(2S)-1-O-palmitoleyl-3-O-β-D-galactopyranosylglycerol | 157807-76-6

• 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-palmitoleyl-3-O-β-D-galactopyranosylglycerol
• 英文别名: 1-O-palmitoleoyl-3-O-β-D-galactopyranosyl-sn-glycerol；[(2S)-2-hydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (Z)-hexadec-9-enoate
• CAS: 157807-76-6
• 化学式: C₂₅H₄₆O₉
• 分子量: 490.635
• InChiKey: MEIYDPOVJHMEJK-SYPLSTJXSA-N

物化性质

• 沸点：
  670.2±55.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  十六酸乙烯酯 、 (2S)-1-O-palmitoleyl-3-O-β-D-galactopyranosylglycerol 在 Mucor javanics lipase 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-Hexadec-9-enoic acid (S)-3-((2R,3R,4S,5R,6R)-6-hexadecanoyloxymethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-2-hydroxy-propyl ester
  参考文献：
  名称：

  Antitumor-Promoting Activities of Various Synthetic 1-O-Acyl-3-O-(6'-O- Acyl-.BETA.-D-Galactopyranosyl)-sn-Glycerols Related to Natural Product from Freshwater Cyanobacterium Anabaena flos-aquae f.flos-aquae.

  摘要：

  利用脂肪酶催化酰化作用合成了 1-O-酰基-3-O-(6'-O-酰基-β-D-吡喃半乳糖基-sn-甘油，它是从固氮淡水蓝藻 Anabaena flos-aquae f. flos-aquae 中分离出来的。利用 12-O-十四碳酰基-抗坏血酸 13-乙酸酯（TPA）诱导的 Raji 细胞 Epstein-Barr 病毒活化体外短期试验，对这些半乳糖脂的抗肿瘤促进活性进行了评估。在该试验中，1-O 位具有棕榈油酰残基的甘油三酯比其他甘油三酯具有更强的活性。

  DOI：

  10.1248/cpb.44.1404
• 作为产物：
  描述：

  vinyl palmitoleate 、 2,3-二羟基丙基吡喃己糖苷 以 吡啶 为溶剂， 反应 72.0h， 生成 3-O-(6'-O-palmitoleoyl-β-D-galactopyranosyl)-sn-glycerol 、 (2S)-1-O-palmitoleyl-3-O-β-D-galactopyranosylglycerol
  参考文献：
  名称：

  Enzymatic Regioselective Acylation of 3-O-.BETA.-D-Galactopyranosyl-sn-glycerol by Achromobacter sp. Lipase.

  摘要：

  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。

  DOI：

  10.1248/cpb.42.751

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.
• Antitumor-Promoting Activities of Various Synthetic 1-O-Acyl-3-O-(6'-O- Acyl-.BETA.-D-Galactopyranosyl)-sn-Glycerols Related to Natural Product from Freshwater Cyanobacterium Anabaena flos-aquae f.flos-aquae.
  作者：Hideaki SHIRAHASHI、Takashi MORIMOTO、Akito NAGATSU、Nobutoshi MURAKAMI、Kazuhiro TATTA、Jinsaku SAKAKIBARA、Harukuni TOKUDA、Hoyoku NISHINO

  DOI：10.1248/cpb.44.1404

  日期：——

  1-O-Acyl-3-O-(6'-O-acyl-β-D-galactopyranosyl-sn-glycerol, which was isolated from a nitrogen-fixing freshwater cyanobacterium, Anabaena flos-aquae f. flos-aquae, was synthesized by utilizing lipase-catalyzed acylation.The antitumor-promoting activities of these galactolipids were evaluated using a short-term in vitro assay of Epstein-Barr virus activation in Raji cells induced by 12-O-tetradecanoyl-phorbol 13-acetate (TPA). The glyceroglycolipids which have a palmitoleoyl residue at the 1-O-position exhibited more potent activities than the others in this assay.

  利用脂肪酶催化酰化作用合成了 1-O-酰基-3-O-(6'-O-酰基-β-D-吡喃半乳糖基-sn-甘油，它是从固氮淡水蓝藻 Anabaena flos-aquae f. flos-aquae 中分离出来的。利用 12-O-十四碳酰基-抗坏血酸 13-乙酸酯（TPA）诱导的 Raji 细胞 Epstein-Barr 病毒活化体外短期试验，对这些半乳糖脂的抗肿瘤促进活性进行了评估。在该试验中，1-O 位具有棕榈油酰残基的甘油三酯比其他甘油三酯具有更强的活性。