gentiotetraose | 27575-68-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: gentiotetraose
• 英文别名: Glc(b1-6)Glc(b1-6)Glc(b1-6)Glc；(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-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• CAS: 27575-68-4
• 化学式: C₂₄H₄₂O₂₁
• 分子量: 666.585
• InChiKey: DFKPJBWUFOESDV-RQRPBDKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  348
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-D-glucopyranose 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以78%的产率得到gentiotetraose
  参考文献：
  名称：

  轻松有效地合成α-（1→6）连接的甘露糖二糖，三糖，四糖，六糖，八糖和十二糖以及β-（1→6）连接的葡萄糖二糖，三糖糖，三糖，四糖，六糖和八糖，使用三氯乙酰亚氨酸糖作为供体，未保护或部分保护的糖苷作为受体

  摘要：

  摘要在TMSOTf存在下，2,3,4,6-四-O-乙酰基-α-d-甘露吡喃糖基三氯亚氨基酸酯与烯丙基α-d-甘露吡喃糖苷选择性地产生2,3,4,6-四-O-烯丙基通过原酸酯中间体形成乙酰基-α-d-甘露吡喃糖基-（1→6）-α-d-甘露吡喃糖苷。3的苯甲酰化，然后脱醛，然后三氯酰亚胺化，得到二糖供体2,3,4,6-四-O-乙酰基-α-d-甘露吡喃糖基-（1→6）-2,3,4-三-O -苯甲酰基-α-d-甘露吡喃糖基三氯亚氨酸酯，而3的苯甲酰化，然后选择性除去乙酰基，则产生二糖受体烯丙基α-d-甘露糖吡喃糖基-（1→6）-2,3,4-三-O-苯甲酰基- α-d-甘露吡喃糖苷。5与6偶合得到四糖烯丙基2,3,4,6-四-O-乙酰基-α-d-甘露吡喃糖基-（1→6）-2,3,4-三-O-苯甲酰基-α-d -甘露吡喃糖基-（1→6）-α-d-甘露吡喃糖基-（1→6）-2，3,4-三-O-苯甲酰基-α-d-甘露吡喃糖苷，转化为四糖供体2

  DOI：

  10.1016/s0008-6215(01)00070-2

文献信息

• Enzymatic synthesis of gentiooligosaccharides by transglycosylation with β-glycosidases from Penicillium multicolor
  作者：Yoshinori Fujimoto、Takeshi Hattori、Shuji Uno、Takeomi Murata、Taichi Usui

  DOI：10.1016/j.carres.2009.03.006

  日期：2009.5

  A crude enzyme preparation from Penicillium multicolor efficiently produced mainly gentiotriose to gentiopentaose (d.p. 3-5) by transglycosylation using a high concentration of gentiobiose as the substrate. The resulting gentiotriose was examined in a gustatory sensation test using human volunteers, and was determined to have one-fifth of the bitterness of gentiobiose. The crude enzyme preparation was analyzed by chromatography to determine the enzyme responsible for formation of the gentiooligosaccharides. The transglycosylation was shown to take place in two stages by a combination of beta-glucosidase and beta-(1 -> 6)-glucanase. In the initial stage, which was the rate-limiting step in the overall process, beta-glucosidase produced mainly gentiotriose from gentiobiose. In the second step, beta-(1 -> 6)-glucanase acted on the resulting gentiotriose, which served as both donor and acceptor, to produce a series of gentiooligosaccharides (d.p. 4-9) by transglycosylation. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.
• A facile and effective synthesis of α-(1→6)-linked mannose di-, tri-, tetra-, hexa-, octa-, and dodecasaccharides, and β-(1→6)-linked glucose di-, tri-, tetra-, hexa-, and octasaccharides using sugar trichloroacetimidates as the donors and unprotected or partially protected glycosides as the acceptors
  作者：Yuliang Zhu、Fanzuo Kong

  DOI：10.1016/s0008-6215(01)00070-2

  日期：2001.5

  coupling of 12 with the octasaccharide acceptor 20 . Similar strategies were used for the syntheses of β-(1→6)-linked glucose di-, tri-, tetra-, hexa-, and octamers. Deprotection of the oligosaccharides in ammonia-saturated methanol yielded the free α-(1→6)-linked mannosyl and β-(1→6)-linked glucosyl oligomers.

  摘要在TMSOTf存在下，2,3,4,6-四-O-乙酰基-α-d-甘露吡喃糖基三氯亚氨基酸酯与烯丙基α-d-甘露吡喃糖苷选择性地产生2,3,4,6-四-O-烯丙基通过原酸酯中间体形成乙酰基-α-d-甘露吡喃糖基-（1→6）-α-d-甘露吡喃糖苷。3的苯甲酰化，然后脱醛，然后三氯酰亚胺化，得到二糖供体2,3,4,6-四-O-乙酰基-α-d-甘露吡喃糖基-（1→6）-2,3,4-三-O -苯甲酰基-α-d-甘露吡喃糖基三氯亚氨酸酯，而3的苯甲酰化，然后选择性除去乙酰基，则产生二糖受体烯丙基α-d-甘露糖吡喃糖基-（1→6）-2,3,4-三-O-苯甲酰基- α-d-甘露吡喃糖苷。5与6偶合得到四糖烯丙基2,3,4,6-四-O-乙酰基-α-d-甘露吡喃糖基-（1→6）-2,3,4-三-O-苯甲酰基-α-d -甘露吡喃糖基-（1→6）-α-d-甘露吡喃糖基-（1→6）-2，3,4-三-O-苯甲酰基-α-d-甘露吡喃糖苷，转化为四糖供体2