  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
• 作为产物：
  描述：

  N-乙酰-D-半乳糖胺 、 4-硝基苯基-D-吡喃葡糖苷 在 β-galactosidase 磷酸三乙酯 、 sodium acetate 作用下， 以 水 为溶剂， 生成 N-[(2R,3R,4R,5R)-3,4,5-三羟基-1-氧代-6-[(2R,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基己烷-2-基]乙酰胺 、 2-acetylamino-O⁴-β-D-galactopyranosyl-2-deoxy-D-galactose
  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

• Regioselectivity in β-Galactosidase-catalyzed Transglycosylation for the Enzymatic Assembly of<scp>D</scp>-Galactosyl-<scp>D</scp>-mannose
  作者：Mariko MIYASATO、Katsumi AJISAKA

  DOI：10.1271/bbb.68.2086

  日期：2004.1

  different origins. The relative hydrolysis rate of Gal beta-pNP and D-galactosyl-D-mannoses, of various linkages, was also measured in the presence of beta-1,3-galactosidase and was found to correlate well with the ratio of disaccharides formed by transglycosylation. The unexpected regioselectivity using D-mannose can therefore be explained by an anomalous specificity in the hydrolysis reaction. By utilizing

  研究了以D-甘露糖为受体的环半芽孢杆菌ATCC 31382（β-1,3-半乳糖苷酶）衍生的β-半乳糖苷酶在反半乳糖基化反应中的区域选择性。发现该D-甘露糖相关的区域选择性不同于使用GlcNAc或GalNAc作为受体的反应，不仅对于β-1,3-半乳糖苷酶而且对于不同来源的β-半乳糖苷酶。在存在β-1,3-半乳糖苷酶的情况下，还测量了具有各种键的Galβ-pNP和D-半乳糖基-D-甘露糖的相对水解速率，发现其与通过转糖基化形成的二糖的比例具有很好的相关性。 。因此，可以通过水解反应中的异常特异性来解释使用D-甘露糖的意外的区域选择性。
• Synthesis of 2-acetamido-2-deoxy-3-O-β-d-galactopyrano-syl-d-galactose by the sequential use of β-d-galactosidases from bovine testes and escherichia coli
  作者：Lars Hedbys、Elisabet Johansson、Klaus Mosbach、Per-Olof Larsson、Alf Gunnarsson、Sigfrid Svensson

  DOI：10.1016/0008-6215(89)84036-4

  日期：1989.3

  beta-D-Galp-(1----3)-D-GalNAc (1) was synthesised from lactose and GalNAc on a mmolar scale by transgalactosylation using beta-D-galactosidase from bovine testes. The large proportions of unwanted oligosaccharides in the product mixture were removed by treatment with beta-D-galactosidase from E. coli, which left 1, monosaccharides, and a small proportion of trisaccharides. Carbon-Celite chromatography

  使用来自牛睾丸的β-D-半乳糖苷酶经半乳糖基化反应，由乳糖和GalNAc以毫摩尔级合成β-D-Galp-（1 ---- 3）-D-GalNAc（1）。通过用来自大肠杆菌的β-D-半乳糖苷酶处理除去产物混合物中的大部分不需要的寡糖，这留下了1个单糖和一小部分的三糖。然后，基于添加的GalNAc，碳-硅藻土色谱法得到1，产率为21％。