O-α-D-glucopyranosyl-(1<*>6)-O-α-D-glucopyranosyl-(1<*>3)-D-glucopyranose | 21291-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-α-D-glucopyranosyl-(1<*>6)-O-α-D-glucopyranosyl-(1<*>3)-D-glucopyranose
• 英文别名: α-isomaltosyl-(1->3)-glucose；panose；3α-Isomaltosyl-glucose；Glc(a1-6)Glc(a1-3)Glc；(3R,4S,5R,6R)-6-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxane-2,3,5-triol
• CAS: 21291-02-1
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: QNWHPAQNSLSGBO-WUBZUXIOSA-N

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

• 作为反应物：
  描述：

  O-α-D-glucopyranosyl-(1<*>6)-O-α-D-glucopyranosyl-(1<*>3)-D-glucopyranose 在 cycloalternan-degrading enzyme 作用下， 生成 D-葡萄糖 、 D-isomaltose
  参考文献：
  名称：

  Purification and characterization of an intracellular cycloalternan-degrading enzyme from Bacillus sp. NRRL B-21195

  摘要：

  A novel intracellular cycloalternan-degrading enzyme (CADE) was purified to homogeneity from the cell pellet of Bacillus sp. NRRL B-21195. The enzyme has a molecular mass of 125 kDa on SDS-PAGE. The pH optimum was 7.0. and the enzyme was stable from pH 6.0 to 9.2. The temperature optimum was 35degreesC and the enzyme exhibited stability up to 50degreesC. The enzyme hydrolyzed cycloalternan [CA; cyclo{--> 6)-alpha-D-Glcp-(1 --> 3)-alpha-D-Glcp-(1-->6)-alpha-D-Glcp-(-->3)alpha-D-Glcp-(1-->}] as the best substrate. to produce only isomaltose via an intermediate, alpha-isomaltosyl-(l --> 3)-isomaltose. This enzyme also hydrolyzed isomaltosyl substrates. such as panose, alpha-isomaltosyl-(1-->4)-maltooligosaccharides, alpha-isomaltosyl-(1-->3)-glucose, and alpha-isomaltosyl-(1 --> 3)-isomaltose to liberate isomaltose. Neither maltooligosaccharides nor isomaltooligosaccharides were hydrolyzed by the enzyme, indicating that CADE requires alpha-isomaltosyl residues connected with (1-->4)- or (1-->3)-linkages. The K-m value of cycloalternan (1.68 mM) was 20% of that of panose (8.23 mM). The k(cat) value on panose (14.4 s(-1)) was not significantly different from that of cycloalternan (10.8s(-1)). Judging from its specificity, the systematic name of the enzyme should be cycloalternan isomaltosylhydrolase. This intracellular enzyme is apparently involved in the metabolism of starch via cycloalternan in Bacillus sp. NRRL B-21195. its role being to hydrolyze cycloalternan inside the cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.02.008
• 作为产物：
  描述：

  benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>3)-2,4,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以66%的产率得到O-α-D-glucopyranosyl-(1<*>6)-O-α-D-glucopyranosyl-(1<*>3)-D-glucopyranose
  参考文献：
  名称：

  使用葡萄糖二糖和乳糖的七苄基衍生物进行脱水糖基化

  摘要：

  D-吡喃葡萄糖的 2-、3-、4-和 6-OH 基团与葡萄糖二糖的七-O-苄基衍生物的脱水糖基化（OD-吡喃葡萄糖基-（1→n）-D-吡喃葡萄糖；n = 2， 3、4 或 6) 和乳糖，在对硝基苯磺酰氯、三氟甲磺酸银和三乙胺的三元混合物在二氯甲烷中的存在下表明反应的选择性取决于异头构型和与还原三苄基葡萄糖的连接位置非还原性四苄基葡萄糖残基的部分和要糖基化的 OH 基团的类别。使用对硝基苯磺酰氯、三氟甲磺酸银、N,N-二甲基乙酰胺和三乙胺的四元混合物使除 β(1→2)-连接的生物基供体以外的所有物质都发生 α-缩合。

  DOI：

  10.1246/bcsj.65.3257

文献信息

• Dehydrative Glycosylation Using Heptabenzyl Derivatives of Glucobioses and Lactose
  作者：Shinkiti Koto、Naohiko Morishima、Sonoko Shichi、Hisamitsu Haigoh、Motoko Hirooka、Mitsuko Okamoto、Takashi Higuchi、Koichi Shimizu、Yosuke Hashimoto、Terumi Irisawa、Hidehiro Kawasaki、Yasushi Takahashi、Masayo Yamazaki、Yoko Mori、Keiko Kudo、Takako Ikegaki、Sonoe Suzuki、Shonosuke Zen

  DOI：10.1246/bcsj.65.3257

  日期：1992.12

  reducing tribenzylglucose moiety of the nonreducing tetrabenzylglucosyl residue and on the class of the OH group to be glycosylated. The use of a quaternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine made all but the β(1→2)-linked biosyl donor undergo α-condensation. Several new linear trisaccharides were obtained via debenzylation

  D-吡喃葡萄糖的 2-、3-、4-和 6-OH 基团与葡萄糖二糖的七-O-苄基衍生物的脱水糖基化（OD-吡喃葡萄糖基-（1→n）-D-吡喃葡萄糖；n = 2， 3、4 或 6) 和乳糖，在对硝基苯磺酰氯、三氟甲磺酸银和三乙胺的三元混合物在二氯甲烷中的存在下表明反应的选择性取决于异头构型和与还原三苄基葡萄糖的连接位置非还原性四苄基葡萄糖残基的部分和要糖基化的 OH 基团的类别。使用对硝基苯磺酰氯、三氟甲磺酸银、N,N-二甲基乙酰胺和三乙胺的四元混合物使除 β(1→2)-连接的生物基供体以外的所有物质都发生 α-缩合。
• Purification and characterization of an intracellular cycloalternan-degrading enzyme from Bacillus sp. NRRL B-21195
  作者：Yeon-Kye Kim、Motomitsu Kitaoka、Kiyoshi Hayashi、Cheorl-Ho Kim、Gregory L. Côté

  DOI：10.1016/j.carres.2004.02.008

  日期：2004.4

  A novel intracellular cycloalternan-degrading enzyme (CADE) was purified to homogeneity from the cell pellet of Bacillus sp. NRRL B-21195. The enzyme has a molecular mass of 125 kDa on SDS-PAGE. The pH optimum was 7.0. and the enzyme was stable from pH 6.0 to 9.2. The temperature optimum was 35degreesC and the enzyme exhibited stability up to 50degreesC. The enzyme hydrolyzed cycloalternan [CA; cyclo--> 6)-alpha-D-Glcp-(1 --> 3)-alpha-D-Glcp-(1-->6)-alpha-D-Glcp-(-->3)alpha-D-Glcp-(1-->}] as the best substrate. to produce only isomaltose via an intermediate, alpha-isomaltosyl-(l --> 3)-isomaltose. This enzyme also hydrolyzed isomaltosyl substrates. such as panose, alpha-isomaltosyl-(1-->4)-maltooligosaccharides, alpha-isomaltosyl-(1-->3)-glucose, and alpha-isomaltosyl-(1 --> 3)-isomaltose to liberate isomaltose. Neither maltooligosaccharides nor isomaltooligosaccharides were hydrolyzed by the enzyme, indicating that CADE requires alpha-isomaltosyl residues connected with (1-->4)- or (1-->3)-linkages. The K-m value of cycloalternan (1.68 mM) was 20% of that of panose (8.23 mM). The k(cat) value on panose (14.4 s(-1)) was not significantly different from that of cycloalternan (10.8s(-1)). Judging from its specificity, the systematic name of the enzyme should be cycloalternan isomaltosylhydrolase. This intracellular enzyme is apparently involved in the metabolism of starch via cycloalternan in Bacillus sp. NRRL B-21195. its role being to hydrolyze cycloalternan inside the cells. (C) 2004 Elsevier Ltd. All rights reserved.