(S)-2-{(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-3-hydroxy-propionylamino}-3-hydroxy-propionic acid | 195261-00-8

• 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-{(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-3-hydroxy-propionylamino}-3-hydroxy-propionic acid
• 英文别名: N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-L-seryl-L-seryl-L-serine；(2S)-2-[[(2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoic acid
• CAS: 195261-00-8
• 化学式: C₂₄H₂₇N₃O₉
• 分子量: 501.493
• InChiKey: RAEZJQYCEIZDIG-UFYCRDLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  195
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N4-{O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->3)-[O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)]-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)}-L-asparaginyl-L-tyrosine methyl ester 、 (S)-2-{(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-3-hydroxy-propionylamino}-3-hydroxy-propionic acid 在 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 various solvent(s) 为溶剂， 以70%的产率得到N4-{O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->3)-[O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-α-D-mannopyranosyl-(1->6)]-O-β-D-mannopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)}-N2-(9-fluorenylmethoxycarbonyl-L-seryl-L-seryl-L-seryl)-L-asparaginyl-L-tyrosine methyl ester
  参考文献：
  名称：

  Building blocks for glycoproteins: Synthesis of the ribonuclease B fragment 21–25 containing an undecasaccharide N-glycan

  摘要：

  A glycosylated fragment of the bovine glycoprotein ribonuclease B (1) was synthesized corresponding to amino acids 21-25 with a complex type biantennary N-glycan linked to Asn(24). The total synthesis of the undecasaccharide-glycopentapeptide 1 was accomplished by modem solution phase glycopeptide chemistry combined with enzymatic techniques for the removal of protective groups and a regio- and stereoselective transfer of the terminal carbohydrates using glycosyltransferases. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01278-1
• 作为产物：
  描述：

  2-[[2-[(2-氨基-3-羟基-丙酰)氨基]-3-羟基-丙酰]氨基]-3-羟基-丙酸 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 三乙胺 作用下， 生成 (S)-2-{(S)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-propionylamino]-3-hydroxy-propionylamino}-3-hydroxy-propionic acid
  参考文献：
  名称：

  Building blocks for glycoproteins: Synthesis of the ribonuclease B fragment 21–25 containing an undecasaccharide N-glycan

  摘要：

  A glycosylated fragment of the bovine glycoprotein ribonuclease B (1) was synthesized corresponding to amino acids 21-25 with a complex type biantennary N-glycan linked to Asn(24). The total synthesis of the undecasaccharide-glycopentapeptide 1 was accomplished by modem solution phase glycopeptide chemistry combined with enzymatic techniques for the removal of protective groups and a regio- and stereoselective transfer of the terminal carbohydrates using glycosyltransferases. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01278-1

文献信息

• Building blocks for glycoproteins: Synthesis of the ribonuclease B fragment 21–25 containing an undecasaccharide N-glycan
  作者：Carlo Unverzagt

  DOI：10.1016/s0040-4039(97)01278-1

  日期：1997.8

  A glycosylated fragment of the bovine glycoprotein ribonuclease B (1) was synthesized corresponding to amino acids 21-25 with a complex type biantennary N-glycan linked to Asn(24). The total synthesis of the undecasaccharide-glycopentapeptide 1 was accomplished by modem solution phase glycopeptide chemistry combined with enzymatic techniques for the removal of protective groups and a regio- and stereoselective transfer of the terminal carbohydrates using glycosyltransferases. (C) 1997 Elsevier Science Ltd.