tert-butoxycarbonyl-γ-benzyl-L-glutamyl-L-phenylalanine methyl ester | 114671-00-0

• 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: tert-butoxycarbonyl-γ-benzyl-L-glutamyl-L-phenylalanine methyl ester
• 英文别名: Boc-Glu(OBn)-Phe-OMe；benzyl (4S)-5-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate
• CAS: 114671-00-0
• 化学式: C₂₇H₃₄N₂O₇
• 分子量: 498.576
• InChiKey: WPOWABXCIDJCMF-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butoxycarbonyl-γ-benzyl-L-glutamyl-L-phenylalanine methyl ester 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 trifluoroacetyl-L-glutamyl-L-phenylalanine methyl ester
  参考文献：
  名称：

  Peptide sweeteners. 5. Side chain homologs relating zwitterionic and trifluoroacetylated amino acid anilide and dipeptide sweeteners

  摘要：

  Side-chain homologues of sweet trifluoroacetyl-alpha-L-aspartyl-p-cyanoanilide have been synthesized and tasted. Removal of the trifluoroacetyl group only changes the potency of sweet taste, not the taste property. These results have been compared with the structure-taste relationships of dipeptide sweeteners. An informative discontinuity of taste effects was found to exist with novel aminomalonyl dipeptide derivatives. The results are explained on topochemical grounds.

  DOI：

  10.1021/jm00346a013
• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-苄酯 、 L-苯丙氨酸甲酯 生成 tert-butoxycarbonyl-γ-benzyl-L-glutamyl-L-phenylalanine methyl ester
  参考文献：
  名称：

  CHEN, SHUI-TEIN;WANG, KUNG-TSUNG, J. CHEM. RES. SYNOP.,(1987) N 9, 308-309

  摘要：

  DOI：

文献信息

• Synthesis and activity of HIV protease inhibitors
  作者：Patrick Garrouste、Macek Pawlowski、Thierry Tonnaire、Sames Sicsic、Pascal Dumy、Eve de Rosny、Michèle Reboud-Ravaux、Pierre Fulcrand、Jean Martinez

  DOI：10.1016/s0223-5234(98)80043-3

  日期：1998.6

  We report here the synthesis and activity of HIV protease inhibitors. Ln the first stage hydrophobic compounds incorporating a 'carba' bond surrogate or a beta-homologated residue were synthesized. Secondly, we synthesized cyclic compounds in which we incorporated 2-quinoline carboxylic acid in the P3 position and the amino-hydroxyindane moiety in the P'3. The last part of this work was dedicated to a structure/activity study of a peptide substrate. These modifications allowed us to work up the synthesis of new pseudopeptide bonds: amino-amide and hydroxy-amide, Compounds with activity in the micromolar range were actually a starting point for the synthesis of new protease inhibitors. (C) Elsevier, Paris.