2-O-methyl-L-glyceric acid | 1108702-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-methyl-L-glyceric acid
• 英文别名: (2S)-3-Hydroxy-2-methoxy-propanoic acid；(2S)-3-hydroxy-2-methoxypropanoic acid
• CAS: 1108702-39-1
• 化学式: C₄H₈O₄
• 分子量: 120.105
• InChiKey: YNLNJDRLOAQMFQ-VKHMYHEASA-N

物化性质

• 沸点：
  310.2±27.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-O-methyl-L-glyceric acid 、 2,4'-二溴苯乙酮 在 potassium hydrogencarbonate 、 18-冠醚-6 作用下， 以 水 、 乙腈 为溶剂， 生成 2-O-methyl-L-glyceric acid p-bromophenacyl ester
  参考文献：
  名称：

  Homotyrosine-Containing Cyanopeptolins 880 and 960 and Anabaenopeptins 908 and 915 from Planktothrix agardhii CYA 126/8

  摘要：

  Two homotyrosine-bearing cyanopeptolins are described from Planktothrix agardhii CYA 126/8. The compounds feature a common homotyrosine-containing cyclohexadepsipeptide and differ by sulfation of an exocyclically located 2-O-methyl-D-glyceric acid residue. In addition we describe two anabaenopeptins, which contain two homotyrosine residues, one of which is N-methylated. The anabaenopeptins have a common cyclopentapeptide portion and differ in the amino acid linked to it via an ureido bond, arginine and tyrosine, respectively.

  DOI：

  10.1021/np800557m
• 作为产物：
  描述：

  甲醇 、 L-丝氨酸 在 magnesium sulfate 、 溶剂黄146 、 亚硝酸异戊酯 作用下， 反应 4.0h， 生成 2-O-methyl-L-glyceric acid
  参考文献：
  名称：

  Jizanpeptins, Cyanobacterial Protease Inhibitors from a Symploca sp. Cyanobacterium Collected in the Red Sea

  摘要：

  Jizanpeptins A-E (1-5) are micropeptin depsipeptides isolated from a Red Sea specimen of a Symploca sp. cyanobacterium. The planar structures of the jizanpeptins were established using NMR spectroscopy and mass spectrometry and contain 3-amino-6-hydroxy-2-piperidone (Ahp) as one of eight residues in a typical micropeptin motif, as well as a side chain terminal glyceric acid sulfate moiety. The absolute configurations of the jizanpeptins were assigned using a combination of Marfey's methodology and chiral-phase HPLC analysis of hydrolysis products compared to commercial and synthesized standards. Jizanpeptins A-E showed specific inhibition of the serine protease trypsin (IC50 = 72 nM to 1 mu M) compared to chymotrypsin (IC50 = 1.4 to >10 mu M) in vitro and were not overtly cytotoxic to HeLa cervical or NCI-H460 lung cancer cell lines at micromolar concentrations.

  DOI：

  10.1021/acs.jnatprod.8b00117

文献信息

• Homotyrosine-Containing Cyanopeptolins 880 and 960 and Anabaenopeptins 908 and 915 from <i>Planktothrix agardhii</i> CYA 126/8
  作者：Hilary S. Okumura、Benjamin Philmus、Cyril Portmann、Thomas K. Hemscheidt

  DOI：10.1021/np800557m

  日期：2009.1.23

  Two homotyrosine-bearing cyanopeptolins are described from Planktothrix agardhii CYA 126/8. The compounds feature a common homotyrosine-containing cyclohexadepsipeptide and differ by sulfation of an exocyclically located 2-O-methyl-D-glyceric acid residue. In addition we describe two anabaenopeptins, which contain two homotyrosine residues, one of which is N-methylated. The anabaenopeptins have a common cyclopentapeptide portion and differ in the amino acid linked to it via an ureido bond, arginine and tyrosine, respectively.
• Jizanpeptins, Cyanobacterial Protease Inhibitors from a <i>Symploca</i> sp. Cyanobacterium Collected in the Red Sea
  作者：David A. Gallegos、Josep Saurí、Ryan D. Cohen、Xuemei Wan、Patrick Videau、Alec O. Vallota-Eastman、Lamiaa A. Shaala、Diaa T. A. Youssef、R. Thomas Williamson、Gary E. Martin、Benjamin Philmus、Aleksandra E. Sikora、Jane E. Ishmael、Kerry L. McPhail

  DOI：10.1021/acs.jnatprod.8b00117

  日期：2018.6.22

  Jizanpeptins A-E (1-5) are micropeptin depsipeptides isolated from a Red Sea specimen of a Symploca sp. cyanobacterium. The planar structures of the jizanpeptins were established using NMR spectroscopy and mass spectrometry and contain 3-amino-6-hydroxy-2-piperidone (Ahp) as one of eight residues in a typical micropeptin motif, as well as a side chain terminal glyceric acid sulfate moiety. The absolute configurations of the jizanpeptins were assigned using a combination of Marfey's methodology and chiral-phase HPLC analysis of hydrolysis products compared to commercial and synthesized standards. Jizanpeptins A-E showed specific inhibition of the serine protease trypsin (IC50 = 72 nM to 1 mu M) compared to chymotrypsin (IC50 = 1.4 to >10 mu M) in vitro and were not overtly cytotoxic to HeLa cervical or NCI-H460 lung cancer cell lines at micromolar concentrations.