1-palmitoyl-2-oleoyl-3-acetyl-sn-glycerol | 770728-82-0

• 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: 1-palmitoyl-2-oleoyl-3-acetyl-sn-glycerol
• 英文别名: [(2S)-1-acetyloxy-3-hexadecanoyloxypropan-2-yl] (Z)-octadec-9-enoate
• CAS: 770728-82-0
• 化学式: C₃₉H₇₂O₆
• 分子量: 636.997
• InChiKey: BFGDEKPANYJEBP-AMTAEZDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  45
• 可旋转键数：
  37
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  棕榈酸酐 、 1-O-tert-butyldimethylsilyl-2-oleoyl-3-acetyl-sn-glycerol 在 三甲基溴硅烷 、 四丁基溴化铵 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以93%的产率得到1-palmitoyl-2-oleoyl-3-acetyl-sn-glycerol
  参考文献：
  名称：

  O-甲硅烷基化的C3-卤代醇是一类新型的受保护的结构单元，可进行甘油脂骨架的完全，区域和立体控制合成†

  摘要：

  我们提出了O-甲硅烷基化的C3-卤代醇[1（3）-O-甲硅烷基-2- O-酰基-， 1,2（2,3）-O-双（甲硅烷基）-和1（3）-O-酰基-2- O-甲硅烷基-3（1）-卤代-sn-甘油酯]作为甘油脂质结构总合成中的新Chirons。这些可以通过打开环氧乙烷 相应的戒指 缩水甘油基 衍生物和许可（i）碘的必要置换 羧酸盐 在......的存在下 邻三异丙基甲硅烷基（O -TIPS），Ø -叔丁基二（O -TBDMS），和邻酰基取代基；（ii）在适当的范围内进行选择性酰化甲硅烷氧基系统[例如，Ò -TBDMS或邻三乙基甲硅烷基（O -TES）]的单酯化卤代甘油酯；（iii）将O-甲硅烷基保护基（例如，O- TBDMS或O- TIPS ）直接交换为三氯乙酰基；（iv）将终端TBDMS组转换为相应的三氟乙酸盐在不影响O -TIPS-的情况下，邻酰基-和碘功能。上述转换可确保向各种其他难以访问的密钥中间方提供灵活的路由[例如，1

  DOI：

  10.1039/b915533c

文献信息

• METHOD TO PRODUCE ACETYLDIACYLGLYCEROLS (AC-TAGS) BY EXPRESSION OF AN ACETYLTRANSFERASE GENE ISOLATED FROM EUONYMUS ALATUS (BURNING BUSH)
  申请人：Durrett Timothy

  公开号：US20130116462A1

  公开（公告）日：2013-05-09

  The present invention relates to novel diacylglycerol acyltransferase genes and proteins, and methods of their use. In particular, the invention describes genes encoding proteins having diacylglycerol acetyltransferase activity, specifically for transferring an acetyl group to a diacylglycerol substrate to form acetyl-Triacylglycerols (ac-TAGS), for example, a 3-acetyl-1,2-diacyl-sn-glycerol. The present invention encompasses both native and recombinant wild-type forms of the transferase, as well as mutants and variant forms. The present invention also relates to methods of using novel diacylglycerol acyltransferase genes and proteins, including their expression in transgenic organisms at commercially viable levels, for increasing production of 3-acetyl-1,2-diacyl-sn-glycerols in plant oils and altering the composition of oils produced by microorganisms, such as yeast, by increasing ac-TAG production. Additionally, oils produced by methods of the present inventions comprising genes and proteins are contemplated for use as biodiesel fuel, in polymer production and as naturally produced food oils with reduced calories.
• US9328335B2
  申请人：——

  公开号：US9328335B2

  公开（公告）日：2016-05-03
• [EN] A METHOD TO PRODUCE ACETYLDIACYLGLYCEROLS (AC-TAGS) BY EXPRESSION OFAN ACETYLTRANSFERASE GENE ISOLATED FROM EUONYMUS ALATUS (BURNING BUSH)<br/>[FR] PROCÉDÉ DE PRODUCTION D'ACÉTYLDIACYLGLYCÉROLS (AC-TAG) PAR EXPRESSION D'UN GÈNE D'ACÉTYLTRANSFÉRASE ISOLÉ À PARTIR D'EUONYMUS ALATUS (FUSAIN AILÉ)
  申请人：UNIV MICHIGAN STATE

  公开号：WO2011082253A2

  公开（公告）日：2011-07-07

  The present invention relates to novel diacylglycerol acyltransferase genes and proteins, and methods of their use. In particular, the invention describes genes encoding proteins having diacylglycerol acetyltransferase activity, specifically for transferring an acetyl group to a diacylglycerol substrate to form acetyl- Triacylglycerols (ac-TAGs), for example, a 3-acetyl-1,2-diacyl-sn-glycerol. The present invention encompasses both native and recombinant wild-type forms of the transferase, as well as mutants and variant forms. The present invention also relates to methods of using novel diacylglycerol acyltransferase genes and proteins, including their expression in transgenic organisms at commercially viable levels, for increasing production of 3 -acetyl- 1,2-diacyl-sn-glycerols in plant oils and altering the composition of oils produced by microorganisms, such as yeast, by increasing ac- TAG production. Additionally, oils produced by methods of the present inventions comprising genes and proteins are contemplated for use as biodiesel fuel, in polymer production and as naturally produced food oils with reduced calories.
• O-Silylated C3-halohydrins as a novel class of protected building blocks for total, regio- and stereocontrolled synthesis of glycerolipid frameworks
  作者：Stephan D. Stamatov、Jacek Stawinski

  DOI：10.1039/b915533c

  日期：——

  secure flexible routes to a variety of otherwise difficult-to-access key-intermediates [e.g., 1,2(2,3)-O-bis(acyl)-3(1)-trichloroacetyl-, 1,3-O-bis(acyl)-2-trichloroacetyl-, 1,2(2,3)-O-bis(acyl)-3(1)-O-TBDMS/TIPS-, 1,3-O-bis(acyl)-2-O-TIPS/TBDMS-, 1(3)-O-acyl-2-O-TIPS-, 1,2(2,3)-O-bis(acyl)-3(1)-iodo-sn-glycerols, etc.] and lend themselves to a powerful methodology for the preparation of di- and triacylglycerols

  我们提出了O-甲硅烷基化的C3-卤代醇[1（3）-O-甲硅烷基-2- O-酰基-， 1,2（2,3）-O-双（甲硅烷基）-和1（3）-O-酰基-2- O-甲硅烷基-3（1）-卤代-sn-甘油酯]作为甘油脂质结构总合成中的新Chirons。这些可以通过打开环氧乙烷 相应的戒指 缩水甘油基 衍生物和许可（i）碘的必要置换 羧酸盐 在......的存在下 邻三异丙基甲硅烷基（O -TIPS），Ø -叔丁基二（O -TBDMS），和邻酰基取代基；（ii）在适当的范围内进行选择性酰化甲硅烷氧基系统[例如，Ò -TBDMS或邻三乙基甲硅烷基（O -TES）]的单酯化卤代甘油酯；（iii）将O-甲硅烷基保护基（例如，O- TBDMS或O- TIPS ）直接交换为三氯乙酰基；（iv）将终端TBDMS组转换为相应的三氟乙酸盐在不影响O -TIPS-的情况下，邻酰基-和碘功能。上述转换可确保向各种其他难以访问的密钥中间方提供灵活的路由[例如，1