6'-O-lauroylmaltose

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 6'-O-lauroylmaltose
• 英文别名: lauroyl(-6)Glc(a1-4)Glc；[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl dodecanoate
• 化学式: C₂₄H₄₄O₁₂
• 分子量: 524.606
• InChiKey: RHKKOJKFAQAUGX-FFPITKCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  麦芽糖 、 月桂酸乙酯 在 3 A molecular sieve 、 lipase from Humicola lanuginosa immobilized on Celite 作用下， 以 2-甲基-2-丁醇 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成 6'-O-lauroylmaltose
  参考文献：
  名称：

  A Simple Procedure for the Regioselective Synthesis of Fatty Acid Esters of Maltose, Leucrose, Maltotriose and n-Dodecyl Maltosides

  摘要：

  The enzymatic acylation of several di- and trisaccharides with acyl donors ranging from 8 to 18 carbon atoms was carried out by transesterification with the corresponding vinyl esters. The reaction was performed in 2-methyl-2-butanol/dimethylsulfoxide mixtures using the lipase from Humicola lanuginosa (immobilized on Celite). Maltose, maltotriose and n-dodecyl maltosides were specifically acylated in the primary hydroxyl of the non-reducing-end glucose moiety; the acylation of leucrose occurred preferentially in the primary hydroxyl of the glucose ring. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00319-7

文献信息

• Effect of fatty acid chain length on initial reaction rates and regioselectivity of lipase-catalysed esterification of disaccharides
  作者：Ninfa R Pedersen、Reinhard Wimmer、Jeppe Emmersen、Peter Degn、Lars H Pedersen

  DOI：10.1016/s0008-6215(02)00112-x

  日期：2002.7

  t-BuOH and pyridine (v/v) the effect of fatty acid chain length (C-4-C-12) on C. antarctica lipase B (Novozym 435, EC 3.1.1.3) catalysed esterification was studied. alpha and beta maltose 6'-O-acyl esters in an anomeric molar ratio of 1.0:1.1 were synthesised independently of the chain length, but the initial specific reaction rate increased with decreasing chain length of the acyl donor. The product

  在9:11 t-BuOH和吡啶（v / v）的反应介质混合物中，脂肪酸链长（C-4-C-12）对南极洲C.脂肪酶B的影响（Novozym 435，EC 3.1.1.3）研究了催化酯化反应。异头摩尔比为1.0：1.1的α和β麦芽糖6'-O-酰基酯的合成与链长无关，但初始比反应速率随酰基供体链长的减小而增加。反应24小时后，产物产率遵循相同的趋势，月桂酸酯产率为1.1％（mol / mol），丁酯产率为27.6％（mol / mol）。以蔗糖为酰基受体时，链长为C-4和C-10的脂肪酸形成6'-O-酰基和6-O-酰基单酯，而6'，6-O-酰基二酯仅与丁酸（C-4：0）作为酰基供体。6' -O-酰基和6-O-酰基单酯和丁酸的6'，6-O-酰基二酯的摩尔比为1.0：0.5：0.2，癸酸（C-10：0）生成6 -O-酰基和6-O-酰基单酯以1.0∶0.3的比例形成。在酰基供体的链长度最短的情况下，可
• Chemical and biochemical studies on carbohydrate esters. IX. Antitumor effects of selectively fatty acylated products of maltose.
  作者：YOSHIHIRO NISHIKAWA、KIMIHIRO YOSHIMOTO、MUNEKAZU NISHIJIMA、FUMIKO FUKUOKA、TETSURO IKEKAWA

  DOI：10.1248/cpb.29.505

  日期：——

  Selective fatty acylation of maltose was carried out by heating an equimolar mixture of the disaccharide and an appropriate acid chloride in pyridine. The resulting crude product was chromatographed to furnish two preparations, termed maltose-[mono]- and-[high]-esters ; the former preparation was an isomeric mixture of monoesters among which the 1-, 6-, and 6'-isomers were presumably predominant, and the latter consisted of di-, tri-, and poly-esters, as indicated by gas-liquid and thin-layer chromatographies. The antitumor effects of the maltose-[mono]-esters of stearic, palmitic, myristic, lauric, and caprylic acids towards Ehrlich ascites carcinoma in mice were tested by the total packed cell volume method, by intraperitoneal injection. The stearic, palmitic, and myristic esters proved to be effective, while the lauric and caprylic esters exhibited a slight effect and no effect, respectively. The antitumor effect of the maltose-[mono]-stearate upon the same tumor was compared with that of the analogous derivative of sucrose by survival bioassay (intraperitoneal administration) at various doses. Both compounds showed similar antitumor results, giving especially marked effects at the dose of 50 mg/kg/day×5. These two compounds also exerted moderate growth-inhibitory effects against solid sarcoma 180 in mice when they were administered subcutaneously ; in the case of sucrose-[mono]-stearate, intramuscular injection was also effective. The maltose-[high]-esters of stearic, palmitic, and myristic acids failed to exert marked activity upon this solid tumor by either administration route.

  通过在吡啶中加热二糖和适当氯化酸的等摩尔混合物，对麦芽糖进行选择性脂肪酰化。前一种制剂是单酯的异构体混合物，其中 1-、6-和 6'-异构体可能占主导地位，而后一种制剂则由二酯、三酯和多酯组成，如气液相色谱法和薄层色谱法所示。硬脂酸、棕榈酸、肉豆蔻酸、月桂酸和辛酸的麦芽糖-[单]酯对小鼠艾氏腹水癌的抗肿瘤作用是通过腹腔注射总包装细胞体积法进行测试的。结果表明，硬脂酸、棕榈酸和肉豆蔻酸酯有效，而月桂酸和辛酸酯分别表现出轻微作用和无作用。通过不同剂量的存活生物测定（腹腔给药），比较了麦芽糖-[单]硬脂酸酯与蔗糖的类似衍生物对同一肿瘤的抗肿瘤作用。这两种化合物的抗肿瘤效果相似，在 50 毫克/千克/天×5 的剂量下效果尤为明显。这两种化合物皮下注射对小鼠实体肉瘤 180 也有中等程度的生长抑制作用；蔗糖-[单]硬脂酸酯肌肉注射也有效。硬脂酸、棕榈酸和肉豆蔻酸的麦芽糖-[高]酯无论通过哪种给药途径都无法对这种实体瘤产生明显的活性。