N-acetyl-N-(3-thio(2-aminoethyl))propyl(α-D-galactopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosylamine | 343248-11-3

• 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(α-D-galactopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosylamine
• 英文别名: N-[3-(2-aminoethylsulfanyl)propyl]-N-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]acetamide
• CAS: 343248-11-3
• 化学式: C₂₅H₄₆N₂O₁₆S
• 分子量: 662.71
• InChiKey: SHCVKYNICGIPIP-PVPAYKMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  320
• 氢给体数：
  11
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  Z-Glu-Gly 、 N-acetyl-N-(3-thio(2-aminoethyl))propyl(α-D-galactopyranosyl)-(1->3)-(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63%的产率得到[N¹-(benzyloxycarbonyl)-N⁴-[N-acetyl-N-(3-thio(2-acetamidoethyl))propyl((α-D-galactopyranosyl)-(1->3)-(β-D-galactopyranosylamine)-(1->4)-β-D-glucopyranosyl]-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-benzyl-α-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosylamine 在 氨 、 sodium 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 N-acetyl-N-(3-thio(2-aminoethyl))propyl(α-D-galactopyranosyl)-(1->3)-(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

• 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.