methyl 2,3-di-O-benzyl-β-L-altrofuranoside | 16895-91-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-β-L-altrofuranoside
• 英文别名: 2,3-di-O-benzyl-β-L-methylaltrofuranose；Methyl-2,3-di-O-benzyl-β-D-galactofuranosid；(1S)-1-[(2S,3S,4R,5R)-5-methoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]ethane-1,2-diol
• CAS: 16895-91-3；16895-96-8；16895-97-9；20869-17-4；20869-18-5；21090-87-9
• 化学式: C₂₁H₂₆O₆
• 分子量: 374.434
• InChiKey: IEUQWJFYEPQBON-ALGQRKQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-β-L-altrofuranoside 在 吡啶 、 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 硫酸 、 10% Pd(OH)2/C 、 氢溴酸 、 氢气 、 二正丁基氧化锡 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.41h， 生成 dibenzyl 2,3,6-tri-O-benzoyl-5-deoxy-5-fluoro-α-D-galactofuranose monophosphate
  参考文献：
  名称：

  Fluorosugar Chain Termination Agents as Probes of the Sequence Specificity of a Carbohydrate Polymerase

  摘要：

  Naturally occurring carbohydrate polymers are ubiquitous. They are assembled by polymerizing glycosyltransferases, which can generate polysaccharide products with repeating sequence patterns. The fidelity of enzymes of this class is unknown. We report a method for testing the fidelity of carbohydrate polymerase pattern deposition: we synthesized fluorosugar donors and used them as chain termination agents. The requisite nucleotide fluorosugars could be produced from a single intermediate using the Jacobsen catalyst in a kinetically controlled separation of diastereomers. The resulting fluorosugar donors were used by the galactofuranosyltransferase GlfT2 from Mycobacterium tuberculosis, and the data indicate that this enzyme mediates the cell wall galactan production through a sequence-specific polymerization.

  DOI：

  10.1021/ja301723p
• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 在 咪唑 、 甲醇 、 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 、 正丁基锂 、 camphor-10-sulfonic acid 、 水 、 碘 、 sodium hydride 、 溶剂黄146 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 methyl 2,3-di-O-benzyl-β-L-altrofuranoside
  参考文献：
  名称：

  Fluorosugar Chain Termination Agents as Probes of the Sequence Specificity of a Carbohydrate Polymerase

  摘要：

  Naturally occurring carbohydrate polymers are ubiquitous. They are assembled by polymerizing glycosyltransferases, which can generate polysaccharide products with repeating sequence patterns. The fidelity of enzymes of this class is unknown. We report a method for testing the fidelity of carbohydrate polymerase pattern deposition: we synthesized fluorosugar donors and used them as chain termination agents. The requisite nucleotide fluorosugars could be produced from a single intermediate using the Jacobsen catalyst in a kinetically controlled separation of diastereomers. The resulting fluorosugar donors were used by the galactofuranosyltransferase GlfT2 from Mycobacterium tuberculosis, and the data indicate that this enzyme mediates the cell wall galactan production through a sequence-specific polymerization.

  DOI：

  10.1021/ja301723p

文献信息

• Fluorosugar Chain Termination Agents as Probes of the Sequence Specificity of a Carbohydrate Polymerase
  作者：Christopher D. Brown、Max S. Rusek、Laura L. Kiessling

  DOI：10.1021/ja301723p

  日期：2012.4.18

  Naturally occurring carbohydrate polymers are ubiquitous. They are assembled by polymerizing glycosyltransferases, which can generate polysaccharide products with repeating sequence patterns. The fidelity of enzymes of this class is unknown. We report a method for testing the fidelity of carbohydrate polymerase pattern deposition: we synthesized fluorosugar donors and used them as chain termination agents. The requisite nucleotide fluorosugars could be produced from a single intermediate using the Jacobsen catalyst in a kinetically controlled separation of diastereomers. The resulting fluorosugar donors were used by the galactofuranosyltransferase GlfT2 from Mycobacterium tuberculosis, and the data indicate that this enzyme mediates the cell wall galactan production through a sequence-specific polymerization.