Fmoc-HN-Pro-Gly-OH | 250695-65-9

• 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: Fmoc-HN-Pro-Gly-OH
• 英文别名: Fmoc-Pro-Gly；Fmoc-Pro-Gly-OH；2-[[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]amino]acetic acid
• CAS: 250695-65-9
• 化学式: C₂₂H₂₂N₂O₅
• 分子量: 394.427
• InChiKey: YINDOSYVRZADBY-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-HN-Pro-Gly-OH 、 {(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-6-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-hexanoylamino}-acetic acid 在 三氟乙酸 作用下， 生成
  参考文献：
  名称：

  α-Galactose based neoglycopeptides. Inhibition of verotoxin binding to globotriosylceramide

  摘要：

  Solution and solid phase strategies for the synthesis of a-galactose based neoglycopeptide derivatives 2-13 were developed. Neoglycopeptides generated were tested for the inhibition of verotoxin binding to globotriosylceramide (Gb3) using ELISA. Among all of the compounds tested, only the lipid derivatives of neoglycopeptides, 11, 12 and 13 were found to be inhibitors, IC50 = 2.0 mM (11b and 12c) and 0.2 mM (11c and 13c). All of the inhibitors (11b, 11c, 12c and 13c) have a similar branching of the two alpha-galactosyl units at the N-terminal glycine residue of a short peptide and a lipid moiety attached at the C-terminal site. Both of these factors seem to be crucial for the inhibition. It is interesting to note that the inhibitors have only a portion of the natural trisaccharide ligand. The secondary groups either may contribute in sub-site oriented interactions with the protein receptors or may mimic the internal sugar units of the cell-surface ligand, Gb3. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00226-6
• 作为产物：
  描述：

  Fmoc-glycine-2-chlorotrityl resin 、 Fmoc-L-脯氨酸 在 哌啶 、 2-肟氰乙酸乙酯 、 N,N'-二异丙基碳二亚胺 、 三氟乙酸 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 1.27h， 以1.5 g的产率得到Fmoc-HN-Pro-Gly-OH
  参考文献：
  名称：

  在绿色固相肽合成中使用γ-戊内酯（GVL）时的故障排除

  摘要：

  使用固相策略可方便地进行用于研究和API生产的肽合成。但是，这种方法的主要缺点是需要大量的有害溶剂。在这方面，参加ACS绿色化学研究所药物圆桌会议的几个制药行业对识别用于固相肽合成的绿色溶剂表现出了浓厚的兴趣。在先前的研究中，我们小组提出了γ-戊内酯（GVL）替代危险DMF的建议。但是，在Fmoc去除受阻较少的Gly残基的过程中，可能会发生GVL的酰化反应。在这里，我们证明可以通过掺入带有Gly作为C端的相应二肽来规避这种副反应。这些二肽是使用CTC树脂方便地制备的，激活后可以重复使用。使用该策略，事实证明，在合成所需的包含五个Gly残基的ABRF 1992肽时，GVL略优于DMF。

  DOI：

  10.1021/acs.oprd.9b00073

文献信息

• α-Galactose based neoglycopeptides. Inhibition of verotoxin binding to globotriosylceramide
  作者：Prabhat Arya、Kristina M.K. Kutterer、Huiping Qin、Johanne Roby、Michael L. Barnes、Shuqiong Lin、Clifford A. Lingwood、Markus G. Peter

  DOI：10.1016/s0968-0896(99)00226-6

  日期：1999.12

  Solution and solid phase strategies for the synthesis of a-galactose based neoglycopeptide derivatives 2-13 were developed. Neoglycopeptides generated were tested for the inhibition of verotoxin binding to globotriosylceramide (Gb3) using ELISA. Among all of the compounds tested, only the lipid derivatives of neoglycopeptides, 11, 12 and 13 were found to be inhibitors, IC50 = 2.0 mM (11b and 12c) and 0.2 mM (11c and 13c). All of the inhibitors (11b, 11c, 12c and 13c) have a similar branching of the two alpha-galactosyl units at the N-terminal glycine residue of a short peptide and a lipid moiety attached at the C-terminal site. Both of these factors seem to be crucial for the inhibition. It is interesting to note that the inhibitors have only a portion of the natural trisaccharide ligand. The secondary groups either may contribute in sub-site oriented interactions with the protein receptors or may mimic the internal sugar units of the cell-surface ligand, Gb3. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Troubleshooting When Using γ-Valerolactone (GVL) in Green Solid-Phase Peptide Synthesis
  作者：Ashish Kumar、Adeniyi Thompson-Adewumi、K. P. Nandhini、Jonathan M. Collins、Fernando Albericio、Beatriz G. de la Torre

  DOI：10.1021/acs.oprd.9b00073

  日期：2019.5.17

  solid-phase peptide synthesis. In a previous study, our group proposed γ-valerolactone (GVL) as a replacement for the hazardous DMF. However, during Fmoc removal of the less hindered Gly residue, acylation with GVL can take place. Here we demonstrate that this side reaction can be circumvented by the incorporation of the corresponding dipeptides that carry Gly as the C-terminal. These dipeptides were conveniently

  使用固相策略可方便地进行用于研究和API生产的肽合成。但是，这种方法的主要缺点是需要大量的有害溶剂。在这方面，参加ACS绿色化学研究所药物圆桌会议的几个制药行业对识别用于固相肽合成的绿色溶剂表现出了浓厚的兴趣。在先前的研究中，我们小组提出了γ-戊内酯（GVL）替代危险DMF的建议。但是，在Fmoc去除受阻较少的Gly残基的过程中，可能会发生GVL的酰化反应。在这里，我们证明可以通过掺入带有Gly作为C端的相应二肽来规避这种副反应。这些二肽是使用CTC树脂方便地制备的，激活后可以重复使用。使用该策略，事实证明，在合成所需的包含五个Gly残基的ABRF 1992肽时，GVL略优于DMF。