4,6-dimethoxy-1,3,5-triazin-2-yl β-lactoside | 1033330-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6-dimethoxy-1,3,5-triazin-2-yl β-lactoside
• 英文别名: 4,5-dimethoxy-1,3,5-triazin-2-yl β-lactoside；4,6-dimethoxy-1,3,5-triazin-2-yl β-D-lactoside；DMT-β-Lac；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-6-[(4,6-dimethoxy-1,3,5-triazin-2-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1033330-68-5
• 化学式: C₁₇H₂₇N₃O₁₃
• 分子量: 481.414
• InChiKey: LBFRIHYDEDHWLC-BYBSGSAKSA-N

物化性质

• 熔点：
  163 °C (decomp)
• 沸点：
  799.3±70.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  236
• 氢给体数：
  7
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4,6-dimethoxy-1,3,5-triazin-2-yl β-lactoside 、 苯基-BETA-葡萄糖吡喃糖苷 在 endo-β1,4-glucanase III from trichoderma reesei 作用下， 反应 1.0h， 以39%的产率得到Gal(b1-4)Glc(b1-4)Glc(b)-O-Ph
  参考文献：
  名称：

  Novel dialkoxytriazine-type glycosyl donors for cellulase-catalysed lactosylation

  摘要：

  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。

  DOI：

  10.1039/c0ob00190b
• 作为产物：
  描述：

  Lactose 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 在 2,6-二甲基吡啶 作用下， 以 水 为溶剂， 反应 18.0h， 以73%的产率得到4,6-dimethoxy-1,3,5-triazin-2-yl β-lactoside
  参考文献：
  名称：

  Novel dialkoxytriazine-type glycosyl donors for cellulase-catalysed lactosylation

  摘要：

  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。

  DOI：

  10.1039/c0ob00190b

文献信息

• One-pot chemoenzymatic synthesis of glycopolymers from unprotected sugars <i>via</i> glycosidase-catalysed glycosylation using triazinyl glycosides
  作者：Tomonari Tanaka、Ayane Matsuura、Yuji Aso、Hitomi Ohara

  DOI：10.1039/d0cc02838j

  日期：——

  Glycopolymers were successfully synthesised from unprotected sugars in aqueous media via a one-pot chemoenzymatic process of three reactions; the direct synthesis of 4,6-dimethoxy-1,3,5-triazin-2-yl glycosides from unprotected sugars, a glycosidase-catalysed glycosylation using the triazinyl glycoside to afford glycomonomers and a radical polymerisation. The resulting glycopolymers exhibited specific

  通过三个反应的一锅化学酶法，成功地在水性介质中由未保护的糖合成了糖共聚物。由未保护的糖直接合成4,6-二甲氧基-1,3,5-三嗪-2-基糖苷，使用三嗪基糖苷进行糖苷酶催化的糖基化反应以提供糖单体和自由基聚合。所得的糖聚合物表现出与相应的凝集素作为糖簇的特异性相互作用。
• A novel glycosyl donor for chemo-enzymatic oligosaccharide synthesis: 4,6-dimethoxy-1,3,5-triazin-2-yl glycoside
  作者：Tomonari Tanaka、Masato Noguchi、Atsushi Kobayashi、Shin-ichiro Shoda

  DOI：10.1039/b801090k

  日期：——

  compound, 4,6-dimethoxy-1,3,5-triazin-2-yl beta-lactoside (DMT-beta-Lac), which can be prepared directly from lactose in water without using any protecting groups, was found to be an efficient glycosyl donor for enzymatic glycosylation catalyzed by an endo-1,4-beta-glucanase.

  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。
• 4,6-Dimethoxy-1,3,5-triazine oligoxyloglucans: Novel one-step preparable substrates for studying action of endo-β-1,4-glucanase III from Trichoderma reesei
  作者：Atsushi Kobayashi、Tomonari Tanaka、Kazuhito Watanabe、Masaki Ishihara、Masato Noguchi、Hirofumi Okada、Yasushi Morikawa、Shin-ichiro Shoda

  DOI：10.1016/j.bmcl.2010.04.122

  日期：2010.6

  Two kinds of 4,6-dimethoxy-1,3,5-triazine (DMT) oligoxyloglucans, DMT-beta-XXXG and DMT-beta-XLLG, have been synthesized via one-step procedure starting from the corresponding unprotected oligoxyloglucans in water. The resulting DMT derivatives were found to be hydrolyzed by endo-beta-1,4-D-glucanase III from Trichoderma reesei (EGIII) and utilized as substrates for determination of the kinetic parameters of EGIII. The present DMT-method would be a convenient analytical tool for studying the action of glycosyl hydrolases due to the extremely simple synthetic process of DMT-glycosides without using protecting groups. (C) 2010 Elsevier Ltd. All rights reserved.
• 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。