H-Gly-Gly-Phe-Leu-OBzl | 69729-07-3

• 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: H-Gly-Gly-Phe-Leu-OBzl
• 英文别名: H-Gly-Gly-Phe-Leu-OBn；Gly-Gly-Phe-Leu-OBzl；benzyl (2S)-2-[[(2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoate
• CAS: 69729-07-3
• 化学式: C₂₆H₃₄N₄O₅
• 分子量: 482.58
• InChiKey: ITJUGITWYHQCES-VXKWHMMOSA-N

物化性质

• 熔点：
  154-156 °C
• 沸点：
  775.7±60.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  H-Gly-Gly-Phe-Leu-OBzl 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Bis(BOC) amino acid fluorides as reactive peptide coupling reagents

  摘要：

  DOI：

  10.1021/jo00067a067
• 作为产物：
  描述：

  L-苯基丙氨酸叔丁酯 在 氯化亚砜 、 碳酸氢钠 、 4-氨甲基哌啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 6.0h， 生成 H-Gly-Gly-Phe-Leu-OBzl
  参考文献：
  名称：

  Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group

  摘要：

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

  DOI：

  10.1021/jo982141d

文献信息

• Method of producing peptide
  申请人：Murao Hiroshi

  公开号：US08716439B2

  公开（公告）日：2014-05-06

  The present invention is related to a method of producing a peptide, characterized in contacting a reaction mixture with a base after a condensation reaction to hydrolyze while a basic condition is maintained until a ratio of a remaining unreacted active ester of an acid component is decreased to 1% or less in a liquid phase peptide synthesis method. According to the invention, a target peptide of high purity can be simply and efficiently produced by a continuous liquid phase synthesis method. Further, the present invention is related to a method of producing a peptide, characterized in using an amide-type solvent immiscible with water in a liquid phase peptide synthesis method. According to the invention, various peptides can be produced by the liquid phase synthesis method without being restricted by the amino acid sequence of the target peptide.

  本发明涉及一种肽的生产方法，其特征在于在缩合反应后将反应混合物与碱接触以在液相肽合成方法中在保持碱性条件的同时水解，直到酸组分的剩余未反应活性酯的比率降至1％或更低。根据本发明，可以通过连续液相合成方法简单高效地生产高纯度的目标肽。此外，本发明涉及一种肽的生产方法，其特征在于在液相肽合成方法中使用与水不相溶的酰胺型溶剂。根据本发明，可以通过液相合成方法生产各种肽，而不受目标肽的氨基酸序列的限制。
• Amino acids and peptides. IX. Synthetic studies on Leu-enkephalin analogues containing a ureylene bond.
  作者：KOICHI KAWASAKI、MITSUKO MAEDA、JOE WATANABE、HIROSHI KANETO

  DOI：10.1248/cpb.36.1766

  日期：——

  Leu-enkephalin analogues containing a ureylene bond instead of an amide bond were synthesized. The ureylene bond was formed by a coupling reaction of the isocyanate derived from the corresponding azide by Curtius rearrangement reaction. Three analogues, each of which has a ureylene bond at the Tyr-Gly or Gly-Gly or Phe-Leu amide bond, were prepared. The ureylene bond resisted enzymatic hydrolysis, but the biological activities of the synthetic peptides on guinea pig ileum and mouse was deferens were low compared with those of Leu-enkephalin.

  我们合成了含有脲键而非酰胺键的亮烯酮类似物。脲烯键是由相应叠氮化物中的异氰酸酯通过库尔提斯重排反应偶联生成的。制备了三种类似物，每种都在 Tyr-Gly、Gly-Gly 或 Phe-Leu 酰胺键上有一个脲烯键。脲烯键可抗酶水解，但合成肽在豚鼠回肠和小鼠输精管上的生物活性低于Leu-enkephalin。
• (Fluoren-9-ylmethoxy)carbonyl (Fmoc) amino acid chlorides. Synthesis, characterization, and application to the rapid synthesis of short peptide segments
  作者：Louis A. Carpino、Beri J. Cohen、Kenton E. Stephens、S. Yahya Sadat-Aalaee、Jien Heh Tien、Denton C. Langridge

  DOI：10.1021/jo00369a042

  日期：1986.9
• Kawasaki, Koichi; Tsuji, Toshiki; Maeda, Misuko, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 3, p. 1044 - 1048
  作者：Kawasaki, Koichi、Tsuji, Toshiki、Maeda, Misuko、Matsumoto, Tatsuya、Hirase, Katsuhiko

  DOI：——

  日期：——
• Tris(2-aminoethyl)amine as substitute for 4-(aminomethyl)piperidine in the FMOC/polyamine approach to rapid peptide synthesis
  作者：Louis A. Carpino、Dean Sadat-Aalaee、Michael Beyermann

  DOI：10.1021/jo00292a050

  日期：1990.3