4-(β-D-ribofuranosyl)aminobenzene 5'-phosphate | 173932-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(β-D-ribofuranosyl)aminobenzene 5'-phosphate
• 英文别名: 4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate；[(2R,3S,4R,5S)-5-(4-aminophenyl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 173932-55-3
• 化学式: C₁₁H₁₆NO₇P
• 分子量: 305.224
• InChiKey: UKBUHWIOGWAJEO-DBIOUOCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  143
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  溴代丁二酸 、 4-(β-D-ribofuranosyl)aminobenzene 5'-phosphate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 4-(β-D-ribofuranosyl)-N-succinylaminobenzene 5'-phosphate
  参考文献：
  名称：

  The Conversion of a Phenol to an Aniline Occurs in the Biochemical Formation of the 1-(4-Aminophenyl)-1-deoxy-d-ribitol Moiety in Methanopterin

  摘要：

  Recent work has demonstrated that 4-hydroxybenzoic acid is the in vivo precursor to the 1-(4-aminophenyl)-1-deoxy-D-ribitol (APDR) moiety present in the C-1 carrier coenzyme methanopterin present in the methanogenic archaea. For this transformation to occur, the hydroxyl group of the 4-hydroxybenzoic acid must be replaced with an amino group at some point in the biosynthetic pathway. Using stable isotopically labeled precursors and liquid chromatography with electrospray-ionization mass spectroscopy, the first step of this transformation in Methanocaldococcus jannaschii occurs by the reaction of 4-hydroxybenzoic acid with phosphoribosyl pyrophosphate (PRPP) to form 4-(beta-D-ribofuranosyl)hydroxybenzene 5'-phosphate (beta-RAH-P). The beta-RAH-P then condenses with L-aspartate in the presence of ATP to form 4-(beta-D-ribofuranosyl)-N-succinylaminobenzene 5'-phosphate (beta-RFSA-P). Elimination of fumarate from beta-RFSA-P produces 4-(beta-D-ribofuranosyl)aminobenzene S'-phosphate (beta-RFA-P), the known precursor to the APDR moiety of methanopterin [White, R. H. (1996) Biochemistry 35, 3447-3456]. This work represents the first biochemical example of the conversion of a phenol to an aniline.

  DOI：

  10.1021/bi200362w
• 作为产物：
  描述：

  4-(β-D-ribofuranosyl)-N-succinylaminobenzene 5'-phosphate 在 Methanocaldococcus jannaschii extract 作用下， 生成 4-(α-D-ribofuranosyl)aminobenzene 5'-phosphate 、 4-(β-D-ribofuranosyl)aminobenzene 5'-phosphate
  参考文献：
  名称：

  The Conversion of a Phenol to an Aniline Occurs in the Biochemical Formation of the 1-(4-Aminophenyl)-1-deoxy-d-ribitol Moiety in Methanopterin

  摘要：

  Recent work has demonstrated that 4-hydroxybenzoic acid is the in vivo precursor to the 1-(4-aminophenyl)-1-deoxy-D-ribitol (APDR) moiety present in the C-1 carrier coenzyme methanopterin present in the methanogenic archaea. For this transformation to occur, the hydroxyl group of the 4-hydroxybenzoic acid must be replaced with an amino group at some point in the biosynthetic pathway. Using stable isotopically labeled precursors and liquid chromatography with electrospray-ionization mass spectroscopy, the first step of this transformation in Methanocaldococcus jannaschii occurs by the reaction of 4-hydroxybenzoic acid with phosphoribosyl pyrophosphate (PRPP) to form 4-(beta-D-ribofuranosyl)hydroxybenzene 5'-phosphate (beta-RAH-P). The beta-RAH-P then condenses with L-aspartate in the presence of ATP to form 4-(beta-D-ribofuranosyl)-N-succinylaminobenzene 5'-phosphate (beta-RFSA-P). Elimination of fumarate from beta-RFSA-P produces 4-(beta-D-ribofuranosyl)aminobenzene S'-phosphate (beta-RFA-P), the known precursor to the APDR moiety of methanopterin [White, R. H. (1996) Biochemistry 35, 3447-3456]. This work represents the first biochemical example of the conversion of a phenol to an aniline.

  DOI：

  10.1021/bi200362w

文献信息

• The Conversion of a Phenol to an Aniline Occurs in the Biochemical Formation of the 1-(4-Aminophenyl)-1-deoxy-<scp>d</scp>-ribitol Moiety in Methanopterin
  作者：Robert H. White

  DOI：10.1021/bi200362w

  日期：2011.7.12

  Recent work has demonstrated that 4-hydroxybenzoic acid is the in vivo precursor to the 1-(4-aminophenyl)-1-deoxy-D-ribitol (APDR) moiety present in the C-1 carrier coenzyme methanopterin present in the methanogenic archaea. For this transformation to occur, the hydroxyl group of the 4-hydroxybenzoic acid must be replaced with an amino group at some point in the biosynthetic pathway. Using stable isotopically labeled precursors and liquid chromatography with electrospray-ionization mass spectroscopy, the first step of this transformation in Methanocaldococcus jannaschii occurs by the reaction of 4-hydroxybenzoic acid with phosphoribosyl pyrophosphate (PRPP) to form 4-(beta-D-ribofuranosyl)hydroxybenzene 5'-phosphate (beta-RAH-P). The beta-RAH-P then condenses with L-aspartate in the presence of ATP to form 4-(beta-D-ribofuranosyl)-N-succinylaminobenzene 5'-phosphate (beta-RFSA-P). Elimination of fumarate from beta-RFSA-P produces 4-(beta-D-ribofuranosyl)aminobenzene S'-phosphate (beta-RFA-P), the known precursor to the APDR moiety of methanopterin [White, R. H. (1996) Biochemistry 35, 3447-3456]. This work represents the first biochemical example of the conversion of a phenol to an aniline.