N-benzyloxycarbonyl-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-seryl-alanine tert-butyl ester | 144923-65-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzyloxycarbonyl-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-seryl-alanine tert-butyl ester
• CAS: 144923-65-9
• 化学式: C₂₆H₃₉N₃O₁₁
• 分子量: 569.609
• InChiKey: RUZIFETWVSMNKS-SIHXKMAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.91
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  201.98
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-seryl-alanine tert-butyl ester 、 alkaline earth salt of/the/ methylsulfuric acid 在 苯磺酰胺 、 sodium azide 、 cacodylate buffer 、 manganese(ll) chloride 作用下， 反应 48.0h， 生成 (S)-2-{(S)-3-[(2R,3R,4R,5S,6R)-3-Acetylamino-4-hydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-benzyloxycarbonylamino-propionylamino}-propionic acid tert-butyl ester
  参考文献：
  名称：

  Enzymatic glycosylation of o-glycopeptides

  摘要：

  O-Glycosylation of serine derivatives carried out with N-urethane protected glucosamine yields O-glycopeptides which are regio-and stereoselectively galactosylated with the aid of beta-1,4-galactosyltransferase (EC2.4.1.22).

  DOI：

  10.1016/s0040-4039(00)79082-4
• 作为产物：
  描述：

  (S)-2-[(S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxy)-propionylamino]-propionic acid tert-butyl ester 在 吡啶 、 肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N-benzyloxycarbonyl-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-seryl-alanine tert-butyl ester
  参考文献：
  名称：

  Enzymatic glycosylation of o-glycopeptides

  摘要：

  O-Glycosylation of serine derivatives carried out with N-urethane protected glucosamine yields O-glycopeptides which are regio-and stereoselectively galactosylated with the aid of beta-1,4-galactosyltransferase (EC2.4.1.22).

  DOI：

  10.1016/s0040-4039(00)79082-4

文献信息

• Synthetic O-glycopeptides as model substrates for glycosyltransferases
  作者：Michael Schultz、Horst Kunz

  DOI：10.1016/s0957-4166(00)80230-x

  日期：1993.6

  A new approach to O-glycopeptides of the glucosamine type is described. N-Urethane protected, peracetylated glucosamine is converted into its 1-thio (1-bromo) derivative and used for glycosylation of a variety of protected serine or threonine derivatives as acceptors. The urethane group is easily exchanged for the natural N-acetyl moiety and O-deacetylation is achieved with hydrazine/methanol. The resulting O-GlcNAc derivatives are subjected to an enzymatic galactosylation procedure using beta-1,4-galactosyluwsferase (EC 2.4.1.22) to furnish O-glycopeptides of the neolactosamine type.