N-acetyl-N-(3-thio(2-aminoethyl))propyl-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosylamine | 202802-20-8

• 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-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosylamine
• 英文别名: N-[3-(2-aminoethylsulfanyl)propyl]-N-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]acetamide
• CAS: 202802-20-8
• 化学式: C₁₉H₃₆N₂O₁₁S
• 分子量: 500.568
• InChiKey: MDJOZCUAMAQBST-BAGUKLQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  241
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Z-Glu-Gly 、 N-acetyl-N-(3-thio(2-aminoethyl))propyl-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosylamine 在 谷氨酰胺转移酶 作用下， 以 phosphate buffer 为溶剂， 以89%的产率得到[N¹-(benzyloxycarbonyl)-N⁴-[N-acetyl-N-(3-thio(2-acetamidoethyl))propyl((β-D-galactopyranosyl)-(1->4)-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：

  N-acetyl-N-allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glycopyranosylamine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 N-acetyl-N-(3-thio(2-aminoethyl))propyl-(β-D-galactopyranosyl)-(1->4)-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

• Enzymatic Synthesis of Neoglycopeptide Building Blocks
  作者：Delphine Ramos、Patrick Rollin、Werner Klaffke

  DOI：10.1002/(sici)1521-3773(20000117)39:2<396::aid-anie396>3.0.co;2-a

  日期：2000.1.17
• 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.