Arg-Gly-Asp-Cys-S-[[1-[2-[(β-D-galactopyranosyl)oxy]ethyl]-1H-1,2,3-triazol-4-yl]methyl] | 1262387-89-2

• 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: Arg-Gly-Asp-Cys-S-[[1-[2-[(β-D-galactopyranosyl)oxy]ethyl]-1H-1,2,3-triazol-4-yl]methyl]
• 英文别名: (3S)-3-[[2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]acetyl]amino]-4-[[(1R)-1-carboxy-2-[[1-[2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]triazol-4-yl]methylsulfanyl]ethyl]amino]-4-oxobutanoic acid
• CAS: 1262387-89-2
• 化学式: C₂₆H₄₄N₁₀O₁₃S
• 分子量: 736.761
• InChiKey: QRHAKFIOAWDJIR-KNLCAOPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  50
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  408
• 氢给体数：
  12
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 copper diacetate 、 sodium ascorbate 作用下， 以 水 为溶剂， 反应 1.0h， 生成 Arg-Gly-Asp-Cys-S-[[1-[2-[(β-D-galactopyranosyl)oxy]ethyl]-1H-1,2,3-triazol-4-yl]methyl]
  参考文献：
  名称：

  Neoglycopeptides through direct functionalization of cysteine

  摘要：

  Neoglycopeptides are readily prepared by direct functionalization of cysteine-containing peptides followed by click triazole formation between the resulting propargylated peptides and protected or free (2-azido)-ethyl gluco-, manno,- and galactopyranosides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.021

文献信息

• ‘Click’ glycosylation of peptides through cysteine propargylation and CuAAC
  作者：Sandrine Lamandé-Langle、Charlotte Collet、Raphaël Hensienne、Christine Vala、Françoise Chrétien、Yves Chapleur、Amel Mohamadi、Patrick Lacolley、Véronique Regnault

  DOI：10.1016/j.bmc.2014.09.056

  日期：2014.12

  'Click' glycosylation of cysteine-containing peptides were carried out in good yield by Copper(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC). For that peptides were functionalized though direct propargylation of the cysteine residue allowing their use in CuAAC with suitable free or protected azido sugars of gluco, manno and galacto configuration. Among these free and protected glycopeptides a series of 'glycoRGD' peptides were obtained and submitted to in vitro platelet aggregation tests, showing that the pseudoglycosylation of the adhesion sequence lowers the IC50 value and thus could improve the in vivo pharmacokinetic properties. (C) 2014 Elsevier Ltd. All rights reserved.

  半胱氨酸肽通过Cu(I)催化的叠氮化物-炔烃环加成(CuAAC)实现了"点击"糖基化，产率良好。此方法中，肽通过半胱氨酸残基的直接炔基化进行官能化，使其可用于与具有gluco、manno和galacto构型的合适叠氮化糖（自由或保护状态）进行CuAAC反应。在所获得的自由和保护型糖肽中，一系列"glycoRGD"肽被制备并进行了体外血小板聚集测试，结果显示伪糖基化的黏附序列降低了IC50值，从而可能改善体内药代动力学特性。©2014 Elsevier Ltd. 保留所有权利。
• Neoglycopeptides through direct functionalization of cysteine
  作者：Christine Vala、Françoise Chrétien、Eva Balentova、Sandrine Lamandé-Langle、Yves Chapleur

  DOI：10.1016/j.tetlet.2010.10.021

  日期：2011.1

  Neoglycopeptides are readily prepared by direct functionalization of cysteine-containing peptides followed by click triazole formation between the resulting propargylated peptides and protected or free (2-azido)-ethyl gluco-, manno,- and galactopyranosides. (C) 2010 Elsevier Ltd. All rights reserved.