N-(N-benzyloxycarbonyl-L-tyrosyl)-L-serine | 20448-71-9

• 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: N-(N-benzyloxycarbonyl-L-tyrosyl)-L-serine
• 英文别名: N-(N-Benzyloxycarbonyl-L-tyrosyl)-L-serin；N-Benzyloxycarbonyl-L-tyrosyl=>-L-serin；Z-Tyr-Ser-OH；(2S)-3-hydroxy-2-[[(2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoic acid
• CAS: 20448-71-9
• 化学式: C₂₀H₂₂N₂O₇
• 分子量: 402.404
• InChiKey: LZMMFOXOCHALJU-IRXDYDNUSA-N

物化性质

• 熔点：
  148 °C
• 沸点：
  775.7±60.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(N-benzyloxycarbonyl-L-tyrosyl)-L-serine 在 甲醇 、 钯 、 溶剂黄146 作用下， 生成 H-Tyr-Ser-OH
  参考文献：
  名称：

  Synth�se du N-ac�tyl-L-s�ryl-L-tyrosyl-L-s�ryl-L-m�thionyl-?-L-glutamate de benzyle et de peptides apparent�s

  摘要：

  AbstractN‐CBO‐L‐Seryl‐L‐tyrosyl‐L‐serine methyl ester and L‐methionyl‐γ‐benzyl‐L‐glutamate are prepared by different methods. Condensation by the hydrazideazide procedure affords N‐CBO‐L‐seryl‐L‐tyrosyl‐L‐seryl‐L‐methionyl‐γ‐benzyl‐L‐glutamate, which is shown to be optically pure by leucine‐aminopeptidase digestion. Transformation of the above N‐CBO‐tripeptide ester to the N‐acetyltripeptide ester and condensation by the hydrazide‐azide procedure with the above dipeptide gives N‐acetyl‐L‐seryl‐L‐tyrosyl‐L‐seryl‐L‐methionyl‐γ‐benzyl‐L‐glutamate. The effects produced in the course of fissure of CBO‐ and benzyl‐groups from peptides containing serine and methionine residues, using HBr and acetic acid, are studied.

  DOI：

  10.1002/hlca.19580410640
• 作为产物：
  描述：

  N-苄氧羰基-L-酪氨酸 在 sodium hydroxide 、 乙酸乙酯 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 乙腈 作用下， 生成 N-(N-benzyloxycarbonyl-L-tyrosyl)-L-serine
  参考文献：
  名称：

  Synth�se du N-ac�tyl-L-s�ryl-L-tyrosyl-L-s�ryl-L-m�thionyl-?-L-glutamate de benzyle et de peptides apparent�s

  摘要：

  AbstractN‐CBO‐L‐Seryl‐L‐tyrosyl‐L‐serine methyl ester and L‐methionyl‐γ‐benzyl‐L‐glutamate are prepared by different methods. Condensation by the hydrazideazide procedure affords N‐CBO‐L‐seryl‐L‐tyrosyl‐L‐seryl‐L‐methionyl‐γ‐benzyl‐L‐glutamate, which is shown to be optically pure by leucine‐aminopeptidase digestion. Transformation of the above N‐CBO‐tripeptide ester to the N‐acetyltripeptide ester and condensation by the hydrazide‐azide procedure with the above dipeptide gives N‐acetyl‐L‐seryl‐L‐tyrosyl‐L‐seryl‐L‐methionyl‐γ‐benzyl‐L‐glutamate. The effects produced in the course of fissure of CBO‐ and benzyl‐groups from peptides containing serine and methionine residues, using HBr and acetic acid, are studied.

  DOI：

  10.1002/hlca.19580410640

文献信息

• Synth�se du N-ac�tyl-L-s�ryl-L-tyrosyl-L-s�ryl-L-m�thionyl-?-L-glutamate de benzyle et de peptides apparent�s
  作者：St. Guttmann、R. A. Boissonnas

  DOI：10.1002/hlca.19580410640

  日期：——

  AbstractN‐CBO‐L‐Seryl‐L‐tyrosyl‐L‐serine methyl ester and L‐methionyl‐γ‐benzyl‐L‐glutamate are prepared by different methods. Condensation by the hydrazideazide procedure affords N‐CBO‐L‐seryl‐L‐tyrosyl‐L‐seryl‐L‐methionyl‐γ‐benzyl‐L‐glutamate, which is shown to be optically pure by leucine‐aminopeptidase digestion. Transformation of the above N‐CBO‐tripeptide ester to the N‐acetyltripeptide ester and condensation by the hydrazide‐azide procedure with the above dipeptide gives N‐acetyl‐L‐seryl‐L‐tyrosyl‐L‐seryl‐L‐methionyl‐γ‐benzyl‐L‐glutamate. The effects produced in the course of fissure of CBO‐ and benzyl‐groups from peptides containing serine and methionine residues, using HBr and acetic acid, are studied.