methyl-2,3-dihydroxy-3-methylbutyrate | 75347-92-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl-2,3-dihydroxy-3-methylbutyrate
• 英文别名: (S)-α,β-dihydroxyisovaleric methyl ester；methyl (2S)-2,3-dihydroxy-3-methylbutanoate
• CAS: 75347-92-1
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: GHWRZRNYIIZFRP-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,3-二甲基丙烯酸甲酯 在 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 生成 methyl-2,3-dihydroxy-3-methylbutyrate
  参考文献：
  名称：

  Serinolamides and Lyngbyabellins from an Okeania sp. Cyanobacterium Collected from the Red Sea

  摘要：

  NMR-and MS-guided fractionation of an extract of an Okeania sp. marine cyanobacterium, collected from the Red Sea, led to the isolation of four new metabolites, including serinolamides C (1) and D (2) and lyngbyabellins O (3) and P (4), together with the three known substances lyngbyabellins F (5) and G (6) and dolastatin 16 (7). The planar structures of the new compounds were determined using NMR and MS analyses. The absolute configurations of 1 and 2 were determined by Marfey's analysis of their hydrolysates. The absolute configuration of 3 was ascertained by chiral-phase chromatography of degradation products, while that of 4 was determined by comparison to 3 and 5. The cytotoxic and antifouling activities of these compounds were evaluated using MCF7 breast cancer cells and Amphibalanus amphitrite larvae, respectively. Compounds 3, 4, and 7 exhibited strong antifouling activity, and 3 and 7 were not cytotoxic. A structure-activity relationship was observed for the cytotoxicity of the lyngbyabellins with the presence of a side chain (4 is more active than 3) leading to greater activity. For the antifouling activity, the acyclic form without a side chain (3) was the most active.

  DOI：

  10.1021/acs.jnatprod.7b00449

文献信息

• Microbiological preparation of (S)-(+)-2,3-dihydroxy-3-methylbutanoic acid by syn dihydroxylation of 3-methylcrotonic acid
  作者：D. John Aberhart

  DOI：10.1021/jo01313a045

  日期：1980.12
• Serinolamides and Lyngbyabellins from an <i>Okeania</i> sp. Cyanobacterium Collected from the Red Sea
  作者：Julie G. Petitbois、Loida O. Casalme、Julius Adam V. Lopez、Walied M. Alarif、Ahmed Abdel-Lateff、Sultan S. Al-Lihaibi、Erina Yoshimura、Yasuyuki Nogata、Taiki Umezawa、Fuyuhiko Matsuda、Tatsufumi Okino

  DOI：10.1021/acs.jnatprod.7b00449

  日期：2017.10.27

  NMR-and MS-guided fractionation of an extract of an Okeania sp. marine cyanobacterium, collected from the Red Sea, led to the isolation of four new metabolites, including serinolamides C (1) and D (2) and lyngbyabellins O (3) and P (4), together with the three known substances lyngbyabellins F (5) and G (6) and dolastatin 16 (7). The planar structures of the new compounds were determined using NMR and MS analyses. The absolute configurations of 1 and 2 were determined by Marfey's analysis of their hydrolysates. The absolute configuration of 3 was ascertained by chiral-phase chromatography of degradation products, while that of 4 was determined by comparison to 3 and 5. The cytotoxic and antifouling activities of these compounds were evaluated using MCF7 breast cancer cells and Amphibalanus amphitrite larvae, respectively. Compounds 3, 4, and 7 exhibited strong antifouling activity, and 3 and 7 were not cytotoxic. A structure-activity relationship was observed for the cytotoxicity of the lyngbyabellins with the presence of a side chain (4 is more active than 3) leading to greater activity. For the antifouling activity, the acyclic form without a side chain (3) was the most active.