ethyl (S,Z)-4-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate | 1207718-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (S,Z)-4-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate
• 英文别名: Boc-zdγPhe-OEt；(S,Z)-ethyl-4-tert-butoxycarbonylamino-5-phenylpent-2-enoate；ethyl (Z,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpent-2-enoate
• CAS: 1207718-84-0
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: OFLTYWJABWDXRC-QYMJWVLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 、 二苯氧基磷基乙酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 、 水 、 sodium chloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以53%的产率得到ethyl (S,Z)-4-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate
  参考文献：
  名称：

  Michael Acceptor Based Antiplasmodial and Antitrypanosomal Cysteine Protease Inhibitors with Unusual Amino Acids

  摘要：

  New peptidic Michael acceptor based cysteine protease inhibitors displaying antiparasitic activity were identified by testing a broad series of 45 compounds in total, containing Asn, Gln, or Phe. As target enzymes, falcipain-2 and -3 from P. falciparum and rhodesain from T. b. rhodesiense were used. In the case of the Asn/Gln containing compounds, the trityl-protected, diastereomeric E-configured vinylogous dipeptide esters 16 (Boc-(S)-Phg-(R/S)-vGln(Trt)-OEt) were discovered as most active inhibitors concerning both protease inhibition and antiparasitic acitivity, with inhibition constants in the submicromolar range. The Compounds were shown to display time-dependent and competitive inhibition. In the case of the Phe containing Compounds, the maleic acid derivatives 42 and 43 (BnO-Phe <- Mal-Phe-OBn, BnO-Phe <- Mal-Phe-Ala-OBn. Mal = maleic acid) displayed good inhibition of rhodesain as well as good antitrypanosomal activity, while the fumaric acid derived E-analogue 14 (BnO-Phe <- Fum-Phe-OBn) only displayed inhibition or the target enzymes but no antiparasitic activity. Inhibition by these Phe derivatives was shown to be time-independent and competitive.

  DOI：

  10.1021/jm900946n

文献信息

• Non-classical Helices with<i>cis</i>Carbon-Carbon Double Bonds in the Backbone: Structural Features of α,γ-Hybrid Peptide Foldamers
  作者：Mothukuri Ganesh Kumar、Varsha J. Thombare、Mona M. Katariya、Kuruva Veeresh、K. Muruga Poopathi Raja、Hosahudya N. Gopi

  DOI：10.1002/anie.201602861

  日期：2016.6.27

  The impact of geometrically constrained cis α,β‐unsaturated γ‐amino acids on the folding of α,γ‐hybrid peptides was investigated. Structure analysis in single crystals and in solution revealed that the cis carbon–carbon double bonds can be accommodated into the 12‐helix without deviation from the overall helical conformation. The helical structures are stabilized by 4→1 hydrogen bonding in a similar

  研究了几何约束的顺式α，β-不饱和γ-氨基酸对α，γ-杂合肽折叠的影响。对单晶和溶液的结构分析表明，顺式碳-碳双键可以容纳在12螺旋中，而不会偏离整体螺旋构象。螺旋结构通过4→1氢键稳定，与β肽的12个螺旋和3个10个α肽的螺旋相似。这些结果表明，功能性顺式碳-碳双键可以容纳在螺旋肽的骨架中。