(2S)-3-O-(9Z,12Z-octadecadienoyl)glyceryl-β-D-galactopyranoside | 88110-55-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2S)-3-O-(9Z,12Z-octadecadienoyl)glyceryl-β-D-galactopyranoside
• 英文别名: (2S)-1-O-linoleoyl-3-O-β-D-galactopyranosyl-sn-glycerol；check stereo；[(2S)-2-hydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (9Z,12Z)-octadeca-9,12-dienoate
• CAS: 88110-55-8
• 化学式: C₂₇H₄₈O₉
• 分子量: 516.673
• InChiKey: LBHUIJRTHBBWHP-GRVKTFRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2 S)-1-O-β-D-galactopyranosyl-2-O-linoleoyl-3-O-linolenoyl glyceride 在 Rhizopus arrhizus lipase 、 boric acid-borax buffer 、 Triton X-100 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (9Z,12Z)-Octadeca-9,12-dienoic acid (R)-1-hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester 、 (2S)-3-O-(9Z,12Z-octadecadienoyl)glyceryl-β-D-galactopyranoside
  参考文献：
  名称：

  Enzymatic transformation of glyceroglycolipids into sn-1 and sn-2 lysoglyceroglycolipids by use of Rhizopus arrhizus lipase

  摘要：

  Lipase from Rhizopus arrhizus catalyzed deacylation of two classes of glyceroglycolipids, monogalactosyl diacylglycerol(MGDG), and digalactosyl diacylglycerol(DGDG), proceeded regiospecifically to furnish sn-1 lysoglyceroglycolipids quantitatively. The lipase also catalyzed complete acyl migration of sn-1 lysoglycerogalacto-lipids leading to sn-2 lysoglycerogalactolipids.

  DOI：

  10.1016/s0040-4020(01)85063-8

文献信息

• Enzymatic Regioselective Acylation of 3-O-.BETA.-D-Galactopyranosyl-sn-glycerol by Achromobacter sp. Lipase.
  作者：Takashi MORIMOTO、Nobutoshi MURAKAMI、Akito NAGATSU、Jinsaku SAKAKIBARA

  DOI：10.1248/cpb.42.751

  日期：——

  Achromobacter sp. lipase regioselectively acylated the hydroxyl group on sn-1 carbon among the two primary hydroxyl groups of 3-O-β-D-galactopyranosyl-sn-glycerol.

  Achromobacter sp. 脂肪酶选择性地对3-O-β-D-半乳糖吡喃糖基-sn-甘油的两个主要羟基中的sn-1碳上的羟基进行了酰化。
• Chemoenzymatic synthesis of 1-O-acyl-3-O-(6'-O-acyl-β-D-galactopyranosyl)-sn-glycerol
  作者：Takashi Morimoto、Akito Nagatsu、Nobutoshi Murakami、Jinsaku Sakakibara

  DOI：10.1016/0040-4020(95)00299-n

  日期：1995.6

  Convenient synthesis of 1-O-acyl-3-O-(6'-O-acyl-beta-D-galactopyranosyl)-sn-glycerol was studied. The lipase from Achromobacter sp, catalyzed acylation of 3-O-beta-D-galactopyranosyl-sn-glycerol, which contains two primary hydroxyl functions, proceeded regioselectively to furnish 1-O-acyl-3-O-beta-D-galactopyranosyl-sn-glycerol.
• Enzymatic transformation of glyceroglycolipids into sn-1 and sn-2 lysoglyceroglycolipids by use of Rhizopus arrhizus lipase
  作者：Nobutoshi Murakami、Takashi Morimoto、Hideaki Imamura、Akito Nagatsu、Jinsaku Sakakibara

  DOI：10.1016/s0040-4020(01)85063-8

  日期：1994.2

  Lipase from Rhizopus arrhizus catalyzed deacylation of two classes of glyceroglycolipids, monogalactosyl diacylglycerol(MGDG), and digalactosyl diacylglycerol(DGDG), proceeded regiospecifically to furnish sn-1 lysoglyceroglycolipids quantitatively. The lipase also catalyzed complete acyl migration of sn-1 lysoglycerogalacto-lipids leading to sn-2 lysoglycerogalactolipids.