(S)-2-Amino-pentanedioic acid 5-amide 1-{[(1S,2R)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanylsulfanylmethyl)-propyl]-amide} | 870196-25-1

• 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: (S)-2-Amino-pentanedioic acid 5-amide 1-{[(1S,2R)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanylsulfanylmethyl)-propyl]-amide}
• CAS: 870196-25-1
• 化学式: C₄₁H₅₅N₃O₃SSi₂
• 分子量: 726.143
• InChiKey: USVPMCLCBWANFL-XLKDAERCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  50.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  107.44
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-pentanedioic acid 5-amide 1-{[(1S,2R)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanylsulfanylmethyl)-propyl]-amide} 在 四丁基氟化铵 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 ((S)-2-{(S)-2-[(S)-3-Carbamoyl-1-((1S,2R)-2-hydroxy-1-mercaptomethyl-propylcarbamoyl)-propylcarbamoyl]-pyrrolidin-1-yl}-1-carbamoylmethyl-2-oxo-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of (2R,3S) 3-amino-4-mercapto-2-butanol, a threonine analogue for covalent inhibition of sortases

  摘要：

  L-Threonine 2 was converted in seven steps into the protected aminomercaptoalcohol 8, a threonine mimic. This compound 8 was coupled to various oligopeptides to produce two different tetrapeptide analogues, for example, 11 and 17, which were shown to inhibit the Sortase enzymes (SrtA and SrtB) via covalent attachment of the thiol groups of 11 and 17 to the catalytically active cysteine residue of the Sortase enzymes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.073
• 作为产物：
  描述：

  [(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanylsulfanylmethyl)-propyl]-carbamic acid tert-butyl ester 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 18.83h， 生成 (S)-2-Amino-pentanedioic acid 5-amide 1-{[(1S,2R)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanylsulfanylmethyl)-propyl]-amide}
  参考文献：
  名称：

  Synthesis of (2R,3S) 3-amino-4-mercapto-2-butanol, a threonine analogue for covalent inhibition of sortases

  摘要：

  L-Threonine 2 was converted in seven steps into the protected aminomercaptoalcohol 8, a threonine mimic. This compound 8 was coupled to various oligopeptides to produce two different tetrapeptide analogues, for example, 11 and 17, which were shown to inhibit the Sortase enzymes (SrtA and SrtB) via covalent attachment of the thiol groups of 11 and 17 to the catalytically active cysteine residue of the Sortase enzymes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.073