4-nitrophenyl 5-deoxy-α-L-arabino-hexofuranoside | 1241819-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 5-deoxy-α-L-arabino-hexofuranoside
• 英文别名: 4-nitrophenyl 5-deoxy-β-D-galactofuranoside
• CAS: 1241819-77-1
• 化学式: C₁₂H₁₅NO₇
• 分子量: 285.254
• InChiKey: HXIRDSJJRJTIAW-NNYUYHANSA-N

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 5-deoxy-α-L-arabino-hexofuranoside 在 Penicillium fellutanum exo-β-D-galactofuranosidase 、 水 作用下， 反应 1.5h， 生成 5-deoxy-D-galactose
  参考文献：
  名称：

  Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases

  摘要：

  Derivatives of 5-deoxy-beta-D-galactofuranose (5-deoxy-alpha-L-arabino-hexofuranose) have been synthesized starting from D-galacturonic acid. The synthesis of methyl 5-deoxy-alpha-L-arabino-hexofuranoside (14 alpha) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14 alpha was converted into per-O-acetyl-5-deoxy-alpha,beta-L-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl4-promoted glycosylation of 16 led to 4-nitrophenyl (19 alpha), and 4-methylthiophenyl 5-deoxy-alpha-L-arabino-hexofuranosides (20 alpha). The oxygenated analog 4-methylphenyl 1-thio-beta-D-galactofuranoside (23 beta) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-beta-D-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.038
• 作为产物：
  描述：

  4-nitrophenyl 2,3,6-tri-O-acetyl-5-deoxy-L-arabino-hexofuranoside 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 0.5h， 生成 4-nitrophenyl 5-deoxy-α-L-arabino-hexofuranoside 、 4-nitrophenyl 5-deoxy-β-L-arabino-hexofuranoside
  参考文献：
  名称：

  Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases

  摘要：

  Derivatives of 5-deoxy-beta-D-galactofuranose (5-deoxy-alpha-L-arabino-hexofuranose) have been synthesized starting from D-galacturonic acid. The synthesis of methyl 5-deoxy-alpha-L-arabino-hexofuranoside (14 alpha) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14 alpha was converted into per-O-acetyl-5-deoxy-alpha,beta-L-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl4-promoted glycosylation of 16 led to 4-nitrophenyl (19 alpha), and 4-methylthiophenyl 5-deoxy-alpha-L-arabino-hexofuranosides (20 alpha). The oxygenated analog 4-methylphenyl 1-thio-beta-D-galactofuranoside (23 beta) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-beta-D-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.038