methyl O-β-D-galactopyranosyl-(1<*>4)-O-β-D-glucopyranosyl-(1<*>4)-β-D-glucopyranoside

• 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-galactopyranosyl-(1<*>4)-O-β-D-glucopyranosyl-(1<*>4)-β-D-glucopyranoside
• 英文别名: Gal(b1-4)Glc(b1-4)b-Glc1Me；(2S,3R,4S,5R,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
• 化学式: C₁₉H₃₄O₁₆
• 分子量: 518.469
• InChiKey: YHLYETOEEVCCRS-BMVBQHAQSA-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：

  乙酸酐 、 methyl O-β-D-galactopyranosyl-(1<*>4)-O-β-D-glucopyranosyl-(1<*>4)-β-D-glucopyranoside 以 吡啶 为溶剂， 以105 mg的产率得到methyl 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-β-D-glucopyranoside
  参考文献：
  名称：

  Transglycosylation reactions with a crude culture filtrate from Thermoascusaurantiacus

  摘要：

  Some characteristics of regioselectivity and acceptor tolerance in transglycosylation reactions, catalysed by a crude culture filtrate from Thermoascus aurantiacus, were examined by employing methanol and monosaccharides as accepters. When beta-D-mannopyranosyl fluoride was employed as the donor, the anomeric configuration of the newly formed bond was found to depend on the structure of the acceptor used. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00061-6
• 作为产物：
  描述：

  β-lactosyl fluoride 、 甲基 Β-D-吡喃葡萄糖苷 在 acetate buffer 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以51%的产率得到methyl O-β-D-galactopyranosyl-(1<*>4)-O-β-D-glucopyranosyl-(1<*>4)-β-D-glucopyranoside
  参考文献：
  名称：

  Cellulase-catalysed, stereoselective synthesis of oligosaccharides

  摘要：

  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。

  DOI：

  10.1039/c39930001402

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。
• A facile enzymatic synthesis of cellooligosaccharide derivatives using β-lactosyl fluoride
  作者：Shin-ichiro Shoda、Tatsuya Kawasaki、Kei Obata、Shiro Kobayashi

  DOI：10.1016/0008-6215(93)84066-f

  日期：1993.10

  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.
• 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：——
• Transglycosylation reactions with a crude culture filtrate from Thermoascusaurantiacus
  作者：Jörg Ortner、Martin Albert、Katherine Terler、Walter Steiner、Karl Dax

  DOI：10.1016/s0008-6215(00)00061-6

  日期：2000.8

  Some characteristics of regioselectivity and acceptor tolerance in transglycosylation reactions, catalysed by a crude culture filtrate from Thermoascus aurantiacus, were examined by employing methanol and monosaccharides as accepters. When beta-D-mannopyranosyl fluoride was employed as the donor, the anomeric configuration of the newly formed bond was found to depend on the structure of the acceptor used. (C) 2000 Elsevier Science Ltd. All rights reserved.