methylamide of N-t-butyloxycarbonyl-L-methionine | 68800-01-1

• 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: methylamide of N-t-butyloxycarbonyl-L-methionine
• 英文别名: Boc-Met-NHCH3；tert-butyl N-[(2S)-1-(methylamino)-4-methylsulfanyl-1-oxobutan-2-yl]carbamate
• CAS: 68800-01-1
• 化学式: C₁₁H₂₂N₂O₃S
• 分子量: 262.373
• InChiKey: FYOUTJSPFQTMTQ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methylamide of N-t-butyloxycarbonyl-L-methionine 在 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 26.0h， 生成 Boc-Leu-Met-NHCH3
  参考文献：
  名称：

  Structure-activity studies on the C-terminal amide of substance P

  摘要：

  Twelve C-terminal heptapeptide analogues of substance P have been synthesized by solid phase and by the classical solution method. The modifications concerned all the C-terminal primary amide of SP and should therefore help to understand the biological significance of this carboxamide, as evaluated by in vivo and in vitro bioassays. From the results it can be seen that not the slightest change of the two amide protons is tolerated without an important loss of activity: replacement of one or two amide protons with alkyl groups, extension of the amide to the hydrazide and its alkyl analogues, and exchange of the amide with an ester or a carboxylic acid all reduce the relative activity/affinity at least by 2-fold. It is not clear for what reason all these modifications produce such a drastic activity reduction.

  DOI：

  10.1021/jm00353a009
• 作为产物：
  描述：

  N-叔丁氧羰基-L-蛋氨酸二环己胺盐 以 四氢呋喃 、 水 为溶剂， 反应 0.03h， 生成 methylamide of N-t-butyloxycarbonyl-L-methionine
  参考文献：
  名称：

  Structure-activity studies on the C-terminal amide of substance P

  摘要：

  Twelve C-terminal heptapeptide analogues of substance P have been synthesized by solid phase and by the classical solution method. The modifications concerned all the C-terminal primary amide of SP and should therefore help to understand the biological significance of this carboxamide, as evaluated by in vivo and in vitro bioassays. From the results it can be seen that not the slightest change of the two amide protons is tolerated without an important loss of activity: replacement of one or two amide protons with alkyl groups, extension of the amide to the hydrazide and its alkyl analogues, and exchange of the amide with an ester or a carboxylic acid all reduce the relative activity/affinity at least by 2-fold. It is not clear for what reason all these modifications produce such a drastic activity reduction.

  DOI：

  10.1021/jm00353a009

文献信息

• Plucinski, Tomasz; Rolka, Krzysztof; Baran, Leokadia, Polish Journal of Chemistry, 1983, vol. 57, # 7/8/9, p. 887 - 897
  作者：Plucinski, Tomasz、Rolka, Krzysztof、Baran, Leokadia、Przegalinski, Edmund、Kupryszewski, Gotfryd

  DOI：——

  日期：——
• Structure-activity studies on the C-terminal amide of substance P
  作者：Emanuel Escher、Rejean Couture、Constantinos Poulos、Nikos Pinas、Jacques Mizrahi、Dimitrios Theodoropoulos、Domenico Regoli

  DOI：10.1021/jm00353a009

  日期：1982.11

  Twelve C-terminal heptapeptide analogues of substance P have been synthesized by solid phase and by the classical solution method. The modifications concerned all the C-terminal primary amide of SP and should therefore help to understand the biological significance of this carboxamide, as evaluated by in vivo and in vitro bioassays. From the results it can be seen that not the slightest change of the two amide protons is tolerated without an important loss of activity: replacement of one or two amide protons with alkyl groups, extension of the amide to the hydrazide and its alkyl analogues, and exchange of the amide with an ester or a carboxylic acid all reduce the relative activity/affinity at least by 2-fold. It is not clear for what reason all these modifications produce such a drastic activity reduction.