H-Gly-Phe-Leu-OBzl | 73994-89-5

• 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-Phe-Leu-OBzl
• 英文别名: Gly-Phe-Leu-OBzl；benzyl (2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-phenylpropanoyl]amino]-4-methylpentanoate
• CAS: 73994-89-5
• 化学式: C₂₄H₃₁N₃O₄
• 分子量: 425.528
• InChiKey: LZGLBSIPEQQKIF-SFTDATJTSA-N

物化性质

• 熔点：
  168-170 °C
• 沸点：
  665.7±55.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  110.52
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  H-Gly-Phe-Leu-OBzl 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 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：

  Boc2-Gly-Phe-Leu-OBzl 在 三氟乙酸 作用下， 反应 1.0h， 生成 H-Gly-Phe-Leu-OBzl
  参考文献：
  名称：

  Gunnarsson, Kerstin; Ragnarsson, Ulf, Acta Chemica Scandinavica, 1990, vol. 44, # 7, p. 944 - 951

  摘要：

  DOI：

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。
• Studies on peptides. CXXXI. Synthesis of adrenorphin and enkephalin analogs.
  作者：NOBUTAKA FUJII、MITSUYA SAKURAI、SUZUMITSU KUNO、HARUAKI YAJIMA、MASAMICHI SATOH、MARIKO MATSUSHITA、NORIKO YAMAMOTO、HIROSHI TAKAGI、ZENGMU WANG、WI LEE、PENFENG WANG

  DOI：10.1248/cpb.33.4326

  日期：——

  Adrenorphin, H-Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-NH2, and its D-Met (O)2-analog were synthesized. In addition, analogs of [Arg6, Phe7] enkephalin substituted at the 2nd position by D-Ala and D-Met (O) were also synthesized, together with four other enkephalin analogs. Among these compounds, [D-Met (O)2] adrenorphin exhibited high analgesic activity (29.1 times that of morphine) antagonized by naloxone, when administered intracisternally to mice.

  合成了肾上腺肽（Adrenorphin）、H-Tyr-Gly-Gly-Phe-Met-Arg-Arg-Val-NH2及其D-Met (O)2类似物。此外，还合成了在第二位用D-Ala和D-Met (O)替代的[Arg6, Phe7]内啡肽的类似物，以及其他四种内啡肽类似物。在这些化合物中，[D-Met (O)2]肾上腺肽在小鼠颅内施用时表现出较高的镇痛活性（为吗啡的29.1倍），且其效应被纳洛酮拮抗。
• 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