gentiotriose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: gentiotriose
• 英文别名: 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-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: FBJQEBRMDXPWNX-GCVNLWEKSA-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：

  gentiotriose 在 Penicillium multicolor IAM₇₁₅₃ crude enzyme preparation 作用下， 以 sodium acetate buffer 为溶剂， 反应 25.0h， 生成 gentiotetraose 、 gentiopentaose
  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
• 作为产物：
  描述：

  Β-龙胆二糖 在 purified Trichoderma viride β-glucosidase 作用下， 反应 24.0h， 以20.2%的产率得到gentiotriose
  参考文献：
  名称：

  里氏木霉β-葡萄糖苷酶从β-葡萄糖酶产生的新三糖和四糖的区域选择性合成及其NMR谱的结构分析

  摘要：

  摘要从绿色木霉纤维素酶复合物中部分纯化了一种新的β-葡萄糖苷酶。该β-葡糖苷酶水解β-（1→2）-，β-（1→3）-，β-（1→4）-和β-（1→6）-连接的葡糖苷酶并催化纤维二糖的转糖基化反应。产生区域选择性的β-d -Glc-（1→6）-β-d-Glc-（1→4）-d -Glc（产率：18.8％）和β-d -Glc-（1→6）-β -d -Glc-（1→6）-β-d-Glc-（1→4）-d-Glc（3.7％）。此外，该酶将laminarabiose和龙胆二糖转化为β-d -Glc-（1→6）-β-d-Glc-（1→3）-d -Glc（15.3％）和β-d -Glc-（1→ 6）-β-d-Glc-（1→6）-d-Glc（20.2％）。产物的结构通过1 H和13 C NMR光谱确定。该酶显示的这种高区域选择性和立体选择性通常可用于寡糖合成。

  DOI：

  10.1016/s0008-6215(99)00166-4

文献信息

• Rapid oligosaccharide synthesis on a fluorous support
  作者：Kohtaro Goto、Tsuyoshi Miura、Daisuke Hosaka、Hiroharu Matsumoto、Mamoru Mizuno、Hide-ki Ishida、Toshiyuki Inazu

  DOI：10.1016/j.tet.2004.07.027

  日期：2004.9

  The novel fluorous support Hfb (hexakisfluorous chain-type butanoyl) was easily prepared. The Hfb group was readily introduced into the anomeric hydroxyl group of a carbohydrate, and was recyclable after cleavage. The use of the Hfb group was applicable for the rapid oligosaccharide synthesis in which the synthetic intermediates could be purified using fluorous and normal organic solvents. Each synthetic

  新型氟载体Hfb（六氟链型丁酰基）易于制备。的HFB组容易引入到异头羟基的碳水化合物的，并且是切割后可回收再利用。Hfb基团的使用适用于快速寡糖合成，其中合成中间体可以使用氟和普通有机溶剂进行纯化。每种合成中间体都可以通过TLC，NMR和质谱监测。
• 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。
• 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.
• Regioselective Syntheses of New Tri-and Tetrasaccharides by Transglycosylation of Trichoderma Viride β-Glucosidase
  作者：Hiroyuki Kono、Shin Kawano、Tomoki Erata、Mitsuo Takai

  DOI：10.1080/07328300008544070

  日期：2000.1

  A new beta-glucosidase, which was partially purified from Trichoderma viride cellulase, catalyzed a transglycosylation reaction of cellobiose to give beta-D-Glcp-(1-->6)beta-D-Glcp-(1 --> 4)-D-Glcp 1 and beta-D-Glcp-(1 --> 6)-beta-D-Glcp-(1 --> 6)-beta-D-Glcp-(1 --> 4)-D-Glcp 2, regioselectively. Furthermore, the enzyme converted laminaribiose and gentiobiose into beta-D-Glcp-(1 -->6)-beta-D-Glcp-(1 --> 3)-D-Glcp 3 and beta-o-Glcp-(1 --> 6)-beta-D-Glcp-(1 --> 6)-D-Glcp 4, respectively. Selective beta-(1-->6) transglycosylation was achieved.
• ANGIBLAUD, P.;BOSSO, C.;UTILLE, J. -P., CARBOHYDR. RES., 198,(1990) N, C. 403-407
  作者：ANGIBLAUD, P.、BOSSO, C.、UTILLE, J. -P.

  DOI：——

  日期：——