α-maltosyl α-glucoside | 103093-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-maltosyl α-glucoside
• 英文别名: O-α-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl-α-D-glucopyranoside；Bemisiose；(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 103093-92-1
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: CAKGLMPBYAPFCR-UWBMNBDUSA-N

物化性质

• 沸点：
  871.3±65.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  O-(2",3",4",6"-tetra-O-benzyl-α-D-glucopyranosyl)-(1"-> 4')-(2',3',6'-tri-O-benzyl-α-D-glucopyranosyl) 2,3-di-O-benzyl-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 生成 α-maltosyl α-glucoside
  参考文献：
  名称：

  具有（1 4）-键的α-D-糖基取代的α，α-D-海藻糖的合成和NMR研究

  摘要：

  两个对称的海藻糖的糖基“受体” 4和6中制备和三个非对称型的，8，10，和11。对称的“受体” 4的糖基化比保护ve-基团操纵（即通过选择性脱苄基2 9或单乙酰化2 5）获得的三糖收率更高（44％），中等收率（33-34％）。海藻糖“受体” 10与四-O-苄基-β-D-吡喃葡萄糖基氟13的顺式-葡萄糖基化反应中催化剂的比较异三氟甲磺酸酐（（Tf）2 O）作为新的反应性启动子，产生92％的三糖14，解封得到目标糖α-D-吡喃葡萄糖基-（1 4）-α，α-D-海藻糖。对大多数化合物的1 H-NMR光谱进行了广泛的分析。提倡使用ID TOCSY技术的时间效率，如果需要的话还可以通过ROESY实验进行补充。

  DOI：

  10.1002/hlca.19910740403

文献信息

• Formation of Trehalose from Maltooligosaccharides by a Novel Enzymatic System
  作者：Kazuhiko Maruta、Tetsuya Nakada、Michio Kubota、Hiroto Chaen、Toshiyuki Sugimoto、Masashi Kurimoto、Yoshio Tsujisaka

  DOI：10.1271/bbb.59.1829

  日期：1995.1

  A trehalose-producing bacterium, Arthrobacter sp. strain Q36, was isolated from soil. From a supernatant of the culture broth, two novel enzymes related to trehalose synthesis were partially purified by Sepabeads FP-DA column chromatography. One enzyme catalyzed the conversion of maltopentaose into maltotriosyl trehalose by intramolecular transglycosylation, showing it to be maltooligosyl trehalose synthase. The other hydrolyzed the product transferred by the former into maltotriose and trehalose specifically, showing it to be maltooligosyl trehalose trehalohydrolase. In addition to the bacterial strain isolated, several bacteria kept in our laboratory were found to produce these enzymes. The enzymatic system was proposed to be a novel biosynthesis of trehalose in bacteria involving the following reactions: maltodextrin→maltooligosyl trehalose, maltooligosyl trehalose→maltodextrin + trehalose. When these enzymes acted on amylose simultaneously, the trehalose in the reaction mixture reached more than 80% in content.

  从土壤中分离出了一种产生曲哈糖的细菌--节杆菌 Q36 菌株。通过 Sepabeads FP-DA 柱色谱法，从培养液的上清液中部分纯化出两种与三卤糖合成有关的新型酶。一种酶通过分子内转糖基化催化麦芽酮戊糖转化为麦芽三糖，表明它是麦芽寡糖三糖合成酶。另一种则将前者转移的产物特异性地水解为麦芽三糖和曲哈糖，表明它是麦芽寡糖基曲哈糖曲哈水解酶。除了分离出的细菌菌株外，我们还发现实验室中的几种细菌也能产生这些酶。该酶系统被认为是细菌中一种新型的三卤糖生物合成方法，涉及以下反应：麦芽糊精→麦芽寡糖基三卤糖，麦芽寡糖基三卤糖→麦芽糊精+三卤糖。当这些酶同时作用于直链淀粉时，反应混合物中的三卤糖含量达到 80% 以上。
• Synthesis of Glycosyl-trehaloses by Cyclomaltodextrin Glucanotransferase through the Transglycosylation Reaction
  作者：Masashi Kurimoto、Akihiko Tabuchi、Takahiko Mandai、Takashi Shibuya、Hiroto Chaen、Shigeharu Fukuda、Toshiyuki Sugimoto、Yoshio Tsujisaka

  DOI：10.1271/bbb.61.1146

  日期：1997.1

  Cyclomaltodextrin glucanotransferase from Bacillus stearothermophilus produced a series of glycosyl-trehaloses through the transglycosylation reaction with cyclomaltohexaose as the glycosyl donor and trehalose as its acceptor. After β-amylase treatment, five species of glycosyl-trehaloses were isolated by column chromatography. After chemical and enzymatic analyses, it was concluded that these oligosaccharides were α-maltosyl α-d-glucopyranoside, α-maltotriosyl α-d-glucopyranoside, α-maltosyl α-maltoside, α-maltotriosyl α-maltoside, and α-maltotriosyl α-maltotrioside. These were not hydrolyzed by salivary amylase, artificial gastric juice, or pancreatic amylase, however they were hydrolyzed by enzymes of the small intestine.

  嗜热脂肪芽孢杆菌的环麦芽糊精葡聚糖转移酶以环己糖为糖基供体，以曲哈糖为受体，通过转糖基化反应产生了一系列糖基曲哈糖。经过β-淀粉酶处理后，通过柱层析分离出了五种糖基-曲哈糖。经过化学和酶学分析，这些低聚糖分别是 α-麦芽糖基 α-d-吡喃葡萄糖苷、α-麦芽三糖基 α-d-吡喃葡萄糖苷、α-麦芽糖基 α-麦芽糖苷、α-麦芽三糖基 α-麦芽糖苷和 α-麦芽三糖基 α-麦芽三糖苷。这些物质不会被唾液淀粉酶、人工胃液或胰淀粉酶水解，但会被小肠酶水解。
• Regioselective syntheses of trehalose-containing trisaccharides using various glycohydrolases
  作者：Katsumi Ajisaka、Hiroshi Fujimoto

  DOI：10.1016/0008-6215(90)84264-u

  日期：1990.6

  Two methods were investigated for the enzymic preparation of trehalose-containing trisaccharides. In the first, a solution of saccharides is circulated through an immobilized-glycosidase column and an activated-carbon column connected in series. In the second, two enzymes having different substrate specificities are sequentially used for condensation and subsequent specific hydrolysis. Thus, 3-O-beta-D-, 4-O-beta-D-, and 6-O-beta-D-galactopyranosyl-alpha,alpha-trehalose; 4-O-alpha-D- and 6-O-alpha-D-glucopyranosyl-alpha,alpha-trehalose; and 4-O-beta-D- and 6-O-beta-D-glucopyranosyl-alpha,alpha-trehalose were synthesized stereo- and regio-selectively.
• ?-D-Glycosyl-Substituted ?,?-D-Trehaloses with (1 ? 4)-Linkage: Syntheses and NMR Investigations
  作者：Hans Peter Wessel、Gerhard Englert、Peter Stangier

  DOI：10.1002/hlca.19910740403

  日期：1991.6.19

  Two symmetrical trehalose glycosyl ‘acceptors’ 4 and 6 were prepared and three of the unsymmetrical type, 8, 10, and 11. Glucosylation of symmetrical ‘acceptor’ 4 gave a higher yield of trisaccharide (44%) than protect ve-group manipulation, namely via selective debenzylidenation 2 9 or monoacetylation 2 5 which proceeded in moderate yields (33–34%). A comparison of catalysts in the cis-glucosylation

  两个对称的海藻糖的糖基“受体” 4和6中制备和三个非对称型的，8，10，和11。对称的“受体” 4的糖基化比保护ve-基团操纵（即通过选择性脱苄基2 9或单乙酰化2 5）获得的三糖收率更高（44％），中等收率（33-34％）。海藻糖“受体” 10与四-O-苄基-β-D-吡喃葡萄糖基氟13的顺式-葡萄糖基化反应中催化剂的比较异三氟甲磺酸酐（（Tf）2 O）作为新的反应性启动子，产生92％的三糖14，解封得到目标糖α-D-吡喃葡萄糖基-（1 4）-α，α-D-海藻糖。对大多数化合物的1 H-NMR光谱进行了广泛的分析。提倡使用ID TOCSY技术的时间效率，如果需要的话还可以通过ROESY实验进行补充。