N-tert-butoxycarbonyl-S-p-methoxybenzyl-L-homocysteine | 169474-11-7

• 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: N-tert-butoxycarbonyl-S-p-methoxybenzyl-L-homocysteine
• 英文别名: N-α-Boc-(4-MeBzl)homocysteine；Boc-hCys(Mob)-OH；(2S)-4-[(4-methoxyphenyl)methylsulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 169474-11-7
• 化学式: C₁₇H₂₅NO₅S
• 分子量: 355.455
• InChiKey: KNUSSPBWPANBCF-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-异亮酰胺盐酸盐 、 N-tert-butoxycarbonyl-S-p-methoxybenzyl-L-homocysteine 在 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到N-tert-butoxycarbonyl-S-p-methoxybenzyl-L-homocysteinylisoleucyl amide
  参考文献：
  名称：

  Synthesis of Orthogonally Protected L-Homocysteine and L-2-Amino-4-phosphonobutanoic Acid from L-Homoserine

  摘要：

  文中介绍了从市售 L-高丝氨酸中方便合成 N-叔丁氧羰基-S-对甲氧基苄基-L-高丝氨酸苄酯和 L-4-二甲基膦酰基-2-N-邻苯二甲酰亚胺丁酸苄酯的方法，以及将它们掺入二肽的方法。

  DOI：

  10.1055/s-1995-4015
• 作为产物：
  描述：

  benzyl N-tert-butoxycarbonyl-S-p-methoxybenzyl-L-homocysteinate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 以76%的产率得到N-tert-butoxycarbonyl-S-p-methoxybenzyl-L-homocysteine
  参考文献：
  名称：

  Synthesis of Orthogonally Protected L-Homocysteine and L-2-Amino-4-phosphonobutanoic Acid from L-Homoserine

  摘要：

  文中介绍了从市售 L-高丝氨酸中方便合成 N-叔丁氧羰基-S-对甲氧基苄基-L-高丝氨酸苄酯和 L-4-二甲基膦酰基-2-N-邻苯二甲酰亚胺丁酸苄酯的方法，以及将它们掺入二肽的方法。

  DOI：

  10.1055/s-1995-4015

文献信息

• Novel Cyclic Analogs of Angiotensin II with Cyclization between Positions 5 and 7:  Conformational and Biological Implications
  作者：Wei-Jun Zhang、Gregory V. Nikiforovich、Jacqueline Pérodin、Darren E. Richard、Emanuel Escher、Garland R. Marshall

  DOI：10.1021/jm9507744

  日期：1996.1.1

  To study the conformational features of molecular recognition of angiotensin II (Asp1-Arg2-Val3-Tyr4-Val/IIe5-His6-Pro7-Phe8, AII), the synthesis and biological testing of several cyclic analogs of AII cyclized between positions 5 and 7 have been performed. The synthesized analogs were Sar1-Arg2-Val3-Tyr4-cyclo(Cys5-His6-Pen7)-Phe8 (3), Sar1-Arg2-Val3-Tyr4-cyclo(Asp5-His6-Apt7)-Phe8 (4), Sar1-Arg2

  为了研究血管紧张素II（Asp1-Arg2-Val3-Tyr4-Val / IIe5-His6-Pro7-Phe8，AII）的分子识别的构象特征，合成和生物学测试了几种AII环状类似物，它们在位置5和7之间循环已经执行了。合成的类似物是Sar1-Arg2-Val3-Tyr4-环（Cys5-His6-Pen7）-Phe8（3），Sar1-Arg2-Val3-Tyr4-环（Asp5-His6-Apt7）-Phe8（4），Sar1- Arg2-Val3-Tyr4-环（Glu5-His6-Apt7）-Phe8（5），Sar1-Arg2-Val3-Tyr4-环-（Cys5-His6-Mpt7）-Phe8（6），Sar1-Arg2-Val3-Tyr4 -环（Cys5-His6-Mpc7）-Phe8（7），Sar1-Arg2-Val3-Tyr4-环（Hcy5-His6-Mpt7）-Phe8（8）和Sar
• Ring Size in Octreotide Amide Modulates Differently Agonist versus Antagonist Binding Affinity and Selectivity
  作者：Christy Rani R. Grace、Judit Erchegyi、Manoj Samant、Renzo Cescato、Veronique Piccand、Roland Riek、Jean Claude Reubi、Jean E. Rivier

  DOI：10.1021/jm701445q

  日期：2008.5.1

  H-DPhe(2)-c[Cys(3) -Phe(7) -DTrp(8)-Lys(9)-Thr(10)-Cys(14)] -Thr(15) -NH(2) (1) (a somatostatin agonist, SRIF numbering) and H-Cpa(2) -c[DCys(3) -Tyr(7) -DTrp(8)-Lys(9)-Thr(10)-Cys(14)] -Nal(15)-NH(2) (4) (a somatostatin antagonist) are based on the structure of octreotide that binds to three somatostatin receptor subtypes (SSt(2/3/5)) with significant binding affinity. Analogues of 1 and 4 were synthesized with norcysteine (Ncy), homocysteine (Hcy), or D-homocysteine (DHcy) at positions 3 and/or 14. Introducing Ncy at positions 3 and 14 constrained the backbone flexibility, resulting in loss of binding affinity at all sst(s) The introduction of Hey at positions 3 and 14 improved selectivity for sst(2) as a result of significant loss of binding affinity at the other ssts. Substitution by DHcy at position 3 in the antagonist scaffold (5), on the other hand, resulted in a significant loss of binding affinity at sst(2) and sst(3) as compared to the different affinities of the parent compound (4). The 3D NMR structures of the analogues in dimethylsulfoxide are consistent with the observed binding affinities.
• Ring Size of Somatostatin Analogues (ODT-8) Modulates Receptor Selectivity and Binding Affinity
  作者：Judit Erchegyi、Christy Rani R. Grace、Manoj Samant、Renzo Cescato、Veronique Piccand、Roland Riek、Jean Claude Reubi、Jean E. Rivier

  DOI：10.1021/jm701444y

  日期：2008.5.1

  The synthesis, biological testing, and NMR studies of several analogues of H-c[Cys(3) -Phe(6) -Phe(7) -DTrp(8)- Lys(9)-Thr(10)-Phe(11)-CYS(14)] -OH (ODT-8, a pan-somatostatin analogue, 1) have been performed to assess the effect of changing the stereochemistry and the number of atoms in the disulfide bridge on binding affinity. Cysteine at positions 3 and/or 14 (somatostatin numbering) were/was substituted with D-Cysteine, norcysteine, D-norcysteine, homocysteine, and/or D-homocysteine. The 3D structure analysis of selected partially selective, bioactive analogues (3, 18, 19, and 21) was carried out in dim ethyl sulfoxide. Interestingly and not unexpectedly, the 3D structures of these analogues comprised the pharmacophore for which the analogues had the highest binding affinities (i.e., sst(4) in all cases).