methyl O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside | 78853-87-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: methyl β-D-glucopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside；methyl β-D-cellotriose；methyl β-cellotrioside；Glc(b1-4)Glc(b1-4)b-Glc1Me；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 78853-87-9
• 化学式: C₁₉H₃₄O₁₆
• 分子量: 518.469
• InChiKey: YHLYETOEEVCCRS-ZBQKSBIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  258
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside 在 盐酸 、 bicarbonate buffer 、 Cel₇B E₁₉₇A 、 碳酸根离子 作用下， 反应 15.08h， 生成 methyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Stepwise synthesis of cellodextrins assisted by a mutant cellulase

  摘要：

  摘要 4Ⅱ保护的α-纤维二糖酰氟是一种高效的供体，可通过酶促作用逐步缩合到甲基ß-D-糖苷受体上。在 Humicola insolens 的 Cel7B E197A 糖合成酶的催化下，这些反应可以高产率地得到聚合度为 3 到 6 的纤维糊精。

  DOI：

  10.1560/5ncy-l9k2-jnd4-mb6q
• 作为产物：
  描述：

  甲基 4-O-beta-D-吡喃葡萄糖基-beta-D-吡喃葡萄糖苷 以 甲醇 为溶剂， 反应 6.5h， 生成 methyl O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  A facile enzymatic synthesis of cellooligosaccharide derivatives using β-lactosyl fluoride

  摘要：

  A convenient method for the preparation of cellooligosaccharide derivatives has been developed that uses beta-lactosyl fluoride as the glycosyl donor, The reaction consists of the following enzymatic processes; (1) a cellulase-catalyzed regio- and stereo-selective lactosylation of a beta-cellobioside as the glycosyl acceptor, utilizing the transglycosylating ability of an enzyme-substrate complex formed from beta-lactosyl fluoride and cellulase; (2) beta-D-galactosidase-catalyzed regioselective cleavage of the terminal D-galactose unit from the lactosylated product, giving rise to a beta-cellotrioside derivative. A cellotetraoside derivative has successfully been prepared in a stereo- and regio-selective manner by repeating these enzymatic reactions and using the resulting beta-cellotrioside as starting material.

  DOI：

  10.1016/0008-6215(93)84066-f

文献信息

• Cellulase-catalysed, stereoselective synthesis of oligosaccharides
  作者：Shin-Ichiro Shoda、Kei Obata、Olaf Karthaus、Shiro Kobayashi

  DOI：10.1039/c39930001402

  日期：——

  Oligosaccharides are synthesised enzymatically using β-lactosyl fluoride as glycosyl donor and a variety of mono-, di-and tri-saccharides as acceptors; the nature of the active site of the catalyst cellulase is discussed on the basis of these reactions.

  低聚糖通过酶法合成，以β-乳糖基氟化物为糖基供体，多种单糖、二糖和三糖作为受体；根据这些反应，探讨了催化剂纤维素酶活性中心的性质。
• Synthesis of cellobiose, cellotriose, cellotetraose, and lactose
  作者：Ken'ichi Takeo、Kazuo Okushio、Katsumi Fukuyama、Takashi Kuge

  DOI：10.1016/0008-6215(83)84014-2

  日期：1983.9

  presence of mercuric cyanide gave, in 86% yield after O -deacetylation followed by column chromatography, benzyl 2,3,6-tri- O -benzyl-β-cellobioside, which was catalytically hydrogenolyzed to afford cellobiose. In a similar way, methyl α-cellobioside, cellotriose, methyl α- and β-cellotriosides, cellotetraose, lactose, and methyl α-lactoside were synthesized with high stereospecificity and in good yield

  摘要1,3,4,6-四-O-乙酰基-α-d-吡喃葡萄糖基溴化物（1）与1,2,3,6-三-O-苄基-β-d-吡喃葡萄糖苷（6）的缩合反应在氰化汞存在下，用1：1的苯-硝基甲烷进行O-脱乙酰化，然后进行柱色谱纯化，产率为86％，将苄基2,3,6-三-O-苄基-β-纤维二糖苷催化水解生成纤维二糖。以类似的方式，使用甲基2,3,6，通过偶联反应以高立体特异性和高收率合成了甲基α-纤维二糖苷，纤维三糖，甲基α-和β-纤维糖苷，纤维四糖，乳糖和甲基α-乳糖苷。 -三-O-苄基-α-和-β-d-吡喃葡萄糖苷6和苄基2,3,6,2'，3'，6'-六-O-苄基-β-纤维二糖苷作为糖基受体，和1,2,3,4,6-四-O-乙酰基-α-d-吡喃半乳糖基溴化物，
• Phosphorolytic synthesis of cellodextrins
  作者：Eric Samain、Christine Lancelon-Pin、Frédéric Férigo、Vincent Moreau、Henri Chanzy、Alain Heyraud、Hugues Driguez

  DOI：10.1016/0008-6215(95)00022-l

  日期：1995.7

  Transglucosylation reactions catalyzed by cellodextrin phosphorylase from Clostridium thermocellum were reinvestigated by using a series of cellobiosyl residues as glycosyl acceptors and α- d -glucopyranosyl phosphate (Glc-1-P) as glycosyl donor. When cellobiose was used as an acceptor, various unsubstituted cellodextrins, ranging from water-soluble products to crystalline precipitates were obtained

  摘要以一系列纤维二糖基残基为糖基受体，以α-d-葡萄糖基吡喃糖基磷酸酯（Glc-1-P）为糖基供体，对热纤梭菌纤维糊精磷酸化酶催化的葡萄糖基转移反应进行了研究。当纤维二糖用作受体时，取决于受体中的浓度，获得了从水溶性产物到结晶沉淀物的各种未取代的纤维糊精。4-硫代纤维二糖，甲基β-纤维二糖苷和甲基4-硫代-α-纤维二糖苷也可以以与纤维二糖相同的效率用作受体。当使用带有强疏水性糖苷配基的β-纤维二糖苷时，该酶表现出更高的活性。使用1：1实际制备了甲基β-纤维虫苷，纤维四糖苷和cellopentaoside。
• Isolation, Modification, and NMR Assignments of a Series of Cellulose Oligomers
  作者：Lisa A. Flugge、Jarred T. Blank、Peter A. Petillo

  DOI：10.1021/ja990561u

  日期：1999.8.1

  A homologous series of cellulose oligomers from two to eight repeating subunits have been isolated and size-fractionated from the hydrolysis products of microcrystalline cellulose. Chemical modification of cellotriose (1), cellotetraose (2), cellopentaose (3), and cellohexaose (4) to the corresponding β-methyl glycosides 13−16 proceeded in three steps in overall yields of 16−46%. Peracetylation produced

  已经从微晶纤维素的水解产物中分离并按尺寸分级了一系列同源系列的纤维素低聚物，它们由 2 到 8 个重复亚基组成。将纤维三糖 (1)、纤维四糖 (2)、纤维五糖 (3) 和纤维六糖 (4) 化学修饰成相应的 β-甲基糖苷 13-16 分三步进行，总产率为 16-46%。全乙酰化以 70-75% 的产率产生低聚物 5-8，随后形成的 β-甲基糖苷以 42-89% 的产率产生 9-12。使用胍去除乙酸盐保护基团提供了 13-16，产率为 73-79%。这种修改消除了异头平衡，并允许对这些低聚物进行详细的 NMR 溶液研究。通过 DQF-COSY、HMQC、HMBC 和 HMQC-TOCSY 实验的组合，获得了每个全乙酰化和脱保护低聚物的完整 1H 和 13C 化学位移分配。甲基纤维三糖 (13) 和甲基纤维四糖 (14) 中的所有共振都很容易区分...
• Karthaus, Olaf; Shoda, Shin-ichiro; Takano, Hiroshi, Journal of the Chemical Society. Perkin transactions I, 1994, # 13, p. 1851 - 1858
  作者：Karthaus, Olaf、Shoda, Shin-ichiro、Takano, Hiroshi、Obata, Kei、Kobayashi, Shiro

  DOI：——

  日期：——