(2S)-1-O-β-D-galactopyranosyl-3-O-palmitoyl glyceride | 35949-84-9

• 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-β-D-galactopyranosyl-3-O-palmitoyl glyceride
• 英文别名: 1-Palmitoyl-galactosylglycerol；[(2S)-2-hydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] hexadecanoate
• CAS: 35949-84-9
• 化学式: C₂₅H₄₈O₉
• 分子量: 492.651
• InChiKey: DWKQIHQQZYILDB-DISYYVGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 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-β-D-galactopyranosyl-3-O-palmitoyl glyceride 在 Mucor javanics lipase 作用下， 以 二氯甲烷 为溶剂， 生成 Hexadecanoic acid (2R,3R,4S,5R,6R)-6-((S)-3-hexadecanoyloxy-2-hydroxy-propoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl 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：

  (9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid (S)-2-hexadecanoyloxy-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester 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 Hexadecanoic acid (R)-1-hydroxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester 、 (2S)-1-O-β-D-galactopyranosyl-3-O-palmitoyl glyceride
  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.
• 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。
• 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.