sn-[3-2H1]-glycerol | 56065-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sn-[3-2H1]-glycerol
• 英文别名: L-<3-2H>-Glycerin；(1Ξ,2R)-1-deuterio-propane-1,2,3-triol；(2R)-1-deuteriopropane-1,2,3-triol
• CAS: 56065-27-1；125257-42-3；125257-50-3；139886-84-3；139886-85-4
• 化学式: C₃H₈O₃
• 分子量: 93.0868
• InChiKey: PEDCQBHIVMGVHV-VWLXYGTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.67
• 重原子数：
  6.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  月桂酰氯 、 sn-[3-2H1]-glycerol 在 吡啶 作用下， 生成 trilauroyl-sn-[3-2H1]-glycerol
  参考文献：
  名称：

  通过超高分辨率13C核磁共振测量脂肪酶催化酸解反应中的立体选择性

  摘要：

  AbstractElucidating the stereoselectivity of lipases in synthetic reactions of triacylglycerols has hitherto been carried out using traditional analytical techniques to determine the composition of the reaction products. These methods are laborious and are not always appropriate for analysis of certain triacylglycerol types. A direct method, utilizing a stereospecific deuterium‐labeled triacylglycerol substrate, has been developed where the stereoisomeric composition of the reaction product is determined by ultra‐high resolution 13C nuclear magnetic resonance (NMR) spectroscopy. Through lipase‐catalyzed transesterification of deuterium‐labeled trilauroylglycerol with oleic acid, chemical shifts were induced in the 13C NMR spectrum by the deuterium atom and olefinic double bonds, enabling unambiguous stereospecific assignment of triacylglycerol species. By this method of analysis, we found an effect of the degree of reaction conversion on the extent of stereoisomerism in the triacylglycerol product. Stereoselectivity was greatest (for sn‐1) with lipase from Rhizomucor miehei. Lipases from Rhizopus niveus, Candida rugosa, Carica papaya, and the cutinase from Fusarium sp. were also found to exhibit stereoselectivity, with preference for either sn‐1 or sn‐3 acyl exchange.

  DOI：

  10.1007/s11746-001-0370-4
• 作为产物：
  描述：

  在 水 、 氢气 作用下， 以0.6 g的产率得到sn-[3-2H1]-glycerol
  参考文献：
  名称：

  通过超高分辨率13C核磁共振测量脂肪酶催化酸解反应中的立体选择性

  摘要：

  AbstractElucidating the stereoselectivity of lipases in synthetic reactions of triacylglycerols has hitherto been carried out using traditional analytical techniques to determine the composition of the reaction products. These methods are laborious and are not always appropriate for analysis of certain triacylglycerol types. A direct method, utilizing a stereospecific deuterium‐labeled triacylglycerol substrate, has been developed where the stereoisomeric composition of the reaction product is determined by ultra‐high resolution 13C nuclear magnetic resonance (NMR) spectroscopy. Through lipase‐catalyzed transesterification of deuterium‐labeled trilauroylglycerol with oleic acid, chemical shifts were induced in the 13C NMR spectrum by the deuterium atom and olefinic double bonds, enabling unambiguous stereospecific assignment of triacylglycerol species. By this method of analysis, we found an effect of the degree of reaction conversion on the extent of stereoisomerism in the triacylglycerol product. Stereoselectivity was greatest (for sn‐1) with lipase from Rhizomucor miehei. Lipases from Rhizopus niveus, Candida rugosa, Carica papaya, and the cutinase from Fusarium sp. were also found to exhibit stereoselectivity, with preference for either sn‐1 or sn‐3 acyl exchange.

  DOI：

  10.1007/s11746-001-0370-4