Palmitoleyl oleate

• 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: Palmitoleyl oleate
• 英文别名: [(Z)-hexadec-9-enyl] (Z)-octadec-9-enoate
• 化学式: C₃₄H₆₄O₂
• 分子量: 504.9
• InChiKey: XGLAPGGDOHJURU-KXYOHKLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  36
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (9Z)-9-十六碳烯-1-醇 、 oleoyl-CoA(4-) 生成 Palmitoleyl oleate 、 coenzyme A
  参考文献：
  名称：

  Identification of Two Novel Human Acyl-CoA Wax Alcohol Acyltransferases

  摘要：

  The esterification of alcohols such as sterols, diacylglycerols, and monoacylglycerols with fatty acids represents the formation of both storage and cytoprotective molecules. Conversely, the overproduction of these molecules is associated with several disease pathologies, including atherosclerosis and obesity. The human acyl-CoA:diacylglycerol acyltransferase (DGAT) 2 gene superfamily comprises seven members, four of which have been previously implicated in the synthesis of di- or triacylglycerol. The remaining 3 members comprise an X-linked locus and have not been characterized. We describe here the expression of DGAT2 and the three X-linked genes in Saccharomyces cerevisiae strains virtually devoid of neutral lipids. All four gene products mediate the synthesis of triacylglycerol; however, two of the X-linked genes act as acyl-CoA wax alcohol acyltransferases (AWAT 1 and 2) that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. AWAT1 and AWAT2 have very distinct substrate preferences in terms of alcohol chain length and fatty acyl saturation. The enzymes are expressed in many human tissues but predominate in skin. In situ hybridizations demonstrate a differentiation-specific expression pattern within the human sebaceous gland for the two AWAT genes, consistent with a significant role in the composition of sebum.

  DOI：

  10.1074/jbc.m500025200

文献信息

• Identification of Two Novel Human Acyl-CoA Wax Alcohol Acyltransferases
  作者：Aaron R. Turkish、Annette L. Henneberry、Debra Cromley、Mahajabeen Padamsee、Peter Oelkers、Hisham Bazzi、Angela M. Christiano、Jeffrey T. Billheimer、Stephen L. Sturley

  DOI：10.1074/jbc.m500025200

  日期：2005.4

  The esterification of alcohols such as sterols, diacylglycerols, and monoacylglycerols with fatty acids represents the formation of both storage and cytoprotective molecules. Conversely, the overproduction of these molecules is associated with several disease pathologies, including atherosclerosis and obesity. The human acyl-CoA:diacylglycerol acyltransferase (DGAT) 2 gene superfamily comprises seven members, four of which have been previously implicated in the synthesis of di- or triacylglycerol. The remaining 3 members comprise an X-linked locus and have not been characterized. We describe here the expression of DGAT2 and the three X-linked genes in Saccharomyces cerevisiae strains virtually devoid of neutral lipids. All four gene products mediate the synthesis of triacylglycerol; however, two of the X-linked genes act as acyl-CoA wax alcohol acyltransferases (AWAT 1 and 2) that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. AWAT1 and AWAT2 have very distinct substrate preferences in terms of alcohol chain length and fatty acyl saturation. The enzymes are expressed in many human tissues but predominate in skin. In situ hybridizations demonstrate a differentiation-specific expression pattern within the human sebaceous gland for the two AWAT genes, consistent with a significant role in the composition of sebum.