N¹-<(5''-Phospho-β-D-ribosyl)formimino>-5-aminoimidazole-4-carboxamide ribonucleoside

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: N¹-<(5''-Phospho-β-D-ribosyl)formimino>-5-aminoimidazole-4-carboxamide ribonucleoside
• 英文别名: N¹-[(5''-Phospho-β-D-ribosyl)formimino]-5-aminoimidazole-4-carboxamide ribonucleoside；[(2R,3S,4R,5R)-5-[(E)-[[5-carbamoyl-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazol-4-yl]amino]methylideneamino]-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• 化学式: C₁₅H₂₄N₅O₁₂P
• 分子量: 497.356
• InChiKey: MUEUOPFGMYIVFY-KEOHHSTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  272
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  5’-三磷酸腺苷 以 水 为溶剂， 反应 6.0h， 生成 N¹-<(5''-Phospho-β-D-ribosyl)formimino>-5-aminoimidazole-4-carboxamide ribonucleoside
  参考文献：
  名称：

  A plasmid-based approach for the synthesis of a histidine biosynthetic intermediate

  摘要：

  A novel plasmid DNA construct has been developed for use in the synthesis of a histidine biosynthesis intermediate,N-1-C(5''-phospho-beta-D-ribosyl)formimino]-5-aminoimidazole-4 carboxamide ribonucleotide (5'-ProFAR, 1). The approach allows for a convenient, millimole-scale preparation of the bis-ribosyl nucleotide and provides material of suitable purity for spectral analyses and biochemical studies. A highly enriched source of the first three enzymes in the histidine biosynthetic pathway has been developed by constructing a recombinant DNA plasmid which directs the overexpression of these proteins. When used in a strain of Escherichia ia coil that is devoid of other histidine biosynthetic enzymes, cell-free extracts can be coupled with 5-phospho-D-ribosyl alpha-1-pyrophosphate synthetase and an ATP recycling system to prepare 1 directly from D-ribose 5-phosphate. This paper also presents the first spectral analysis of 5'-ProFAR and its major decomposition products.

  DOI：

  10.1021/jo00080a022

文献信息

• A plasmid-based approach for the synthesis of a histidine biosynthetic intermediate
  作者：V. Jo Davisson、Ina L. Deras、Susan E. Hamilton、Landon L. Moore

  DOI：10.1021/jo00080a022

  日期：1994.1

  A novel plasmid DNA construct has been developed for use in the synthesis of a histidine biosynthesis intermediate,N-1-C(5''-phospho-beta-D-ribosyl)formimino]-5-aminoimidazole-4 carboxamide ribonucleotide (5'-ProFAR, 1). The approach allows for a convenient, millimole-scale preparation of the bis-ribosyl nucleotide and provides material of suitable purity for spectral analyses and biochemical studies. A highly enriched source of the first three enzymes in the histidine biosynthetic pathway has been developed by constructing a recombinant DNA plasmid which directs the overexpression of these proteins. When used in a strain of Escherichia ia coil that is devoid of other histidine biosynthetic enzymes, cell-free extracts can be coupled with 5-phospho-D-ribosyl alpha-1-pyrophosphate synthetase and an ATP recycling system to prepare 1 directly from D-ribose 5-phosphate. This paper also presents the first spectral analysis of 5'-ProFAR and its major decomposition products.