Boc-Gly-Gly-Phe-Leu-OBzl | 69729-14-2

• 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: Boc-Gly-Gly-Phe-Leu-OBzl
• 英文别名: Boc-Gly-Gly-Phe-Leu-OBn；benzyl (2S)-4-methyl-2-[[(2S)-2-[[2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]pentanoate
• CAS: 69729-14-2
• 化学式: C₃₁H₄₂N₄O₇
• 分子量: 582.697
• InChiKey: IAPFDWZXPMWYCZ-DQEYMECFSA-N

物化性质

• 熔点：
  162-165 °C
• 沸点：
  833.2±65.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-Gly-Gly-Phe-Leu-OBzl 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 以99%的产率得到HCl*Gly-Gly-Phe-Leu-OBzl
  参考文献：
  名称：

  对环境无害 肽 液体辅助球合成铣削：在亮脑啡肽的合成中的应用

  摘要：

  本文介绍了一种原始的方法 肽 避免毒性的键合成 溶剂和反应物。球-铣削在存在下，Boc保护的α-氨基酸N-羧基酸酐（Boc-AA-NCA）或Boc保护的α-氨基酸N-羟基琥珀酰亚胺酯（Boc-AA-OSu）的化学计量的NaHCO 3和最少量的EtOAc导致生成二甲苯五肽以有效和环保的方式。该方法已成功应用于亮脑啡肽的合成。

  DOI：

  10.1039/c3gc40302e
• 作为产物：
  描述：

  L-亮氨酸苄基酯 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 甲苯 为溶剂， 反应 0.02h， 生成 Boc-Gly-Gly-Phe-Leu-OBzl
  参考文献：
  名称：

  MW‐Enhanced High‐Speed Deprotection of Boc Group Usingp‐TsOH and Concommitant Formation ofN‐Me‐Amino Acid Benzyl Esterp‐TsOH Salts

  摘要：

  A high-speed, complete deprotection of Boc group from Boc amino acids and protected peptide esters employing p-TsOH in toluene under microwave irradiation is found to be complete in 30 s. The deprotection can be carried out in methanol and acetonitrile also. Under the present conditions, C-peptide benzyl esters and O-benzyl ethers have been found to be stable. This has permitted us to carry out the synthesis of [Leu] enkephalin employing the Boc/Bzl-group strategy. Further more, it has been found that both N-alpha-Fmoc and N-alpha-Z groups are completely stable. The present conditions can be extended for the concomitant removal of the Boc group and the formation of C-benzyl amino acid esters as well. This has been utilized for the synthesis of N-Me amino acid benzyl esters starting from Boc-N-Me amino acids in a single step.

  DOI：

  10.1081/scc-200063953

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。
• <i>N</i>-Hydroxy Amides. III. Active Esters of Polystyrene-bound 1-Hydroxy-2-pyrrolidinone and Their Use in Peptide Synthesis
  作者：Masayasu Akiyama、Kazuyuki Shimizu、Seiichi Aiba、Hiroaki Katoh

  DOI：10.1246/bcsj.58.1421

  日期：1985.5

  dicyclohexylcarbodiimide (DCC) as a condensing agent. Several N-blocked α-amino acids have been loaded on this resin by use of DCC. The amino acid resin can be utilized for peptide synthesis. Repetitive usage of the resin in the form of esters and facile synthesis of a biologically active pentapeptide, Leu5-enkephalin, show the usefulness of the polymer-bound 1-hydroxy-2-pyrrolidinone.

  使用二环己基碳二亚胺 (DCC) 作为缩合剂，通过氨基甲基化共聚（苯乙烯-2% 二乙烯基苯）与 1-羟基-5-氧代-3-吡咯烷羧酸反应制备了聚合物键环状 N-羟基酰胺。通过使用 DCC，已将几种 N 封闭的 α-氨基酸加载到该树脂上。氨基酸树脂可用于肽合成。以酯的形式重复使用树脂并轻松合成具有生物活性的五肽 Leu5-脑啡肽，显示了聚合物结合的 1-羟基-2-吡咯烷酮的有用性。
• Clausen, Kim; Thorsen, Michael; Lawesson, Sven-Olov, Journal of the Chemical Society. Perkin transactions I, 1984, # 4, p. 785 - 798
  作者：Clausen, Kim、Thorsen, Michael、Lawesson, Sven-Olov、Spatola, Arno F.

  DOI：——

  日期：——
• Synthesis of 15N-Labelled Leu-Enkephalins.
  作者：Fredrik Degerbeck、Bengt Fransson、Leif Grehn、Ulf Ragnarsson、J. Pietrzak、Jan Arnarp、Lars Björk、Ryszard Gawinecki

  DOI：10.3891/acta.chem.scand.49-0149

  日期：——
• Synthesis of enkephalins by the method of polymeric activated esters based on 4-hydroxy-3-nitrobenzophenone
  作者：E. I. Grigor'ev、S. V. Chernova

  DOI：10.1007/bf00597660

  日期：1989.7