Z-Pro-Leu-Gly-OH | 7801-38-9

• 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: Z-Pro-Leu-Gly-OH
• 英文别名: 2-[[(2S)-4-methyl-2-[[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]amino]pentanoyl]amino]acetic acid
• CAS: 7801-38-9
• 化学式: C₂₁H₂₉N₃O₆
• mdl: MFCD00057239
• 分子量: 419.478
• InChiKey: WOTUJALMKRAEDD-IRXDYDNUSA-N

物化性质

• 熔点：
  165.5-166 °C
• 沸点：
  715.3±60.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、乙醇（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：

  Z-Pro-Leu-Gly-OH 生成 Z-Pro-Leu-Gly-NHOH
  参考文献：
  名称：

  SPIBURG, CURTIS A.;MOORE, WILLIAM M.

  摘要：

  DOI：
• 作为产物：
  描述：

  benzoyloxycarbonylprolyl-leucyl-glycine amide 在 水 作用下， 生成 Z-Pro-Leu-Gly-OH
  参考文献：
  名称：

  Steinke, Doerte; Kula, Maria-Regina, Angewandte Chemie, 1990, vol. 102, # 10, p. 1204 - 1206

  摘要：

  DOI：

文献信息

• Substrate-Directed Lewis-Acid Catalysis for Peptide Synthesis
  作者：Wataru Muramatsu、Tomohiro Hattori、Hisashi Yamamoto

  DOI：10.1021/jacs.9b03850

  日期：2019.8.7

  A Lewis-acid-catalyzed method for the substrate-directed formation of peptide bonds has been developed, and this powerful approach is utilized for the new "remote" activation of carboxyl groups under solvent-free conditions. The presented method has the following advantages: 1) the high-yielding peptide synthesis uses a tantalum catalyst for any amino acids; 2) the reaction proceeds without any racemization;

  一种路易斯酸催化的底物定向形成肽键的方法已经被开发出来，这种强大的方法被用于在无溶剂条件下对羧基进行新的“远程”活化。该方法具有以下优点：1）高产肽合成对任何氨基酸均使用钽催化剂；2) 反应进行时没有任何外消旋化；3）采用钛催化剂的新型底物导向化学连接适用于会聚肽合成。这些优势克服了经典肽合成中一些未解决的问题。
• C-Terminal18F-fluoroethylamidation exemplified on [Gly-OH9] oxytocin
  作者：M. Jelinski、K. Hamacher、H. H. Coenen

  DOI：10.1002/jlcr.547

  日期：2002.3.15

  in presence of TBTU yielded ⩾90% of the 18F-fluoroethyl-amidated tripeptide. TBTU-mediated condensation of n.c.a. 2-[18F]fluoro-ethylamine with the C-terminal free acid group of protected oxytocin gave the radiochemical yield of about 75%. Deprotection under acidic conditions led to the formation of [Gly–(2-[18F]fluoroethyl)NH9]oxytocin within 75 min with a radiochemical yield of about 30% as measured

  受保护的九肽 Boc–Cys–Tyr(tBu)–Ile–Gln(Mtt)–Asn(Mtt)–Cys–Pro–Leu–Gly–OH 的酸功能的无载体添加 (nca) 18F-氟乙基酰胺化描述了形成标记的肽激素衍生物[Gly-(2-[18F]氟乙基)NH9]-催产素。使用与催产素 C 端序列相同的受保护三肽详细说明标记条件。辅基 nca 2-[18F] 氟乙胺是通过穴状化合物介导的 nca 18F-氟化在 DMSO（RCY：约 60%）中 N-Boc-2-（对甲苯磺酰氧基）乙胺和随后脱保护合成的，放射化学产率为46±5%。[18F]氟乙胺与Z-Pro-Leu-Gly-OH在偶联剂TBTU或模型三肽的活化酯存在下反应。活化酯方法以及在 TBTU 存在下的缩合产生⩾ 90% 的 18F-氟乙基酰胺化三肽。TBTU 介导的 nca 2-[18F] 氟-乙胺与受保护的催产素的 C 端游离酸基团的缩合得到约
• 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。
• Next Generation of Fluorometric Protease Assays: 7‐Nitrobenz‐2‐oxa‐1,3‐diazol‐4‐yl‐amides (NBD‐Amides) as Class‐Spanning Protease Substrates
  作者：Hannah Maus、Patrick Müller、Mergim Meta、Sabrina N. Hoba、Stefan J. Hammerschmidt、Robert A. Zimmermann、Collin Zimmer、Natalie Fuchs、Tanja Schirmeister、Fabian Barthels

  DOI：10.1002/chem.202301855

  日期：2023.9.6

  A game-changing generation of new protease assay substrates have been developed by using the nitrobenzofurazane (NBD) fluorophore. With applications across different protease classes, this breakthrough promises to decisively improve fluorometric assays in protease drug discovery.

  通过使用硝基苯并呋喃 (NBD) 荧光团，开发了新一代颠覆性的新型蛋白酶检测底物。通过跨不同蛋白酶类别的应用，这一突破有望决定性地改进蛋白酶药物发现中的荧光测定。
• Effect of changing the COOH-terminal amide group present in the hydrophilic cluster of oxytocin to dimethylamide
  作者：Yuan Fen Ting、Clark W. Smith、Glenn L. Stahl、Roderich Walter、Paul Cordopatis、Dimitrios Theodoropoulos

  DOI：10.1021/jm00180a026

  日期：1980.6

  Oxytocinoic acid dimethylamide was synthesized by stepwise solution techniques as part of an ongoing evaluation of the effects on the biological activity of oxytocin caused by individually changing the groups that comprises the hydrophilic surface of the hormone to more hydrophobic and more bulky groups. The analogue exhibited approximately 3% of the potency of oxytocin in the in vitro uterotonic assay. In addition, it possesses potencies of less than 0.07, less than 0.01, and 0.096 unit/mg in the avian vasodepressor, rat pressor, and rat antidiuretic assays, respectively. In the in vitro uterotonic assay, oxytocinoic acid dimethylamide showed a reduced affinity for the oxytocin receptor, a nonparallel dose-response relationship, and most importantly a reduced intrinsic activity as compared to oxytocin. The results suggest that the replacement of the protons of the primary carboxyamide of Gly9-NH2 of oxytocin by methyl groups displaces the active elements from the orientation for obtaining maximal intrinsic activity in the isolated rat uterus.