H-Gly-Asp(OMe)-OMe hydrochloride | 138403-48-2

• 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-Gly-Asp(OMe)-OMe hydrochloride
• 英文别名: Gly-Asp(OMe)-OMe*HCl；Gly-L-Asp(OCH3)2*HCl；dimethyl (2S)-2-[(2-aminoacetyl)amino]butanedioate;hydrochloride
• CAS: 138403-48-2
• 化学式: C₈H₁₅N₂O₅*Cl
• 分子量: 254.671
• InChiKey: QWTTXUGDBNFLRZ-JEDNCBNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.41
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  107.72
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  H-Gly-Asp(OMe)-OMe hydrochloride 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 Boc-Arg-Gly-Asp-OH
  参考文献：
  名称：

  The structure-antiaggregative activity relationship in a series of Arg-Gly-Asp analogues

  摘要：

  A series of analogues of Arg-Gly-Asp tripeptide, the common structural element of most of the integrin receptor ligands, possessing different conformational features for the interaction with platelet receptors, were synthesized by the methods of conventional peptide chemistry for use in the search for antithrombotic agents. The distance between the guanidine group of Arg and the beta-carboxyl group of Asp was shown to affect the antia-regative activity. A potent inhibitor of platelet aggregation, tripeptide Arg-beta Ala-Asp, with IC50 10.6 = 10.6 mu M (ADP, 1.5 gM) was revealed.

  DOI：

  10.1134/s1068162006020038
• 作为产物：
  描述：

  L-天冬氨酸二甲酯盐酸盐 在 盐酸 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 H-Gly-Asp(OMe)-OMe hydrochloride
  参考文献：
  名称：

  The structure-antiaggregative activity relationship in a series of Arg-Gly-Asp analogues

  摘要：

  A series of analogues of Arg-Gly-Asp tripeptide, the common structural element of most of the integrin receptor ligands, possessing different conformational features for the interaction with platelet receptors, were synthesized by the methods of conventional peptide chemistry for use in the search for antithrombotic agents. The distance between the guanidine group of Arg and the beta-carboxyl group of Asp was shown to affect the antia-regative activity. A potent inhibitor of platelet aggregation, tripeptide Arg-beta Ala-Asp, with IC50 10.6 = 10.6 mu M (ADP, 1.5 gM) was revealed.

  DOI：

  10.1134/s1068162006020038

文献信息

• Cyclotetrapeptide Complexes of Nickel( <scp>II</scp> ) and Palladium( <scp>II</scp> ) by Template Synthesis from Dipeptide Esters with Functionalized Side Chains − Crystal Structure of [( <i>cyclo</i> ‐Gly‐β‐Ala‐Gly‐β‐Ala‐4H ⁺ )Cu](PPN) ₂
  作者：Jan Schapp、Katharina Haas、Karlheinz Sünkel、Wolfgang Beck

  DOI：10.1002/ejic.200300067

  日期：2003.10

  The cyclocondensations of dipeptide esters [Gly-L-Asp(OMe)2, Gly-L-Glu(OMe)2, L-AspOMe-β-AlaOMe, β-Ala-L-Lys(ψ-N-Boc,OMe), β-Ala-L-Orn(ψ-N-Boc,OMe)] at nickel(II), palladium(II), and copper(II) templates give dianionic square-planar complexes of deprotonated cyclotetrapeptides that contain functional groups in the side chains. The complexes with 14- or 16-membered rings were isolated as [Ph3PNPPh3]+

  二肽酯的环缩合反应 [Gly-L-Asp(OMe)2, Gly-L-Glu(OMe)2, L-AspOMe-β-AlaOMe, β-Ala-L-Lys(ψ-N-Boc,OMe) , β-Ala-L-Orn(ψ-N-Boc,OMe)] 在镍 (II)、钯 (II) 和铜 (II) 模板上产生去质子化环四肽的双阴离子方形平面复合物，其中含有官能团侧链。具有 14 或 16 元环的复合物被分离为 [Ph3PNPPh3]+ 盐。[环-Gly-Asp(OMe)-Gly-Asp(OMe)-4H+]Pd}2-的水解得到四阴离子复合物[环-Gly-Asp(O-)-Gly-Asp(O-)- 4H+}Pd]4-(Li+)2(PNP+)2。还报道了[(环-Gly-β-Ala-Gly-β-Ala-4H+)Cu](PPN)2 的晶体结构。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451
• Syntheses and in vitro antitumor activities of ferrocene-conjugated Arg-Gly-Asp peptides
  作者：Binbin Zhou、Juan Li、Bi-Jun Feng、Yang Ouyang、You-Nian Liu、Feimeng Zhou

  DOI：10.1016/j.jinorgbio.2012.06.014

  日期：2012.11

  Ferrocene (Fc) and its conjugates have attracted considerable attention in recent years due to their unique electrochemical behavior and significant biological activities such as antitumor, antimalarial, and antifungal. Arg-Gly-Asp (RGD)-containing peptides, because of their selective binding to integrins which are highly expressed in tumor-induced angiogenesis, play a key role in cancer targeted therapy. In this study. Fc-RGD and Fc-Am-RGD (Fc: ferrocenoyl; Am: 6-aminohexanoic acid) conjugates were synthesized, and the antitumor activities in vitro were investigated. The cell uptake of the conjugates by B16 murine melanoma cells was measured using HPLC-electrochemical method. The antitumor activities of the conjugates were also evaluated by 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) and flow cytometric measurements. The experimental results revealed that Fc-RGD and Fc-Am-RGD exhibit more effective antitumor activities than their parent compounds RGD and Fc-COOH. Moreover, it is found that Fc-Am-RGD yields the lowest IC50 values of 5.2 +/- 1.4 mu M toward B16 cells. The HPLC-electrochemical studies confirmed that the insertion of flexible alkyl spacer Am between Fc and RGD significantly increases the cell uptake toward B16 cells and consequently improves the antitumor activity. Our results suggest that Fc-RGD and Fc-Am-RGD conjugates are potential candidates for cancer treatment. (c) 2012 Elsevier Inc. All rights reserved.
• Bis(dipeptide ester–H+) Complexes of Palladium(II) – Precursors for the Formation of Cyclotetrapeptides
  作者：Katharina Haas、Eva-Maria Ehrenstorfer-Schäfers、Kurt Polborn、Wolfgang Beck

  DOI：10.1002/(sici)1099-0682(199903)1999:3<465::aid-ejic465>3.0.co;2-5

  日期：1999.3
• Synthesis of glycopeptide derivatives of glycyrrhizinic acid and their immunomodulatory properties
  作者：L. A. Baltina、G. M. Sakhautdinova、F. Z. Zarudii、D. N. Lazareva、G. A. Tolstikov、V. A. Davydova

  DOI：10.1007/bf00766858

  日期：1990.2
• The structure-antiaggregative activity relationship in a series of Arg-Gly-Asp analogues
  作者：O. V. Mel’nik、V. P. Martinovich、V. P. Golubovich

  DOI：10.1134/s1068162006020038

  日期：2006.3

  A series of analogues of Arg-Gly-Asp tripeptide, the common structural element of most of the integrin receptor ligands, possessing different conformational features for the interaction with platelet receptors, were synthesized by the methods of conventional peptide chemistry for use in the search for antithrombotic agents. The distance between the guanidine group of Arg and the beta-carboxyl group of Asp was shown to affect the antia-regative activity. A potent inhibitor of platelet aggregation, tripeptide Arg-beta Ala-Asp, with IC50 10.6 = 10.6 mu M (ADP, 1.5 gM) was revealed.