H-Val-Gly-OBzl*TFA | 74939-29-0

• 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-Val-Gly-OBzl*TFA
• 英文别名: benzyl 2-[[(2S)-2-amino-3-methylbutanoyl]amino]acetate;2,2,2-trifluoroacetic acid
• CAS: 74939-29-0
• 化学式: C₂HF₃O₂*C₁₄H₂₀N₂O₃
• 分子量: 378.348
• InChiKey: NMGLKIBKBIHTQE-ZOWNYOTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  118.72
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  H-Val-Gly-OBzl*TFA 在 吡啶 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Solution phase synthesis and purification of the minigramicidin ion channels and a succinyl-linked gramicidin

  摘要：

  Peptides with alternating D- and L-configured residues as found in the natural ion channel active peptide gramicidin A (gA) are important building blocks for artificially engineered ion channels. We detail an optimised solution phase synthesis employing a convergent assembly of peptide building blocks, giving access to the minigramicidines and a succinyl linked gA derivative on preparative scale. Moreover, the minigramicidines were investigated for secondary structure formation by CD-spectroscopy. which was discovered to be medium and capping-group dependent. A parallel, left-handed double-beta-helix seems to be generally favoured in organic solvents for the minigramicidines. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00179-5
• 作为产物：
  描述：

  甘氨酸苄酯盐酸盐 在 N,N'-二环己基碳二亚胺 作用下， 生成 H-Val-Gly-OBzl*TFA
  参考文献：
  名称：

  A Synthesis of Human Proinsulin C-Peptide

  摘要：

  一段对应于人类前胰岛素C肽（前胰岛素分子中的第33至63位氨基酸序列）的三十一个氨基酸序列的多肽通过固相法被合成。产物依次通过凝胶过滤、DEAE-纤维素色谱法和高性能液相色谱法（HPLC）进行纯化。纯化后的物质在反相HPLC中表现为单一组分，呈现出正确的氨基酸比例，并且在免疫反应性和色谱行为上与天然人C肽无法区分。关于与HF切割相关可能发生的Asp-Leu序列上的α→β转肽反应，通过模型肽的研究表明，无论β-羧酸是自由状态还是被保护为苄酯状态，β-肽的形成率都为3-4%。

  DOI：

  10.1246/bcsj.54.3088

文献信息

• Amino acids and peptides. XXVIII. Synthesis of peptide fragments related to eglin c and studies on the relationship between their structure and effects on human leukocyte elastase, cathepsin G and .ALPHA.-chymotrypsin.
  作者：Satoshi TSUBOI、Kazunori NAKABAYASHI、Yoshikazu MATSUMOTO、Naoki TENO、Yuko TSUDA、Yoshio OKADA、Yoko NAGAMATSU、Junichiro YAMAMOTO

  DOI：10.1248/cpb.38.2369

  日期：——

  Various peptide fragments related to eglin c, which consists of 70 amino acid residues, were synthesized by a conventional solution method and their inhibitory effects on leukocyte elastase, cathepsin G and α-chymotrypsin were examined. Among them, H-Arg-Glu-Tyr-Phe-OMe (eglin c 22-25) and H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe (eglin c 41-49) inhibited cathepsin G and α-chymotrypsin but not leukocyte elastase, while H-Thr-Asn-Val-Val-OMe (eglin c 60-63) inhibited leukocyte elastase but not cathepsin G or α-chymotrypsin, although eglin c potently inhibited leukocyte elastase, cathepsin G and α-chymotrypsin. These results indicated that the interaction sites of eglin c with leukocyte elastase, cathepsin G and α-chymotrypsin might be different.

  采用常规的溶液法合成了与来自家蚕血淋巴的抗蛋白酶eglin c（由70个氨基酸残基构成）相关的各种肽片段，并检验了它们对白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶的抑制效应。其中，H-Arg-Glu-Tyr-Phe-OMe（eglin c 22-25）和H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe（eglin c 41-49）能抑制组织蛋白酶G和α-胰凝乳蛋白酶，但不能抑制白细胞弹性蛋白酶，而H-Thr-Asn-Val-Val-OMe（eglin c 60-63）能抑制白细胞弹性蛋白酶，但不能抑制组织蛋白酶G或α-胰凝乳蛋白酶，尽管eglin c对白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶都具有强抑制作用。这些结果提示，eglin c与白细胞弹性蛋白酶、组织蛋白酶G和α-胰凝乳蛋白酶的相互作用部位可能各不相同。
• Synthesis of temperature-dependent elastin-like peptide-modified dendrimer for drug delivery
  作者：Chie Kojima、Kotaro Irie

  DOI：10.1002/bip.22276

  日期：2013.11

  to a dendrimer, named elastin-mimetic dendrimer. The elastin-mimetic dendrimer formed beta-turn structure by heating. The elastin-mimetic dendrimer exhibited the inverse phase transition, depending on pH and NaCl concentration in addition to temperature. The elastin-mimetic dendrimer could encapsulate a model drug, rose bengal, even though the complex stability was similar to the dendrimer without

  树状聚合物是具有独特结构的合成大分子，其是潜在的单分子药物载体和潜在的肽支架。弹性蛋白是细胞外基质的主要成分之一，也是对温度敏感的生物大分子。Val-Pro-Gly-Val-Gly重复序列（一种弹性蛋白样肽）已用于设计人工弹性蛋白分子。在这项研究中，我们通过将Ac-Val-Pro-Gly-Val-Gly与树状大分子缀合，合成了一种新型的温度依赖性药物载体，该树状大分子被称为弹性蛋白模拟树状大分子。弹性蛋白模拟树状聚合物通过加热形成β-转角结构。模仿弹性体的树状聚合物除了温度外还取决于pH和NaCl浓度，表现出反相转变。弹性蛋白模拟树状大分子可以封装模型药物，玫瑰红，即使复合物的稳定性类似于没有弹性蛋白样肽的树状聚合物。因此，弹性蛋白模拟树状聚合物是具有温度和pH依赖性的潜在药物载体。（134字）（c）2013 Wiley Periodicals，Inc.生物聚合物（Pept Sci）100：714-721，2013。
• Fukuda, Tsunehiko; Wakimasu, Mitsuhiro; Kobayashi, Shigeru, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 8, p. 2825 - 2835
  作者：Fukuda, Tsunehiko、Wakimasu, Mitsuhiro、Kobayashi, Shigeru、Fujino, Masahiko

  DOI：——

  日期：——
• Syntheses and biological activities of bombesin analogs modified in the C-terminal dipeptide part
  作者：M Llinares、C Devin、J Azay、G Bergé、JA Fehrentz、J Martinez

  DOI：10.1016/s0223-5234(99)80063-4

  日期：1997.10

  Bombesin receptor antagonists are possible therapeutic agents due to their ability to act as inhibitors of cellular proliferation. On the basis of our hypothesis on the mechanism of action of gastrin associating an activating enzyme system to the receptor and on the results reported in the litterature, we have synthesized bombesin analogues which have been modified in the C-terminal Leu(13)-Leu(14) amide part. We have shown that modification in the C-terminal part of the bombesin strongly affected the biological activity in rat pancreatic acini. The most potent compound which is described here, H-D-Phe- Gln-Trp-Ala-Val-Gly-His-Leu-psi(CH2)Leu-NH2, was able to recognize the bombesin receptor on rat pancreatic acini (Ki 4.3 nM) and antagonized the bombesin stimulated amylase secretion (Ki 7.7 nM).
• Crystal structures of repeating peptides of elastin. 1. N-(tert-Butoxycarbonyl)-L-valyl-L-prolylglycyl-L-valylglycine
  作者：Hiroshi Ayato、Isao Tanaka、Tamaichi Ashida

  DOI：10.1021/ja00409a047

  日期：1981.9