H-Arg-Gly-Asp-Val-OH | 93674-99-8

• 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-Arg-Gly-Asp-Val-OH
• 英文别名: arg-Gly-Asp-Val；RGDV；Arginyl-glycyl-aspartyl-valine；(2S)-2-[[(2S)-2-[[2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]acetyl]amino]-3-carboxypropanoyl]amino]-3-methylbutanoic acid
• CAS: 93674-99-8
• 化学式: C₁₇H₃₁N₇O₇
• 分子量: 445.476
• InChiKey: MDNRBNZIOBQHHK-KWBADKCTSA-N

物化性质

• 熔点：
  120-121 °C
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  252
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-O-(2,5-dioxopyrrolidin-1-yl) 1-O-[2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] butanedioate 、 H-Arg-Gly-Asp-Val-OH 在 N-甲基吗啉 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以26%的产率得到(2S)-2-[[(2S)-3-carboxy-2-[[2-[[(2S)-5-(diaminomethylideneamino)-2-[[4-[2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-4-oxobutanoyl]amino]pentanoyl]amino]acetyl]amino]propanoyl]amino]-3-methylbutanoic acid
  参考文献：
  名称：

  RGD-peptides modifying dexamethasone: to enhance the anti-inflammatory efficacy and limit the risk of osteoporosis

  摘要：

  RGD肽修饰地塞米松可以增强其抗炎效力并限制骨质疏松症的风险。

  DOI：

  10.1039/c5md00215j
• 作为产物：
  描述：

  L-缬氨酸苄酯 在 氢氟酸 作用下， 生成 H-Arg-Gly-Asp-Val-OH
  参考文献：
  名称：

  Dual-acting agents that possess free radical scavenging and antithrombotic activities: Design, synthesis, and evaluation of phenolic tetrahydro-β-carboline RGD peptide conjugates

  摘要：

  A new approach to construct a single dual-acting agent is described. Compounds 6a-c are potent free radical scavengers as demonstrated by the EC50 values in PC12 cell survival assay in term of NO, H2O2, and (OH)-O-. scavenging activity. The Ach-induced vaso-relaxation assay further confirms the potent NO scavenging activity of compounds 6a-c. In addition, 6a-c are efficacious in a rat arterial thrombosis, and are active in ADP- or PAF-induced in vitro platelet aggregation assay, suggesting that compounds 6a-c also possess anti-thrombotic activities. Since both free radical and thrombogenesis are important risk factors in myocardial ischemic/reperfusion injuries, these dual-acting agents having both free radical scavenging and antithrombolic activities may potentially be beneficial toward their treatment. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.024

文献信息

• Zhao, Ming; Peng, Shiqi, Advanced Synthesis and Catalysis, 1999, vol. 341, # 7, p. 668 - 676
  作者：Zhao, Ming、Peng, Shiqi

  DOI：——

  日期：——
• Improved Anti-Osteoporosis Potency and Reduced Endometrial Membrane Hyperplasia During Hormone Replacement Therapy with Estrogen−RGD Peptide Conjugates
  作者：Yu Xiong、Ming Zhao、Chao Wang、Heng Wei Chang、Shiqi Peng

  DOI：10.1021/jm070242a

  日期：2007.7.1

  To improve the specificity and potency of estrogen replacement therapy therapeutics while also minimizing the side effects such as bone resorption and thickening of the uterine wall, a series of novel estrogen-derived conjugates estradiol-3-RGD, estradiol-17-RGD, and estrone-3-RGD peptides have been prepared. In a mouse model, intraperitoneal (i.p.) administration of these estrogen-RGD peptide conjugates resulted in decreased serum concentrations of calcium and alkaline phosphatase, as well as increased levels of calcium, phosphorus, and minerals in the mouse femur. Furthermore, the anti-osteoporosis action of these conjugates followed a dose-dependent manner and was accompanied with no observable effects on endometrial cell hyperplasia. In addition to all of these compounds exhibiting biological activity when administered by the i.p. route, we were particularly pleased to note that the estradiol-3-RGD and estradiol-17-RGD conjugates were both orally active.
• Synthesis and antithrombotic activity of carbolinecarboxyl RGD sequence
  作者：Na Lin、Ming Zhao、Chao Wang、Shiqi Peng

  DOI：10.1016/s0960-894x(01)00809-5

  日期：2002.2

  3S-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid, RGDS, RGDV, RGDF and their linkers were synthesized. The anti-aggregation and adhesion of platelet indicated that the in vitro activities of the linkers remained at the same level as RGDS, RGDV, and RGDF (p > 0.05). The antithrombotic activities in vivo suggested, however, that the potencies of RGDS, RGDV and RGDF were enhanced by the introduction of 3S-1,2,3,4-tetrahydo-beta-carboline-3-carboxyl group into their alpha amino group (p < 0.05, 0.01 or 0.001). (C) 2002 Elsevier Science Ltd. All rights reserved.
• Dual-acting agents that possess free radical scavenging and antithrombotic activities: Design, synthesis, and evaluation of phenolic tetrahydro-β-carboline RGD peptide conjugates
  作者：Wei Bi、Lanrong Bi、Jianhui Cai、Sanguang Liu、Shiqi Peng、Nicholas O. Fischer、Jeffrey B.-H. Tok、Guohua Wang

  DOI：10.1016/j.bmcl.2006.06.024

  日期：2006.9

  A new approach to construct a single dual-acting agent is described. Compounds 6a-c are potent free radical scavengers as demonstrated by the EC50 values in PC12 cell survival assay in term of NO, H2O2, and (OH)-O-. scavenging activity. The Ach-induced vaso-relaxation assay further confirms the potent NO scavenging activity of compounds 6a-c. In addition, 6a-c are efficacious in a rat arterial thrombosis, and are active in ADP- or PAF-induced in vitro platelet aggregation assay, suggesting that compounds 6a-c also possess anti-thrombotic activities. Since both free radical and thrombogenesis are important risk factors in myocardial ischemic/reperfusion injuries, these dual-acting agents having both free radical scavenging and antithrombolic activities may potentially be beneficial toward their treatment. (c) 2006 Elsevier Ltd. All rights reserved.
• RGD-peptides modifying dexamethasone: to enhance the anti-inflammatory efficacy and limit the risk of osteoporosis
  作者：Hualong Yu、Shenghui Mei、Li Zhao、Ming Zhao、Yuji Wang、Haimei Zhu、Yaonan Wang、Jianhui Wu、Chunying Cui、Wenyun Xu、Shiqi Peng

  DOI：10.1039/c5md00215j

  日期：——

  RGD-peptides modifying dexamethasone can enhance the anti-inflammatory efficacy and limit the risk of osteoporosis.

  RGD肽修饰地塞米松可以增强其抗炎效力并限制骨质疏松症的风险。