2,5-dinitrophenyl β-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dinitrophenyl β-D-mannopyranoside
• 英文别名: 2,5-dinitrophenyl β-mannoside；(2S,3S,4S,5S,6R)-2-(2,5-dinitrophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₂H₁₄N₂O₁₀
• 分子量: 346.251
• InChiKey: AIYHWRFDHPMHOF-LDMBFOFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  191
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,5-dinitrophenyl β-D-mannopyranoside 在 potassium fluoride 、 Cellulomonas fimi β-mannoside (Man2A E429A) 作用下， 以 水 为溶剂， 反应 0.33h， 生成 β-D-Man-F
  参考文献：
  名称：

  碳氟键的酶促合成。

  摘要：

  DOI：

  10.1021/ja005855q

文献信息

• Engineered enzymes and their use for synthesis of thioglycosides
  申请人：Withers G Stephen

  公开号：US20060035342A1

  公开（公告）日：2006-02-16

  Mutant glycosidases in which the amino acid in the active site that serves as the acid, base or acid/base-catalyst is converted from a carboxylic acid to some other amino acid (for example to a simple alkyl, as in alanine or glycine) can catalyze the reaction of a thiosugar acceptor and an activated donor to form a thioglycoside. The “thioglycoligases” represent a novel class of mutant enzymes, and represent a first aspect of the invention. Thioglycoligases can be used in accordance with the method of the invention to couple a thiosugar acceptor and an activated donor to form a thioglycoside. By selection of the donor and acceptor species, as well as the specific enzyme employed, thioglycosides of different structure and stereochemistry can be obtained.

  突变的糖苷酶中，活性位点中作为酸、碱或酸碱催化剂的氨基酸从羧酸转变为其他氨基酸（例如转变为简单的烷基，如丙氨酸或甘氨酸），可以催化硫代糖受体和活化供体的反应，形成硫代糖苷。 "硫代糖聚合酶"代表一类新型突变酶，并代表本发明的第一个方面。可以根据本发明的方法使用硫代糖聚合酶将硫代糖受体和活化供体偶联形成硫代糖苷。通过选择供体和受体物种以及特定的酶，可以获得不同结构和立体化学的硫代糖苷。
• Engineered Enzymes and Their Use for Synthesis of Thioglycosides
  申请人：Withers G. Stephen

  公开号：US20070004010A1

  公开（公告）日：2007-01-04

  Mutant glycosidases in which the amino acid in the active site that serves as the acid, base or acid/base-catalyst is converted from a carboxylic acid to some other amino acid (for example to a simple alkyl, as in alanine or glycine) can catalyze the reaction of a thiosugar acceptor and an activated donor to form a thioglycoside. The “thioglycoligases” represent a novel class of mutant enzymes, and represent a first aspect of the invention. Thioglycoligases can be used in accordance with the method of the invention to couple a thiosugar acceptor and an activated donor to form a thioglycoside. By selection of the donor and acceptor species, as well as the specific enzyme employed, thioglycosides of different structure and stereochemistry can be obtained.

  突变的糖苷酶中，活性位点中作为酸、碱或酸碱催化剂的氨基酸从羧酸转变为其他氨基酸（例如转变为简单的烷基，如丙氨酸或甘氨酸），可以催化硫代糖受体和活化供体的反应形成硫代糖苷。这些“硫代糖合酶”代表了突变酶的一类新型酶，也代表了本发明的第一个方面。可以根据本方法使用硫代糖受体和活化供体耦合形成硫代糖苷。通过选择供体和受体物种以及具体的酶，可以获得不同结构和立体化学的硫代糖苷。
• Thioglycoligases: Mutant Glycosidases for Thioglycoside Synthesis
  作者：Michael Jahn、Jennifer Marles、R. Antony J. Warren、Stephen G. Withers

  DOI：10.1002/anie.200390114

  日期：2003.1.20
• [EN] ENGINEERED ENZYMES AND THEIR USE FOR SYNTHESIS OF THIOGLYCOSIDES<br/>[FR] ENZYMES MODIFIEES ET LEUR UTILISATION POUR LA SYNTHESE DE THIOGLYCOSIDES
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2004024908A1

  公开（公告）日：2004-03-25

  Mutant glycosidases in which the amino acid in the active site that serves as the acid, base or acid/base-catalyst is converted from a carboxylic acid to some other amino acid (for example to a simple alkyl, as in alanine or glycine) can catalyze the reaction of a thiosugar acceptor and an activated donor to form a thioglycoside. The 'thioglycoligases' represent a novel class of mutant enzymes, and represent a first aspect of the invention. Thioglycoligases can be used in accordance with the method of the invention to couple a thiosugar acceptor and an activated donor to form a thioglycoside. By selection of the donor and acceptor species, as well as the specific enzyme employed, thioglycosides of different structure and stereochemistry can be obtained.
• Enzymatic Synthesis of Carbon−Fluorine Bonds
  作者：David L. Zechel、Stephen P. Reid、Oyekanmi Nashiru、Christoph Mayer、Dominik Stoll、David L. Jakeman、R. Antony J. Warren、Stephen G. Withers

  DOI：10.1021/ja005855q

  日期：2001.5.1