gentiopentaose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: gentiopentaose
• 英文别名: 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-(hydroxymethyl)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: C₃₀H₅₂O₂₆
• 分子量: 828.727
• InChiKey: JKJNEIZIUZSCIE-KTIODWQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.2
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  427
• 氢给体数：
  17
• 氢受体数：
  26

反应信息

• 作为产物：
  描述：

  6-O-[1-[O-β-(2,3,4-tri-O-benzoyl)-D-glucopranosyl]₃-O-β-(2,3,4,6-tetra-O-benzoyl)-D-glucopranosyl]-D-glucopyranose 2,3,4-tri-O-benzoate 在 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到gentiopentaose
  参考文献：
  名称：

  [EN] ß-1,6-GLUCAN TRASTUZUMAB ANTIBODY CONJUGATES
  [FR] CONJUGUÉS D'ANTICORPS DE TRASTUZUMAB SS-1,6-GLUCANE

  摘要：

  本发明涵盖了将曲妥珠单抗或相关的曲妥珠抗体与β-1,6-葡聚糖寡聚体结合的实施方式。因此，本发明包括了包含曲妥珠与一个或多个β-1,6-葡聚糖寡聚体结合的组合物等内容。本发明还包括了制备和/或使用这种β-1,6-葡聚糖共轭物的方法等内容。在某些实施方式中，本发明的β-1,6-葡聚糖共轭物可用作治疗或治疗方法。

  公开号：

  WO2018106644A1

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.
• BETA-1,6-GLUCAN CETUXIMAB ANTIBODY CONJUGATES
  申请人：ImmuneXcite, Inc.

  公开号：US20180154014A1

  公开（公告）日：2018-06-07

  The present invention encompasses embodiments in which cetuximab or a related cetuximab antibody is conjugated to β-1,6-glucan oligomers. Thus, the present invention includes, among other things, compositions including cetuximab conjugated to one or more β-1,6-glucan oligomers. The present invention further includes, among other things, methods of making and/or using such β-1,6-glucan conjugates. In certain embodiments, a β-1,6-glucan conjugate of the present invention is useful as a therapeutic or in a method of therapy.
• [EN] ß-1,6-GLUCAN TRASTUZUMAB ANTIBODY CONJUGATES<br/>[FR] CONJUGUÉS D'ANTICORPS DE TRASTUZUMAB SS-1,6-GLUCANE
  申请人：INNATE BIOTHERAPEUTICS LLC

  公开号：WO2018106644A1

  公开（公告）日：2018-06-14

  The present invention encompasses embodiments in which trastuzumab or a related trastuzumab antibody is conjugated to β-1,6-glucan oligomers. Thus, the present invention includes, among other things, compositions including trastuzumab conjugated to one or more β-1,6-glucan oligomers. The present invention further includes, among other things, methods of making and/or using such β-1,6-glucan conjugates. In certain embodiments, a β-1,6-glucan conjugate of the present invention is useful as a therapeutic or in a method of therapy.

  本发明涵盖了将曲妥珠单抗或相关的曲妥珠抗体与β-1,6-葡聚糖寡聚体结合的实施方式。因此，本发明包括了包含曲妥珠与一个或多个β-1,6-葡聚糖寡聚体结合的组合物等内容。本发明还包括了制备和/或使用这种β-1,6-葡聚糖共轭物的方法等内容。在某些实施方式中，本发明的β-1,6-葡聚糖共轭物可用作治疗或治疗方法。