N-[(苄氧基)羰基]甘氨酰-L-脯氨酰-L-亮氨酸 | 2646-63-1

• 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
• 中文名称: N-[(苄氧基)羰基]甘氨酰-L-脯氨酰-L-亮氨酸
• 英文名称: N-[1-(N-benzyloxycarbonyl-glycyl)-L-prolyl]-L-leucine
• 英文别名: N-[1-(N-Benzyloxycarbonyl-glycyl)-L-prolyl]-L-leucin；Z-Gly-Pro-Leu；(2S)-4-methyl-2-[[(2S)-1-[2-(phenylmethoxycarbonylamino)acetyl]pyrrolidine-2-carbonyl]amino]pentanoic acid
• CAS: 2646-63-1
• 化学式: C₂₁H₂₉N₃O₆
• 分子量: 419.478
• InChiKey: QYDFKWAKGMDHJL-IRXDYDNUSA-N

物化性质

• 熔点：
  201-202 °C(Solv: water (7732-18-5); methanol (67-56-1))
• 沸点：
  714.2±60.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.523
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(苄氧基)羰基]甘氨酰-L-脯氨酰-L-亮氨酸 在 甲醇 、 palladium on activated charcoal 、 溶剂黄146 作用下， 生成 Gly-Pro-Leu
  参考文献：
  名称：

  Synthesis of Poly-(L-prolyl-L-leucyl-glycyl). An Attempted Synthesis of Model Collagen

  摘要：

  合成了两种三肽--l-脯氨酰-亮氨酰甘氨酸（IV）和甘氨酰-l-脯氨酰-亮氨酸（X），并用焦磷酸四乙酯法、碳化二亚胺法和对硝基苯硫酯法对 IV 进行了聚合，其中焦磷酸法的聚合效果最好。得到的多肽的最高分子量约为 6000，通过末端基团的测定，证实了多肽中原有三肽单元的重复。用焦磷酸四乙酯法对 IV 和 X 两种三肽的缩聚反应进行了平行比较，结果表明，IV 比 X 的产率更高、分子量更大。

  DOI：

  10.1246/bcsj.31.802
• 作为产物：
  描述：

  Z-甘氨酸-脯氨酸 在 异戊酰氯 作用下， 生成 N-[(苄氧基)羰基]甘氨酰-L-脯氨酰-L-亮氨酸
  参考文献：
  名称：

  Synthesis of Poly-(L-prolyl-L-leucyl-glycyl). An Attempted Synthesis of Model Collagen

  摘要：

  合成了两种三肽--l-脯氨酰-亮氨酰甘氨酸（IV）和甘氨酰-l-脯氨酰-亮氨酸（X），并用焦磷酸四乙酯法、碳化二亚胺法和对硝基苯硫酯法对 IV 进行了聚合，其中焦磷酸法的聚合效果最好。得到的多肽的最高分子量约为 6000，通过末端基团的测定，证实了多肽中原有三肽单元的重复。用焦磷酸四乙酯法对 IV 和 X 两种三肽的缩聚反应进行了平行比较，结果表明，IV 比 X 的产率更高、分子量更大。

  DOI：

  10.1246/bcsj.31.802

文献信息

• Action on peptides by wheat carboxypeptidase
  作者：H. Umetsu、E. Ichishima

  DOI：10.1016/0031-9422(83)83054-4

  日期：1983.1

  Abstract A kinetic analysis has been performed with purified wheat carboxypeptidase by the use of N -acyl dipeptides, Z-Gly-Pro-Leu-Gly (Z = benzyloxycarbonyl), angiotensin II and bradykinin. The values of k cat were dramatically influenced by amino acid residues occupying the penultimate position from the carboxyl terminus of substrates. The structure of the substrate did not appreciably affect the

  摘要 使用 N-酰基二肽、Z-Gly-Pro-Leu-Gly（Z = 苄氧羰基）、血管紧张素 II 和缓激肽对纯化的小麦羧肽酶进行了动力学分析。k cat 的值受到占据底物羧基末端倒数第二个位置的氨基酸残基的显着影响。底物的结构对 K m 值没有明显影响。
• Affinity chromatography of alkaline proteinase S on N-carbobenzoxyglycylleucylaminohexyl-Sepharose.
  作者：YOSHIO INOUYE、SHOSHIRO NAKAMURA、MASA HAMADA、KAZUO AIKAWA、KANSHIRO KITAGAKI、KAZUNORI SATO、EIICHI YASUDA

  DOI：10.1248/cpb.32.4036

  日期：——

  Alkaline proteinase produced by one of the monospore isolates of Streptomyces violaceorectus MC675-A8, a producer of the alkaline metalloendopeptidases named alkinonases A and AF, was purified by affinity chromatography on N-benzyloxycarbonylglycylleucylaminohexyl-Sepharose to electrophoretic homogeneity. The enzyme was inactivated by phenylmethanesulfonyl fluoride and diisopropylfluorophosphate, but not by chelating agents or sulfhydryl reagents, and was distinct from alkinonases A and AF. The optimum pH for casein hydrolysis was 9.5-10.5, and the enzyme was stable within a pH range of 5.0-12.0. The molecular weight was estimated to be 30000. The peptidase activity of the enzyme was greatest on N-benzyloxycarbonylglycylprolylleucylglycine ethyl ester among the synthetic substrates tested in this work. Amidase activity was observed towards peptide amides such as N-benzyloxycarbonylglycylleucine amide and N-benzyloxycarbonylglycylphenylalanine amide. The enzyme showed anti-inflammatory activity against carrageenan-induced edema in rats, as did alkinonases A and AF. Bradykinin was hydrolyzed by the enzyme to arginylprolylprolylglycylphenylalanylserylprolylphenylalanine and arginine. Since the enzyme showed a serine proteinase nature, the enzyme was named alkaline proteinase S, and the producing microbe was designated as Streptomyces violaceorectus MC675-A8-S.

  紫色直肠链霉菌 MC675-A8 的单孢子分离株之一产生的碱性蛋白酶，它是名为阿激酶 A 和 AF 的碱金属内肽酶的生产者，通过 N-苄氧基羰基甘氨酰氨基己基-琼脂糖凝胶上的亲和层析纯化至电泳均质。该酶可被苯甲磺酰氟和二异丙基氟磷酸酯灭活，但不会被螯合剂或巯基试剂灭活，并且与羟激酶 A 和 AF 不同。酪蛋白水解的最适pH为9.5-10.5，酶在pH 5.0-12.0范围内稳定。分子量估计为30000。在本工作测试的合成底物中，该酶对N-苄氧基羰基甘氨酰脯氨酰甘氨酸乙酯的肽酶活性最大。观察到针对肽酰胺例如N-苄氧基羰基甘氨酰亮氨酸酰胺和N-苄氧基羰基甘氨酰苯丙氨酸酰胺的酰胺酶活性。该酶对角叉菜胶引起的大鼠水肿具有抗炎活性，羟激酶 A 和 AF 也具有同样的效果。缓激肽被酶水解成精氨酰脯氨酰甘氨酰苯丙氨酰丝氨酰脯氨酰苯丙氨酸和精氨酸。由于该酶显示出丝氨酸蛋白酶性质，因此将该酶命名为碱性蛋白酶S，并且将产生微生物命名为Streptomyces violaceorectus MC675-A8-S。
• Synthesis of Poly-(L-prolyl-L-leucyl-glycyl). An Attempted Synthesis of Model Collagen
  作者：Hidetoshi Kitaoka、Shumpei Sakakibara、Hisaya Tani

  DOI：10.1246/bcsj.31.802

  日期：1958.7

  The two tripeptides, l-prolyl-l-leucylglycine (IV) and glycyl-l-prolyl-l-leucine (X), were synthesized, and IV was subjected to polymerization by the tetraethyl pyrophosphite, carbodiimide and p-nitrophenyl thioester methods, in which the most promising result was obtained by the pyrophosphite method. The highest molecular weight of the polypeptide which was obtained was about 6000 and the repetition of the original tripeptide unit in the polypeptide was confirmed by the end groups determination. The polycondensation reactions of both the tripeptides, IV and X, were compared in parallel runs by the tetraethyl pyrophosphite procedure, and the comparison showed that IV gave a better yield and a higher molecular weight product than X. X and poly-(l-prolyl-l-leucyl-glycyl), which was obtained from IV, contained firmly bound water in spite of the fact that IV contained no crystallization water.

  合成了两种三肽--l-脯氨酰-亮氨酰甘氨酸（IV）和甘氨酰-l-脯氨酰-亮氨酸（X），并用焦磷酸四乙酯法、碳化二亚胺法和对硝基苯硫酯法对 IV 进行了聚合，其中焦磷酸法的聚合效果最好。得到的多肽的最高分子量约为 6000，通过末端基团的测定，证实了多肽中原有三肽单元的重复。用焦磷酸四乙酯法对 IV 和 X 两种三肽的缩聚反应进行了平行比较，结果表明，IV 比 X 的产率更高、分子量更大。