(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[1-(tert-butyl-dimethyl-silanyl)-1H-indol-3-yl]-propionic acid | 185448-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[1-(tert-butyl-dimethyl-silanyl)-1H-indol-3-yl]-propionic acid
• 英文别名: Boc-D-N(Me)Trp(TBDMS)(TBDMS)-OH；(2R)-3-[1-[tert-butyl(dimethyl)silyl]indol-3-yl]-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid
• CAS: 185448-79-7
• 化学式: C₂₃H₃₆N₂O₄Si
• 分子量: 432.635
• InChiKey: QKTLLEZUAWKBSE-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[1-(tert-butyl-dimethyl-silanyl)-1H-indol-3-yl]-propionic acid 在 盐酸 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 silica gel 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.08h， 生成 Me-Tyr(Bn)-OVal-N(Me)Val-OVal-D-N(Me)Trp-OOrn(Cbz)(Cbz)-OH
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Depsipeptide Mimic of Tendamistat

  摘要：

  The cyclic hexadepsipeptide framework of enniatin B was identified as a template matching the beta-turn tripeptide of tendamistat. The modified analog 1 was synthesized as a tendamistat mimic and compared to the acyclic derivative 2 and the tripeptide Ac-Try-Arg-Tyr-OMe. These compounds were assembled from the dimeric esters 3-5. As an inhibitor of alpha-amylase, 1 is twice as potent as 2 and comparable to the tripeptide. NMR studies of 1 reveal four conformers in equilibrium in a 50:25:15:10 ratio; the ring conformation of the major component is similar to that of the enniatin B template, with the cis geometry of the alpha-hydroxyisovaleryl-N-methylvaline amide linkage; the other conformers differ in the position or presence of the cis amide linkage.

  DOI：

  10.1021/jo9616062
• 作为产物：
  描述：

  BOC-D-色氨酸 在 sodium hydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 生成 (R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[1-(tert-butyl-dimethyl-silanyl)-1H-indol-3-yl]-propionic acid
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Depsipeptide Mimic of Tendamistat

  摘要：

  The cyclic hexadepsipeptide framework of enniatin B was identified as a template matching the beta-turn tripeptide of tendamistat. The modified analog 1 was synthesized as a tendamistat mimic and compared to the acyclic derivative 2 and the tripeptide Ac-Try-Arg-Tyr-OMe. These compounds were assembled from the dimeric esters 3-5. As an inhibitor of alpha-amylase, 1 is twice as potent as 2 and comparable to the tripeptide. NMR studies of 1 reveal four conformers in equilibrium in a 50:25:15:10 ratio; the ring conformation of the major component is similar to that of the enniatin B template, with the cis geometry of the alpha-hydroxyisovaleryl-N-methylvaline amide linkage; the other conformers differ in the position or presence of the cis amide linkage.

  DOI：

  10.1021/jo9616062

文献信息

• Design, Synthesis, and Evaluation of a Depsipeptide Mimic of Tendamistat
  作者：Andrea M. Sefler、Marisa C. Kozlowski、Tao Guo、Paul A. Bartlett

  DOI：10.1021/jo9616062

  日期：1997.1.1

  The cyclic hexadepsipeptide framework of enniatin B was identified as a template matching the beta-turn tripeptide of tendamistat. The modified analog 1 was synthesized as a tendamistat mimic and compared to the acyclic derivative 2 and the tripeptide Ac-Try-Arg-Tyr-OMe. These compounds were assembled from the dimeric esters 3-5. As an inhibitor of alpha-amylase, 1 is twice as potent as 2 and comparable to the tripeptide. NMR studies of 1 reveal four conformers in equilibrium in a 50:25:15:10 ratio; the ring conformation of the major component is similar to that of the enniatin B template, with the cis geometry of the alpha-hydroxyisovaleryl-N-methylvaline amide linkage; the other conformers differ in the position or presence of the cis amide linkage.