N-[N-(N-tert-butoxycarbonyl-β-alanyl)-L-leucyl]-L-phosphotryptophan diethyl ester | 850463-68-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: N-[N-(N-tert-butoxycarbonyl-β-alanyl)-L-leucyl]-L-phosphotryptophan diethyl ester
• 英文别名: tert-butyl N-[3-[[(2S)-1-[[(1R)-1-diethoxyphosphoryl-2-(1H-indol-3-yl)ethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-oxopropyl]carbamate
• CAS: 850463-68-2
• 化学式: C₂₈H₄₅N₄O₇P
• 分子量: 580.662
• InChiKey: HOGHGIOJVJUPOG-UKILVPOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  148
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[N-(N-tert-butoxycarbonyl-β-alanyl)-L-leucyl]-L-phosphotryptophan diethyl ester 在 N,O-双三甲硅基乙酰胺 、 碘代三甲硅烷 、 水 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.33h， 以77%的产率得到N-(N-β-alanyl-L-leucyl)-L-phosphotryptophan
  参考文献：
  名称：

  Synthesis and evaluation of new tripeptide phosphonate inhibitors of MMP-8 and MMP-2

  摘要：

  The phosphotryptophan derivative L-Pro-L-LeU-L-(P)Trp(OH)(2) (2b) was reported as the first example of left-hand-side(1) phosphonate inhibitor of MMP-8. Its uncommon mode of binding to MMP-8 was mainly ascribed to the presence of the proline residue in P, Ten new analogues of 2b were obtained by replacement of the aminoterminal L-Pro with aminoacid residues bearing small side chains. Most of the new analogues show an increase of affinity for MMP-2 and MMP-8, and different profiles of selectivity. Computer simulations were performed to explain the effects of substitutions on the preferred mode of binding. They reveal that most of the new analogues are probably accommodated in the right. rather than left-hand side of MMP-8 active site. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.10.013
• 作为产物：
  描述：

  N-(N-benzyloxycarbonyl-L-leucyl)-L-phosphotryptophan diethyl ester 在 palladium on activated charcoal ammonium formate 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-[N-(N-tert-butoxycarbonyl-β-alanyl)-L-leucyl]-L-phosphotryptophan diethyl ester
  参考文献：
  名称：

  Synthesis and evaluation of new tripeptide phosphonate inhibitors of MMP-8 and MMP-2

  摘要：

  The phosphotryptophan derivative L-Pro-L-LeU-L-(P)Trp(OH)(2) (2b) was reported as the first example of left-hand-side(1) phosphonate inhibitor of MMP-8. Its uncommon mode of binding to MMP-8 was mainly ascribed to the presence of the proline residue in P, Ten new analogues of 2b were obtained by replacement of the aminoterminal L-Pro with aminoacid residues bearing small side chains. Most of the new analogues show an increase of affinity for MMP-2 and MMP-8, and different profiles of selectivity. Computer simulations were performed to explain the effects of substitutions on the preferred mode of binding. They reveal that most of the new analogues are probably accommodated in the right. rather than left-hand side of MMP-8 active site. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.10.013