N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-seryl-alanine tert-butyl ester | 144923-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-seryl-alanine tert-butyl ester
• CAS: 144923-63-7
• 化学式: C₃₄H₄₇N₃O₁₅
• 分子量: 737.758
• InChiKey: DPJKKKXAIAZBPW-HVPBNCMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  52.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  229.42
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-seryl-alanine tert-butyl ester 在 palladium on activated charcoal 吡啶 、 四(三苯基膦)钯 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 丙二酸二甲酯 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 104.0h， 生成 N-benzyloxycarbonyl-alanyl--seryl-alanine tert-butyl ester
  参考文献：
  名称：

  Synthetic O-glycopeptides as model substrates for glycosyltransferases

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)80230-x
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide 、 Z-Ser-Ala-OtBu 在 4 A molecular sieve 、 氰化汞 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以54%的产率得到N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-seryl-alanine tert-butyl ester
  参考文献：
  名称：

  Synthetic O-glycopeptides as model substrates for glycosyltransferases

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)80230-x

文献信息

• Enzymatic glycosylation of o-glycopeptides
  作者：Michael Schultz、Horst Kunz

  DOI：10.1016/s0040-4039(00)79082-4

  日期：1992.9

  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).