(2R,3S,4S,5R,6R)-2-(羟基甲基)-6-[(2R,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基四氢吡喃-3,4,5-三醇 | 34627-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2R,3S,4S,5R,6R)-2-(羟基甲基)-6-[(2R,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基四氢吡喃-3,4,5-三醇
• 英文名称: α-D-glucopyranosyl α-D-xylopyranoside
• 英文别名: α-D-Glucopyranosyl-α-D-xylopyranosid；alpha-Glucopyranosyl alpha-xylopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-3,4,5-triol
• CAS: 34627-06-0
• 化学式: C₁₁H₂₀O₁₀
• 分子量: 312.274
• InChiKey: FWHMSYJZNKVPEG-DRWRGJIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以95%的产率得到(2R,3S,4S,5R,6R)-2-(羟基甲基)-6-[(2R,3R,4S,5R)-3,4,5-三羟基四氢吡喃-2-基]氧基四氢吡喃-3,4,5-三醇
  参考文献：
  名称：

  Formation of 1,1-α,α-Glycosidic Bonds By Intramolecular Aglycone Delivery. A Convergent Synthesis of Trehalose

  摘要：

  [GRAPHICS]We report a new synthesis of trehalose analogs that involves the use of intramolecular aglycone delivery for stereoselective formation of the 1,1-alpha,alpha-glycosidic bond. The glycosylation reaction afforded the desired isomer exclusively and in good yield.

  DOI：

  10.1021/ol034836t

文献信息

• Anomeric Selectivity of Trehalose Transferase with Rare <scp>l</scp>-Sugars
  作者：Luuk Mestrom、Stefan R. Marsden、Hessel van der Eijk、Jesper U. Laustsen、Cy M. Jeffries、Dmitri I. Svergun、Peter-Leon Hagedoorn、Isabel Bento、Ulf Hanefeld

  DOI：10.1021/acscatal.0c02117

  日期：2020.8.7

  glycosyltransferases catalyze the formation of glycosidic bonds between nucleotide sugar donors and carbohydrate acceptors. The anomeric selectivity of trehalose transferase from Thermoproteus uzoniensis was investigated for both d- and l-glycopyranose acceptors. The enzyme couples a wide range of carbohydrates, yielding trehalose analogues with conversion and enantioselectivity of >98%. The anomeric selectivity inverts

  保留LeLoir糖基转移酶可催化核苷酸糖供体和碳水化合物受体之间糖苷键的形成。研究了对于d-和l- glycopyranose受体，来自uzoniensis的Thermoproteus uzoniensis的海藻糖转移酶的异头选择性。该酶偶联多种碳水化合物，产生海藻糖类似物，其转化率和对映选择性> 98％。从α异头选择性反转，α-（1→1） -糖苷键d -glycopyranose受体到α，β-（1→1） -糖苷键为升-glycopyranose受体，而（小号两种糖受体的选择性都保留下来。比较海藻糖转移酶与α，α-海藻糖和非天然α，β-海藻糖类似物的蛋白质晶体结构，突出了观察到的异头选择性逆转的机理。
• Catalytic versatility of trehalase: Synthesis of α-d-glucopyranosyl α-d-xylopyranoside from β-d-glucosyl fluoride and α-d-xylose
  作者：Takafumi Kasumi、Curtis F. Brewer、Elwyn T. Reese、Edward J. Hehre

  DOI：10.1016/0008-6215(86)85022-4

  日期：1986.1

  uniquely effective in enabling Trichoderma reesei trehalase to catalyze reactions with beta-D-glucosyl fluoride. As little as 0.2mM added alpha-D-glucose (0.4mM alpha-D-xylose) substantially increased the rate of enzymically catalyzed release of fluoride from 25mM beta-D-glucosyl fluoride at 0 degrees. Digests of beta-D-glucosyl fluoride plus alpha-D-xylose yielded the alpha, alpha-trehalose analog, alpha-D-glucopyranosyl

  先前显示海藻糖酶（参见参考文献5）水解α-D-葡萄糖基氟，形成β-D-葡萄糖，并由β-D-葡萄糖基氟加α-D-葡萄糖合成α，α-海藻糖。目前的观察结果进一步定义了在利用这些非糖苷底物时酶对单独的共底物的要求。发现α-D-葡糖醛糖和α-D-木吡喃糖在使里氏木霉海藻糖酶催化与β-D-葡糖基氟化物的反应方面具有独特的功效。添加低至0.2mM的α-D-葡萄糖（0.4mMα-D-木糖）在0度下大大提高了25mMβ-D-葡萄糖基氟化物的酶催化氟化物释放速率。β-D-葡萄糖基氟化物加α-D-木糖的消化物产生了α-α-海藻糖类似物，α-D-吡喃葡萄糖基α-D-木吡喃糖苷，作为一种短暂的（即随后水解的）转移产物。当β-D-葡糖基氟化物是供体时，需要具有轴向1-OH基的醛基吡喃糖受体，而当α-D-葡糖基氟化物是底物时需要水，这表明海藻糖的催化基团具有催化的灵活性。不同的立体化学反应。
• Compositions for improving the health and appearance of skin
  申请人：Algenist Holdings, Inc.

  公开号：US10231907B2

  公开（公告）日：2019-03-19

  Provided herein are microalgal skin care compositions and methods of improving the health and appearance of skin. Also provided are methods of using polysaccharides for applications such as topical personal care products, cosmetics, and wrinkle reduction compositions. The invention also provides novel decolorized microalgal compositions useful for improving the health and appearance of skin. The invention also includes insoluble polysaccharide particles for application to human skin.

  本文提供了微藻护肤组合物以及改善皮肤健康和外观的方法。还提供了将多糖用于局部个人护理产品、化妆品和除皱组合物等应用的方法。本发明还提供了用于改善皮肤健康和外观的新型脱色微藻组合物。本发明还包括用于人体皮肤的不溶性多糖颗粒。
• Synthesis and Glycosylation Shift of 1,1'-Disaccharides.
  作者：Mugio NISHIZAWA、Shinichi KODAMA、Yoshie YAMANE、Kiyoko KAYANO、Susumi HATAKEYAMA、Hidetoshi YAMADA

  DOI：10.1248/cpb.42.982

  日期：——

  Nineteen kinds of nonreducing 1,1'-disaccharides have synthesized by modified Koenigs-Knorr method, and characterized by NMR. The glycosylation shift of each anomeric carbon has been estimated.
• MICROALGAE-DERIVED COMPOSITIONS FOR IMPROVING THE HEALTH AND APPEARANCE OF SKIN
  申请人：TerraVia Holdings, Inc.

  公开号：EP1986665B1

  公开（公告）日：2018-05-02