2,3-二羟基丙基吡喃己糖苷 | 16232-91-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 2,3-二羟基丙基吡喃己糖苷
• 中文别名: (2R)-2,3-二羟基丙基-b-D-吡喃半乳糖苷；8-甲氧基羰基辛基2-脱氧-4,6-O-(4-甲氧基亚苄基)-2-邻苯二甲酰亚胺基-bD-吡喃葡萄糖苷
• 英文名称: (2R)-1-O-β-D-galactopyranosylglycerol
• 英文别名: 3-O-beta-D-galactosyl-sn-glycerol；Galactosylglycerol；(2R,3R,4S,5R,6R)-2-[(2R)-2,3-dihydroxypropoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 16232-91-0
• 化学式: C₉H₁₈O₈
• 分子量: 254.237
• InChiKey: NHJUPBDCSOGIKX-NTXXKDEISA-N

物化性质

• 熔点：
  140.5-141.5°C
• 溶解度：
  可溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3-二羟基丙基吡喃己糖苷 在 吡啶 、 Achromobacter sp. lipase 、 Mucor javanics lipase 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-Hexadec-9-enoic acid (2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((S)-2-hydroxy-3-tetradecanoyloxy-propoxy)-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：

  (2S)-1-O-linolenoyl-2-O-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol 在 甲醇 、 sodium methylate 作用下， 反应 15.0h， 生成 2,3-二羟基丙基吡喃己糖苷
  参考文献：
  名称：

  Glyceroglycolipids from Citrus hystrix, a Traditional Herb in Thailand, Potently Inhibit the Tumor-Promoting Activity of 12-O-Tetradecanoylphorbol 13-Acetate in Mouse Skin

  摘要：

  Two glyceroglycolipids were isolated from the leaves of Citrus hystrix (bitter orange), a traditional herb in Thailand. They were identified as 1,2-di-O-alpha-linolenoyl-3-O-beta-galactopyransyl-sn-glycerol (DLGG, I) and a mixture of two compounds, 1-O-alpha-linolenoyl-2-O-palmitoyl-3-O-beta-galactopyranosyl-sn-glycerol (2a) and its counterpart (2b) (LPGG, 2). Both lipids were potent inhibitors of tumor promoter-induced Epstein-Barr virus (EBV) activation. The IC50 values of 1 and 2 were strikingly lower than those of representative cancer preventive agents such as alpha-linolenic acid, beta-carotene, or (-)-epigallocatechin gallate. In a two-stage carcinogenesis experiment on ICR mouse skin with dimethylbenz[alpha]anthracene (DMBA) and 12-O-tetradecanoylphorbol 13-acetate (TPA), compound 1 exhibited anti-tumor-promoting activity even at a dose 10 times lower than that of alpha-linolenic acid. As some synthetic detergents or saponins were entirely inactive in the EBV activation inhibition test, detergency was suggested not to play a major role in the mode of inhibitory action in vivo. The inhibition of the arachidonic acid cascade may be involved in anti-tumor promotion since 1 inhibited TPA-induced edema formation in the anti-inflammation test using ICR mouse ears.

  DOI：

  10.1021/jf00058a043

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。
• Synthesis of α- and β-glycopyranosides via 1-0-alkylation
  作者：R.R. Schmidt、U. Moering、M. Reichrath

  DOI：10.1016/0040-4039(80)80236-x

  日期：1980.1

  1-0-Alkylation of partly protected glucopyranose 1 and galactopyranose 13 led to a convenient, short term synthesis of β-glycosides and β-disaccharides 4a–d and 14. Glucopyranose 2 with a bulky protective group at 0–6 yielded exclusively the α-anomer (isomaltoside derivative) 5.

  部分保护的吡喃葡萄糖1和半乳糖吡喃糖13的1-0烷基化导致β-糖苷和β-二糖4a-d和14的便捷，短期合成。在0-6带有较大保护基的葡糖醛糖2仅产生α。 -异头物（异麦芽糖苷衍生物）5。
• Exploring the Binding Proteins of Glycolipids with Bifunctional Chemical Probes
  作者：Xiaohui Liu、Ting Dong、Yu Zhou、Niu Huang、Xiaoguang Lei

  DOI：10.1002/anie.201608827

  日期：2016.11.7

  Glycolipids are important structural components of biological membranes and perform crucial functions in living systems, including signaling transduction and interaction with extracellular environment. However, the mechanistic exploration of glycolipids in vivo is challenging because they are not genetically encoded. Herein, we designed and synthesized a series of bifunctional monogalactosyldiacylglycerol

  糖脂是生物膜的重要结构成分，在生命系统中起着至关重要的作用，包括信号转导和与细胞外环境的相互作用。然而，体内糖脂的机械探索是具有挑战性的，因为它们不是遗传编码的。在本文中，我们通过在脂肪族链上引入重氮基和末端炔基部分，设计并合成了一系列双功能单半乳糖基二酰基甘油（MGDG）探针作为模型。结合蛋白质组分析和分子建模，我们已证明MGDG通过拮抗TLR4减轻炎症。
• Studies on Glycolipids. III. Glyceroglycolipids from an Axenically Cultured Cyanobacterium, Phormidium tenue.
  作者：Nobutoshi MURAKAMI、Takashi MORIMOTO、Hideaki IMAMURA、Taisei UEDA、Shin-ichi NAGAI、Jinsaku SAKAKIBARA、Naoki YAMADA

  DOI：10.1248/cpb.39.2277

  日期：——

  Seven new monogalactosyl diacylglycerols (1-7) and six new digalactosyl diacylglycerols (11-16) were isolated from an axenically cultured cyanobacterium, P. tenue. Their structures were elucidated on the basis of physicochemical evidence and the results of enzymatic hydrolysis using a lipase (from Rhizopus arrhizus). Comparison of antialgal activity for P. tenue between monogalactosyl diacylglycerols (1-8)

  从树胶培养的蓝细菌P. tenue中分离出七种新的单半乳糖基二酰基甘油（1-7）和六种新的二半乳糖基二酰基甘油（11-16）。根据理化证据和使用脂肪酶（来自阿魏根霉）的酶促水解结果，阐明了它们的结构。单半乳糖基二酰基甘油（1-8）和二半乳糖基二酰基甘油（11-19）之间对P. tenue的抗藻活性比较表明，前者的活性比后者强。
• Cerebrosides and a Monoacylmonogalactosylglycerol from Clinacanthus nutans
  作者：Pittaya Tuntiwachwuttikul、Yupa Pootaeng-on、Photchana Phansa、Walter Charles Taylor

  DOI：10.1248/cpb.52.27

  日期：——

  A mixture of nine cerebrosides and a monoacylmonogalactosylglycerol were seperated from the leaves of Clinacanthus nutans. The structures of the cerebrosides were characterized as 1-O-β-D-glucosides of phytosphingosines, which comprised a common long-chain base, (2S,3S,4R,8Z)-2-amino-8(Z)-octadecene-1,3,4-triol with nine 2-hydroxy fatty acids of varying chain lengths (C16, C18, C20—26) linked to the amino group. The glycosylglyceride was characterized as (2S)-1-O-linolenoyl-3-O-β-D-galactopyranosylglycerol. The structures were established on the basis of the spectroscopic data and chemical reactions.

  从坚果蕨（Clinacanthus nutans）叶片中分离出了由九种脑苷脂和一种单酰基半乳糖甘油组成的混合物。这些脑苷脂的结构被表征为植物鞘氨醇的 1-O-β-<小>D-葡萄糖苷，由一个共同的长链基团 (2S,3S,4R,8Z)-2-氨基-8(Z)-十八烯-1,3,4-三醇和九个不同链长（C16、C18、C20-26）的 2-羟基脂肪酸组成，与氨基相连。这种糖基甘油的特征是(2S)-1-O-亚麻酰基-3-O-β-<小>D-吡喃半乳糖基甘油。这些结构是根据光谱数据和化学反应确定的。