[O-β-D-glucopyranosyl-1,6]₆-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [O-β-D-glucopyranosyl-1,6]₆-D-glucopyranoside
• 英文别名: gentioheptaose；Glc(b1-6)Glc(b1-6)Glc(b1-6)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-[[(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]oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• 化学式: C₄₂H₇₂O₃₆
• 分子量: 1153.01
• InChiKey: WZUUEWPIQJEOOV-URBNKUOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -15.5
• 重原子数：
  78
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  585
• 氢给体数：
  23
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  [O-β-D-glucopyranosyl-1,6]₆-D-glucopyranoside 在 sodium cyanoborohydride 作用下， 以 水 为溶剂， 反应 27.0h， 生成 [(2R,3R,4R,5RS)-2,3,4,5-tetrahydroxy-6-(N-methyl-N-(2-carboxymethyloxy))amino]hexyl [O-β-D-glucopyranosyl-1,6]₅-β-D-glucopyranoside
  参考文献：
  名称：

  Immunomodulating beta-1,6-D-glucans

  摘要：

  这项发明涉及对β-1,6-D-葡聚糖的修饰，例如，符合式（I）的结构，以及这些组合物调节免疫反应的能力。

  公开号：

  US10266609B2
• 作为产物：
  描述：

  gentiotriose 在 Penicillium multicolor IAM7153 β-(1->6)-glucanase 作用下， 以 sodium acetate buffer 为溶剂， 反应 24.0h， 以7.8%的产率得到gentiotetraose
  参考文献：
  名称：

  Enzymatic synthesis of gentiooligosaccharides by transglycosylation with β-glycosidases from Penicillium multicolor

  摘要：

  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.

  DOI：

  10.1016/j.carres.2009.03.006

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.
• 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.
• Immunomodulating beta-1,6-D-glucans
  申请人：Innate Biotherapeutics, LLC

  公开号：US10266609B2

  公开（公告）日：2019-04-23

  This invention relates to modifications of β-1,6-D-glucans, e.g., structures according to Formula (I), and the ability of these compositions to modulate an immune response.

  这项发明涉及对β-1,6-D-葡聚糖的修饰，例如，符合式（I）的结构，以及这些组合物调节免疫反应的能力。