phenyl β-D-galactopyranosyl-(1->3)-1-thio-β-D-glucopyranoside | 210281-92-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl β-D-galactopyranosyl-(1->3)-1-thio-β-D-glucopyranoside
• 英文别名: phenyl β-D-galactopyranosyl-(1→3)-1-thio-β-D-glucopyranoside；phenyl β-D-Galp-(1->3)-1-thio-β-D-Glcp
• CAS: 210281-92-8
• 化学式: C₁₈H₂₆O₁₀S
• 分子量: 434.464
• InChiKey: ONYQBPMRXSLRTF-RLJCQIFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  169.3
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  phenyl β-D-galactopyranosyl-(1->3)-1-thio-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 为溶剂， 反应 0.5h， 生成 β-D-Galp-(1→3)-β-D-Glcp 、 β-D-galactopyranosyl-(1->3)-α-D-glucopyranoside
  参考文献：
  名称：

  Engineering of glucoside acceptors for the regioselective synthesis of β-(1→3)-disaccharides with glycosynthases

  摘要：

  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.

  DOI：

  10.1016/j.carres.2008.07.018
• 作为产物：
  描述：

  1,2,3,4,6-D-葡萄糖五乙酸酯 在 吡啶 、 甲醇 、 Thermus nonproteolyticus HG₁₀₂ E₃₃₈A mutant 、 氢氟酸 、 sodium methylate 、 聚甘氨酸 、 sodium hydroxide 作用下， 以 aq. buffer 为溶剂， 反应 48.0h， 生成 phenyl β-D-galactopyranosyl-(1->3)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  具有广泛底物特异性的糖合酶——构建寡糖文库的高效生物催化剂

  摘要：

  通过使用定点诱变从非蛋白水解栖热菌 β-糖苷酶 (TnG) 中开发出一种多功能糖合酶 (TnG-E338A)，其底物范围非常广泛。这种生物催化剂的实际效用已通过以高达 100% 的分离产率轻松生成包含各种寡糖和甾体糖苷（总共 25 种化合物）的小型文库得到证明。此外，该酶在一锅平行反应中很容易合成了一系列八种低聚糖，这突出了其在碳水化合物库的组合构建中的潜力，这将有助于糖组学和糖治疗研究。值得注意的是，该酶提供了一种可以将糖合酶技术扩展到组合化学的方法。

  DOI：

  10.1002/ejoc.201201507