phenyl 1-thio-α-cellobioside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 1-thio-α-cellobioside
• 英文别名: α-thiophenyl cellobioside；Cel-α-SPh；Glc(b1-4)Glc(a)-SPh；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₈H₂₆O₁₀S
• 分子量: 434.464
• InChiKey: FGJLUHTXBRGPSV-LTHBGAKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  195
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4,6-dimethoxy-1,3,5-triazin-2-yl β-lactoside 、 phenyl 1-thio-α-cellobioside 在 endo-β-glucanase III (EGIII) from Trichoderma reesei 作用下， 以95%的产率得到phenyl 1-thio-4-O-(4-O-(4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranosyl)-beta-D-glucopyranosyl)-alpha-D-glucopyranoside
  参考文献：
  名称：

  用于化学酶促寡糖合成的新型糖基供体：4,6-二甲氧基-1,3,5-三嗪-2-基糖苷。

  摘要：

  一种新型活化的糖苷化合物4,6-二甲氧基-1,3,5-三嗪-2-基β-乳糖苷（DMT-β-Lac）可以直接由水中的乳糖制备，而无需使用任何保护基。被发现是一种有效的糖基供体，用于内切1,4-β-葡聚糖酶催化的酶促糖基化。

  DOI：

  10.1039/b801090k
• 作为产物：
  描述：

  纤维素二糖 、 苯硫酚 在 三氟乙酸 作用下， 反应 168.0h， 生成 phenyl 1-thio-α-cellobioside
  参考文献：
  名称：

  Stereoselective 1,2-CIS-1-Thioglycosidation of Aldohexoses withTert-Butyl Mercaptan in 90% Trifluoroacetic Acid

  摘要：

  tert-Butyl 1,2-cis-1-thioglycopyranosides of various aldohexoses (D-glucose, D-galactose, D-mannose, and L-rhamnose), and disaccharides (cellobiose, lactose, and maltose) were preferentially prepared in good yields by reacting the corresponding free sugars with tert-butyl mercaptan in 90% trifluoroacetic acid at room temperature. No selectivity, however, was ob served at all in the case of 2-deoxy-D-arabino-hexopyranose. A possible mechanism for the 1,2-cis-selectivity was discussed from a standpoint of thermodynamic and kinetic control.

  DOI：

  10.1080/07328300008544064

文献信息

• Novel dialkoxytriazine-type glycosyl donors for cellulase-catalysed lactosylation
  作者：Tomonari Tanaka、Masato Noguchi、Kazuhito Watanabe、Takuya Misawa、Masaki Ishihara、Atsushi Kobayashi、Shin-ichiro Shoda

  DOI：10.1039/c0ob00190b

  日期：——

  Novel glycosidic compounds, 4,6-dialkoxy-1,3,5-triazin-2-yl β-lactosides (DAT-β-Lac), have been prepared directly in water from lactose. The reaction was carried out on a laboratory scale without protecting the hydroxy groups of lactose. The resulting triazine derivatives were found to be recognized by endo-β1,4-glucanase III from Trichoderma reesei (EGIII). The EGIII-catalysed transglycosylation of 4,6-dimethoxy-1,3,5-triazine derivative (DMT-β-Lac) with various glycosyl acceptors has successfully been demonstrated, affording the corresponding lactosylated products.

  新型糖苷化合物，即4,6-二烷氧基-1,3,5-三嗪-2-基 β-乳糖苷（DAT-β-Lac），已直接在水中从乳糖制备。该反应在实验室规模进行，无需保护乳糖的羟基。所得的三嗪衍生物被发现能被来自里氏木霉（Trichoderma reesei）的内切-β1,4- glucanase III（EGIII）识别。EGIII催化的4,6-二甲氧基-1,3,5-三嗪衍生物（DMT-β-Lac）与各种糖基受体的转糖苷作用已成功展示，得到了相应的乳糖基化产物。