(3S)-3-[[2-[[(2S)-2-氨基-5-(二氨基亚甲基氨基)戊酰]氨基]乙酰基]氨基]-4-[[(2S)-1-羟基-1-氧代-3-苯基丙烷-2-基]氨基]-4-氧代丁酸 | 110697-46-6

• 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: (3S)-3-[[2-[[(2S)-2-氨基-5-(二氨基亚甲基氨基)戊酰]氨基]乙酰基]氨基]-4-[[(2S)-1-羟基-1-氧代-3-苯基丙烷-2-基]氨基]-4-氧代丁酸
• 英文名称: H-Arg-Gly-Asp-Phe-OH
• 英文别名: Arg-Gly-Asp-Phe；RGDF；H - Arg - Gly - Asp - Phe - OH；Arginyl-glycyl-aspartyl-phenylalanine；(3S)-3-[[2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]acetyl]amino]-4-[[(1S)-1-carboxy-2-phenylethyl]amino]-4-oxobutanoic acid
• CAS: 110697-46-6
• 化学式: C₂₁H₃₁N₇O₇
• 分子量: 493.52
• InChiKey: ARNGIGOPGOEJCH-KKUMJFAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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 、 (3S)-3-[[2-[[(2S)-2-氨基-5-(二氨基亚甲基氨基)戊酰]氨基]乙酰基]氨基]-4-[[(2S)-1-羟基-1-氧代-3-苯基丙烷-2-基]氨基]-4-氧代丁酸 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24%的产率得到(3S)-4-[[(1S)-1-carboxy-2-phenylethyl]amino]-3-[[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]-4-oxobutanoic 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：

  3-苯基-L-丙氨酸苄酯 在 N-甲基吗啉 、 盐酸 、 三氟甲磺酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 生成 (3S)-3-[[2-[[(2S)-2-氨基-5-(二氨基亚甲基氨基)戊酰]氨基]乙酰基]氨基]-4-[[(2S)-1-羟基-1-氧代-3-苯基丙烷-2-基]氨基]-4-氧代丁酸
  参考文献：
  名称：

  Poly-α,β-aspartyl-Arg-Gly-Asp-Phe: a novel polymeric nanomedicine

  摘要：

  一种新型纳米医学的高抗血栓效果、作用靶点和纳米结构被描述了。

  DOI：

  10.1039/c4md00331d

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：——
• 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.
• 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.
• Derivatives of N-amidinoproline and their use in conventional and solid phase peptide synthesis
  作者：S. V. Burov、Yu. E. Moskalenko、M. V. Leko、M. Yu. Dorosh、E. F. Panarin

  DOI：10.1134/s1068162006060021

  日期：2006.12

  N-Amidinoproline, a hybrid structure modeling key features of the Arg-Pro sequence, was synthesized. The activation of carboxyl group of free N-amidinoproline was found to result in the formation of a cyclic side product, whose structure was confirmed by ESI MS, H-1 NMR, and C-13 NMR spectra. The preparation of N-(mesitylenesulfonylatnidino)-L-proline using the mesitylenesulfonyl derivative of 2-methylisothiourea was demonstrated to be accompanied by partial racemization. The target product was synthesized by modification of N-amidinoproline by mesitylenesulfonyl chloride. The possibility of using N-amidinoproline in the N-terminal modification of a peptide chain was shown by the example of synthesis of an analogue of the 95-98 fragment of fibrinogen alpha chain.
• 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.