N-acetyl-N-(3-thio-(2-aminoethyl))propyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine | 343248-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetyl-N-(3-thio-(2-aminoethyl))propyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-[acetyl-[3-(2-aminoethylsulfanyl)propyl]amino]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 343248-09-9
• 化学式: C₁₅H₂₉N₃O₆S
• 分子量: 379.478
• InChiKey: BCNDDRWJPPDUOK-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  171
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Z-Glu-Gly 、 N-acetyl-N-(3-thio-(2-aminoethyl))propyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine 在 谷氨酰胺转移酶 作用下， 以 phosphate buffer 为溶剂， 生成 [N¹-(benzyloxycarbonyl)-N⁴-[N-acetyl-N-(3-thio(2-acetamidoethyl))propyl(2-acetamido-2-deoxy-β-D-glucopyranosylamine)]-L-glutamyl]-L-glycine
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Neoglycopeptides:  Application to an α-Gal-Terminated Neoglycopeptide

  摘要：

  A novel methodology; for the enzymatic preparation from suitably derivatized oligosaccharides of N-linked neoglycopeptides using the microbial glutaminyl-peptide gamma -glutamyl transferase, transglutaminase (TGase), is described, N-Allyl glycosides of various oligosaccharides were photochemically coupled with cysteamine to yield amino-terminated thioether spacers, which were accepted by transglutaminase to transamidate the side-chain gamma -carboxamide group in the dipeptide Z-Gln-Gly.

  DOI：

  10.1021/jo001439c
• 作为产物：
  描述：

  D-GlcNAc 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 105.0h， 生成 N-acetyl-N-(3-thio-(2-aminoethyl))propyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Neoglycopeptides:  Application to an α-Gal-Terminated Neoglycopeptide

  摘要：

  A novel methodology; for the enzymatic preparation from suitably derivatized oligosaccharides of N-linked neoglycopeptides using the microbial glutaminyl-peptide gamma -glutamyl transferase, transglutaminase (TGase), is described, N-Allyl glycosides of various oligosaccharides were photochemically coupled with cysteamine to yield amino-terminated thioether spacers, which were accepted by transglutaminase to transamidate the side-chain gamma -carboxamide group in the dipeptide Z-Gln-Gly.

  DOI：

  10.1021/jo001439c

文献信息

• Chemoenzymatic Synthesis of Neoglycopeptides:  Application to an α-Gal-Terminated Neoglycopeptide
  作者：Delphine Ramos、Patrick Rollin、Werner Klaffke

  DOI：10.1021/jo001439c

  日期：2001.5.1

  A novel methodology; for the enzymatic preparation from suitably derivatized oligosaccharides of N-linked neoglycopeptides using the microbial glutaminyl-peptide gamma -glutamyl transferase, transglutaminase (TGase), is described, N-Allyl glycosides of various oligosaccharides were photochemically coupled with cysteamine to yield amino-terminated thioether spacers, which were accepted by transglutaminase to transamidate the side-chain gamma -carboxamide group in the dipeptide Z-Gln-Gly.