methyl [N^α-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate | 251320-34-0

• 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: methyl [N^α-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate
• 英文别名: Boc-Lys(Cbz(2-Cl))-Ser-OMe；methyl (2S)-2-[[(2S)-6-[(2-chlorophenyl)methoxycarbonylamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]-3-hydroxypropanoate
• CAS: 251320-34-0
• 化学式: C₂₃H₃₄ClN₃O₈
• 分子量: 515.991
• InChiKey: MNTQVBCSMQJVAQ-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl [N^α-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate 在 劳森试剂 、 咪唑 、 四丁基氟化铵 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.42h， 生成 methyl (1'S,4S)-2-[1-(tert-butoxycarbonylamino)-5'-(2-chlorobenzyloxycarbonylamino)pentyl]-3-methyl-2-thiazolidine-4-carboxylate
  参考文献：
  名称：

  Solid phase synthesis of a ΨCH2NH pseudopeptide by ligation of a peptidyl aldehyde with a resin-bound amino peptide

  摘要：

  Solid phase synthesis of psi[CH2NH] pseudopeptide 3 was accomplished by reductive amination of peptidyl aldehyde 1 with resin bound amino peptide 2. No epimerization took place during the aldehyde preparation or the reductive amination step. This convergent strategy should facilitate the synthesis of analogues of the neuropeptide PACAP. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00689-4
• 作为产物：
  描述：

  L-丝氨酸甲酯盐酸盐 、 N-叔丁氧羰基-N'-(2-氯苄氧羰基)-L-赖氨酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到methyl [N^α-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate
  参考文献：
  名称：

  Solid phase synthesis of a ΨCH2NH pseudopeptide by ligation of a peptidyl aldehyde with a resin-bound amino peptide

  摘要：

  Solid phase synthesis of psi[CH2NH] pseudopeptide 3 was accomplished by reductive amination of peptidyl aldehyde 1 with resin bound amino peptide 2. No epimerization took place during the aldehyde preparation or the reductive amination step. This convergent strategy should facilitate the synthesis of analogues of the neuropeptide PACAP. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00689-4

文献信息

• Oxazole-Based Peptide Macrocycles:  A New Class of G-Quadruplex Binding Ligands
  作者：Katja Jantos、Raphaël Rodriguez、Sylvain Ladame、Pravin S. Shirude、Shankar Balasubramanian

  DOI：10.1021/ja064713e

  日期：2006.10.1

  Herein we report on the synthesis and DNA binding properties of a new class of water soluble oxazole-based peptide macrocycles that bind selectively to quadruplex DNA, with no detectable binding to duplex DNA. We have recently identified one quadruplex in the proto-oncogene c-kit that is suspected to act as a regulatory element for the expression of the c-kit gene. Here we provide the first example of a ligand binding to and stabilizing the c-kit quadruplex. Moreover, we show that these macrocycles show a preference for the c-kit quadruplex as compared to the human telomeric quadruplex.