benzyl laminaribioside | 71239-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl laminaribioside
• 英文别名: 1-(benzyl)-β-D-glucopyranosyl(1→3)-β-D-glucopyranoside；Benzyl-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosid；benzyl β-D-glucopyranosyl-(1->3)-β-D-glucopyranoside；benzyl β-D-Glcp-(1->3)-β-D-Glcp；Glc(b1-3)Glc(b)-O-Bn；(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 71239-02-6
• 化学式: C₁₉H₂₈O₁₁
• 分子量: 432.425
• InChiKey: MRWPZRCMSORCDQ-IDDMUUAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzyl laminaribioside 、 α-lactosyl fluoride 在 phosphate buffer 、 Cel₇B Glu₁₉₇Ala mutant 作用下， 反应 6.0h， 以100%的产率得到benzyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-β-D-gloucopyranosyl-(1->3)-β-D-glucopyranoside
  参考文献：
  名称：

  使用突变纤维素酶高效合成 β(1 → 4)-寡糖和多糖

  摘要：

  本报告描述了多种区域选择性修饰的 β(1→4)-寡糖和多糖的有效化学酶法合成。这种成功的方法基于：(i) 使用“糖合酶”，它是来自 Humicola insolens 的保留纤维素酶内切葡聚糖酶 I (Cel7B) 的 Glu-197-Ala 亲核突变体和 (ii) 修饰受体的合理设计和通过仔细检查野生型酶和突变酶的 X 射线结构给出的信息来确定供体分子。该突变体能够以高产率催化未取代和被各种单糖和二糖受体修饰的 α-糖二糖基氟的区域和立体选择性糖基化，以及通过单步反转机制聚合这些供体。

  DOI：

  10.1021/ja9936520
• 作为产物：
  描述：

  1-benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1→3)-2,4,6-tri-O-acetyl-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.92h， 以98%的产率得到benzyl laminaribioside
  参考文献：
  名称：

  衍生自β-（1,3）-d-葡聚糖的O-和C-糖苷的合成

  摘要：

  合成了一系列β-（1,3）-d-葡聚糖，这些结构特别在低聚物的还原端结合了结构变异。衍生自二糖和三糖的O-和C-糖苷均以良好的总收率和完全的选择性获得。O-糖苷是通过经典的Koenigs-Knorr糖基化获得的，而相应的C-糖苷是通过异头碳的烯丙基化和进一步的交叉复分解反应而获得的。最后，针对两种糖苷酶和两种内切葡聚糖酶评估了该化合物，未观察到抑制活性。

  DOI：

  10.1016/j.carres.2013.07.007

文献信息

• Engineering of glucoside acceptors for the regioselective synthesis of β-(1→3)-disaccharides with glycosynthases
  作者：Zsuzanna Marton、Vinh Tran、Charles Tellier、Michel Dion、Jullien Drone、Claude Rabiller

  DOI：10.1016/j.carres.2008.07.018

  日期：2008.11

  Glycosynthase mutants obtained from Thermotoga maritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1 -> 3)-beta-D-Glcp and aryl beta-D-Glcp-(1 -> 3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-D-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-D-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1 -> 3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively. (C) 2008 Elsevier Ltd. All rights reserved.
• Highly Efficient Synthesis of β(1 → 4)-Oligo- and -Polysaccharides Using a Mutant Cellulase
  作者：Sébastien Fort、Viviane Boyer、Lionel Greffe、Gideon J. Davies、Olga Moroz、Lars Christiansen、Martin Schülein、Sylvain Cottaz、Hugues Driguez

  DOI：10.1021/ja9936520

  日期：2000.6.1

  This report describes an efficient chemoenzymatic synthesis of a variety of regioselectively modified β(1→4)-oligo- and -polysaccharides. This successful approach was based on: (i) the use of a “glycosynthase” which is a Glu-197-Ala nucleophile mutant of the retaining cellulase endoglucanase I (Cel7B) from Humicola insolens and (ii) the rational design of modified acceptor and donor molecules through

  本报告描述了多种区域选择性修饰的 β(1→4)-寡糖和多糖的有效化学酶法合成。这种成功的方法基于：(i) 使用“糖合酶”，它是来自 Humicola insolens 的保留纤维素酶内切葡聚糖酶 I (Cel7B) 的 Glu-197-Ala 亲核突变体和 (ii) 修饰受体的合理设计和通过仔细检查野生型酶和突变酶的 X 射线结构给出的信息来确定供体分子。该突变体能够以高产率催化未取代和被各种单糖和二糖受体修饰的 α-糖二糖基氟的区域和立体选择性糖基化，以及通过单步反转机制聚合这些供体。
• Synthesis of O- and C-glycosides derived from β-(1,3)-d-glucans
  作者：Eduardo Marca、Jessika Valero-Gonzalez、Ignacio Delso、Tomás Tejero、Ramon Hurtado-Guerrero、Pedro Merino

  DOI：10.1016/j.carres.2013.07.007

  日期：2013.12

  A series of β-(1,3)-d-glucans have been synthesized incorporating structural variations specifically on the reducing end of the oligomers. Both O- and C-glucosides derived from di- and trisaccharides have been obtained in good overall yields and with complete selectivity. Whereas the O-glycosides were obtained via a classical Koenigs-Knorr glycosylation, the corresponding C-glycosides were obtained

  合成了一系列β-（1,3）-d-葡聚糖，这些结构特别在低聚物的还原端结合了结构变异。衍生自二糖和三糖的O-和C-糖苷均以良好的总收率和完全的选择性获得。O-糖苷是通过经典的Koenigs-Knorr糖基化获得的，而相应的C-糖苷是通过异头碳的烯丙基化和进一步的交叉复分解反应而获得的。最后，针对两种糖苷酶和两种内切葡聚糖酶评估了该化合物，未观察到抑制活性。