gentiotriosyl | 52485-16-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: gentiotriosyl
• 英文别名: Gentiotriose；β-Gentiotriose；(2R,3R,4S,5S,6R)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl}oxan-2-yl]oxymethyl}oxane-2,3,4,5-tetrol；(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• CAS: 52485-16-2
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: FBJQEBRMDXPWNX-CFCQXFMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 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：

  gentiotriosyl 、 p-nitrophenyl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside 在 Penicillium multicolor LAM7153 β-(1→6)-glucanase 作用下， 以 aq. acetate buffer 为溶剂， 反应 116.0h， 以2.1%的产率得到
  参考文献：
  名称：

  Mode of action of a β-(1→6)-glucanase from Penicillium multicolor

  摘要：

  beta-(1 -> 6)-Glucanase from the culture filtrate of Penicillium multicolor LAM7153 was purified by ammonium sulfate precipitation, followed by cation-exchange and affinity chromatography using gentiotetraose (Gen(4)) as ligand. The hydrolytic mode of action of the purified protein on beta-(1 -> 6)-glucan (pustulan) was elucidated in real time during the reaction by HPAEC-PAD analysis. Gentiooligosaccharides (DP 2-9, Gen(2-9)), methyl beta-gentiooligosides (DP 2-6, Gen(2-6) beta-OMe), and p-nitrophenyl beta-gentiooligosides (DP 2-6, Gen(2-6) beta-pNP) were used as substrates to provide analytical insight into how the cleavage of pustulan (DP 320) is actually achieved by the enzyme. The enzyme was shown to completely hydrolyze pustulan in three steps as follows. In the initial stage, the enzyme quickly cleaved the glucan with a pattern resembling an endo-hydrolase to produce a short-chain glucan (DP 45) as an intermediate. In the midterm stage, the resulting short-chain glucan was further cleaved into two fractions corresponding to DP 15-7 and DP 2-4 with great regularity. In the final stage, the lower oligomers corresponding to DP 3 and DP 4 were very slowly hydrolyzed into glucose and gentiobiose (Gen(2)). As a result, the hydrolytic cooperation of both an endo-type and saccharifying-type reaction by a single enzyme, which plays a bifunctional role, led to complete hydrolysis of the glucan. Thus, beta-(1 -> 6)-glucanase varies its mode of action depending on the chain length derived from the glucan. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.11.002
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以9.5 mg的产率得到gentiotriosyl
  参考文献：
  名称：

  组合离子捕获和释放寡糖合成（combi-ICROS）。

  摘要：

  报导了组合的离子液体支持的“捕获和释放”策略，用于寡糖合成（combi-ICROS）。在一个锅中合成了一系列β-（1-> 6）葡聚糖二糖，三糖和四糖，以展示该策略的多功能性。

  DOI：

  10.1039/c2cc37164b

文献信息

• Mode of action of a β-(1→6)-glucanase from Penicillium multicolor
  作者：Takeshi Hattori、Yasuna Kato、Shuji Uno、Taichi Usui

  DOI：10.1016/j.carres.2012.11.002

  日期：2013.1

  beta-(1 -> 6)-Glucanase from the culture filtrate of Penicillium multicolor LAM7153 was purified by ammonium sulfate precipitation, followed by cation-exchange and affinity chromatography using gentiotetraose (Gen(4)) as ligand. The hydrolytic mode of action of the purified protein on beta-(1 -> 6)-glucan (pustulan) was elucidated in real time during the reaction by HPAEC-PAD analysis. Gentiooligosaccharides (DP 2-9, Gen(2-9)), methyl beta-gentiooligosides (DP 2-6, Gen(2-6) beta-OMe), and p-nitrophenyl beta-gentiooligosides (DP 2-6, Gen(2-6) beta-pNP) were used as substrates to provide analytical insight into how the cleavage of pustulan (DP 320) is actually achieved by the enzyme. The enzyme was shown to completely hydrolyze pustulan in three steps as follows. In the initial stage, the enzyme quickly cleaved the glucan with a pattern resembling an endo-hydrolase to produce a short-chain glucan (DP 45) as an intermediate. In the midterm stage, the resulting short-chain glucan was further cleaved into two fractions corresponding to DP 15-7 and DP 2-4 with great regularity. In the final stage, the lower oligomers corresponding to DP 3 and DP 4 were very slowly hydrolyzed into glucose and gentiobiose (Gen(2)). As a result, the hydrolytic cooperation of both an endo-type and saccharifying-type reaction by a single enzyme, which plays a bifunctional role, led to complete hydrolysis of the glucan. Thus, beta-(1 -> 6)-glucanase varies its mode of action depending on the chain length derived from the glucan. (C) 2012 Elsevier Ltd. All rights reserved.
• Combinatorial ionic catch-and-release oligosaccharide synthesis (combi-ICROS)
  作者：Imke Sittel、Anh-Tuan Tran、David Benito-Alifonso、M. Carmen Galan

  DOI：10.1039/c2cc37164b

  日期：——

  A combinatorial ionic-liquid-supported "catch-and-release" strategy for oligosaccharide synthesis (combi-ICROS) is reported. A series of beta-(1-->6) glucan di-, tri- and tetra-saccharides were synthesized in one pot to showcase the versatility of the strategy.

  报导了组合的离子液体支持的“捕获和释放”策略，用于寡糖合成（combi-ICROS）。在一个锅中合成了一系列β-（1-> 6）葡聚糖二糖，三糖和四糖，以展示该策略的多功能性。