(2S)-1-O-(9Z,12Z,15Z)-octadecatrienoyl-2-O-tetradecenoyl-3-O-<α-D-galactopyranosyl(1-6)-β-D-galactopyranosyl>-sn-glycerol | 134276-77-0

• 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)-1-O-(9Z,12Z,15Z)-octadecatrienoyl-2-O-tetradecenoyl-3-O-<α-D-galactopyranosyl(1-6)-β-D-galactopyranosyl>-sn-glycerol
• 英文别名: Ccris 8000；[(2S)-2-tetradecanoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• CAS: 134276-77-0
• 化学式: C₄₇H₈₂O₁₅
• 分子量: 887.159
• InChiKey: BFANANPGNZIJMK-YQZUWNISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  62
• 可旋转键数：
  37
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  231
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (2S)-1-O-(9Z,12Z,15Z)-octadecatrienoyl-2-O-tetradecenoyl-3-O-<α-D-galactopyranosyl(1-6)-β-D-galactopyranosyl>-sn-glycerol 在 boric acid-borax buffer 、 Triton X-100 作用下， 反应 1.0h， 生成 Tetradecanoic acid (R)-1-hydroxymethyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-ethyl ester
  参考文献：
  名称：

  Selective preparation of sn-1 and sn-2 lysogalactolipids by enzymatic hydrolysis using lipase (from Rhizopus arrhizus)

  摘要：

  Selective and quantitative transformations of galactolipids into sn-1 and sn-2 lysogalactolipids by the use of lipase (from Rhizopus arrhizus) were developed.

  DOI：

  10.1016/s0040-4039(00)79660-2
• 作为产物：
  描述：

  在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.75h， 生成 (2S)-1-O-(9Z,12Z,15Z)-octadecatrienoyl-2-O-tetradecenoyl-3-O-<α-D-galactopyranosyl(1-6)-β-D-galactopyranosyl>-sn-glycerol
  参考文献：
  名称：

  Synthesis of digalactosyl diacylglycerols and their structure–inhibitory activity on human lanosterol synthase

  摘要：

  Digalactosyl and monogalactocyl diacylglycerols (DGDG and MGDG), which were identified as anti-hyperlipemia active components in Colocasia esculenta (Taro), were synthesized. The inhibitory activity of DGDG, MGDG and related compounds on human lanosterol synthase was evaluated as anti-hyperlipemic activity. DGDG with two myristoyl groups at both sn-1 and sn-2 positions and with an oleoyl group at the sn-1 position showed the most potent activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.013

文献信息

• Selective preparation of sn-1 and sn-2 lysogalactolipids by enzymatic hydrolysis using lipase (from Rhizopus arrhizus)
  作者：Nobutoshi Murakami、Hideaki Imamura、Takashi Morimoto、Taisei Ueda、Shin-ichi Nagai、Jinsaku Sakakibara、Naoki Yamada

  DOI：10.1016/s0040-4039(00)79660-2

  日期：1991.3

  Selective and quantitative transformations of galactolipids into sn-1 and sn-2 lysogalactolipids by the use of lipase (from Rhizopus arrhizus) were developed.
• Synthesis of digalactosyl diacylglycerols and their structure–inhibitory activity on human lanosterol synthase
  作者：Rie Tanaka、Yuichi Sakano、Akito Nagatsu、Masaaki Shibuya、Yutaka Ebizuka、Yukihiro Goda

  DOI：10.1016/j.bmcl.2004.10.013

  日期：2005.1

  Digalactosyl and monogalactocyl diacylglycerols (DGDG and MGDG), which were identified as anti-hyperlipemia active components in Colocasia esculenta (Taro), were synthesized. The inhibitory activity of DGDG, MGDG and related compounds on human lanosterol synthase was evaluated as anti-hyperlipemic activity. DGDG with two myristoyl groups at both sn-1 and sn-2 positions and with an oleoyl group at the sn-1 position showed the most potent activity. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.