4-amino-2-methyl-5-hydroxymethylpyrimidine phosphate | 945-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-amino-2-methyl-5-hydroxymethylpyrimidine phosphate
• 英文别名: 4-amino-5-hydroxymethyl-2-methylpyrimidine phosphate；4-amino-2-methyl-5-phosphooxymethylpyrimidine；4-Amino-2-methyl-5-hydroxymethyl-pyrimidin-phosphorsaeureester；HMP-P；Phosphorsaeure-(4-amino-2-methyl-pyrimidin-5-ylmethylester)；phosphoric acid 4-amino-2-methyl-pyrimidin-5-ylmethyl ester；(4-Amino-2-methylpyrimidin-5-YL)methyl dihydrogen phosphate
• CAS: 945-94-8
• 化学式: C₆H₁₀N₃O₄P
• 分子量: 219.137
• InChiKey: PKYFHKIYHBRTPI-UHFFFAOYSA-N

物化性质

• 熔点：
  > 176°C (dec.)
• 沸点：
  490.4±55.0 °C(Predicted)
• 密度：
  1.608±0.06 g/cm3(Predicted)
• 溶解度：
  可微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氨基-5-羟基甲基-2-甲基嘧啶 在 三氯氧磷 作用下， 生成 4-amino-2-methyl-5-hydroxymethylpyrimidine phosphate
  参考文献：
  名称：

  Competitive Inhibition of Pryidoxal Phosphate Action by Toxopyrimidine Phosphate in the Tyrosine Decarboxylase System

  摘要：

  在之前的交流中，K. Makino等人报告说，稻糠中含有“atoxopyrimidine”，可防止小鼠和大鼠因注射硫胺素嘧啶部分（2-甲基-6-氨基-5-羟甲基嘧啶，他们称之为“toxopyrimidine”）而出现抽搐或死亡。此外，他们证实维生素B6复合物具有强大的atoxopyrimidine作用1,2，表明其具有典型的“生物拮抗剂”作用，因为其结构与toxopyrimidine相似。

  DOI：

  10.1038/1741056b0

文献信息

• A “Radical Dance” in Thiamin Biosynthesis: Mechanistic Analysis of the Bacterial Hydroxymethylpyrimidine Phosphate Synthase
  作者：Abhishek Chatterjee、Amrita B. Hazra、Sameh Abdelwahed、David G. Hilmey、Tadhg P. Begley

  DOI：10.1002/anie.201003419

  日期：2010.11.8

  Tricky things with ThiC: Hydroxymethylpyrimidine phosphate (HMP‐P) synthase (ThiC) catalyzes one of the most complex rearrangement reactions in primary metabolism. Deuteration experiments show that under reducing conditions, in the presence of aminoimidazole ribonucleotide, the 5′‐deoxyadenosyl radical generated at the active site of ThiC reacts directly with the substrate and performs two iterative

  ThiC 的棘手问题：羟甲基嘧啶磷酸 (HMP-P) 合酶 (ThiC) 催化初级代谢中最复杂的重排反应之一。氘化实验表明，在还原条件下，在氨基咪唑核糖核苷酸的存在下，在 ThiC 活性位点产生的 5'-脱氧腺苷自由基直接与底物反应并进行两次迭代氢原子提取事件以催化这种重排（参见方案；SAM = S-腺苷甲硫氨酸）。
• Genetically modified bacterial cell factory for thiamine production
  申请人：BIOSYNTIA APS

  公开号：US10696992B2

  公开（公告）日：2020-06-30

  The invention provides a genetically modified bacterium for production of thiamine; where the bacterium is characterized by a transgene encoding a thiamine monophosphate phosphatase (TMP phosphatase having EC 3.1.3.-) as well as transgenes encoding polypeptides that catalyze steps in the thiamine pathway. The genetically modified bacterium is characterized by enhanced synthesis and release of thiamine into the extracellular environment. The invention further provides a method for producing thiamine using the genetically modified bacterium of the invention; as well as the use of the genetically modified bacterium for extracellular thiamine production.

  本发明提供了一种用于生产硫胺素的转基因细菌；该细菌的特征是具有编码硫胺素单磷酸磷酸酶（TMP 磷酸酶，EC 3.1.3.-）的转基因以及编码催化硫胺素途径中各步骤的多肽的转基因。转基因细菌的特点是硫胺素的合成和向胞外环境的释放得到加强。本发明进一步提供了一种利用本发明的转基因细菌生产硫胺素的方法；以及利用转基因细菌生产胞外硫胺素的方法。
• Methods of use of genes of pyridoxal 5'-phosphate biosynthesis in Bacillus subtilis: avirulent strains for vaccines, and methods for identification of antibacterial agents
  申请人：Belitsky R. Boris

  公开号：US20050287169A1

  公开（公告）日：2005-12-29

  Methods and compositions comprising a pathogenic bacterial strain having a non-reverting mutation in a pdx gene encoding an enzyme involved in pyridoxal-5′-phosphate synthesis are provided, for use in vaccines, and methods for identification of inhibitors of the enzyme for use as an antibacterial agent are provided.

  提供了包含病原细菌菌株的方法和组合物，该菌株在编码参与吡哆醛-5′-磷酸合成的酶的 pdx 基因中具有非逆转突变，可用于疫苗，还提供了鉴定用作抗菌剂的酶抑制剂的方法。
• The Thiamine Biosynthetic Enzyme ThiC Catalyzes Multiple Turnovers and Is Inhibited by S-Adenosylmethionine (AdoMet) Metabolites
  作者：Lauren D. Palmer、Diana M. Downs

  DOI：10.1074/jbc.m113.500280

  日期：2013.10

  ThiC (4-amino-5-hydroxymethyl-2-methylpyrimidine phosphate synthase; EC 4.1.99.17) is a radical S-adenosylmethionine (AdoMet) enzyme that uses a [4Fe-4S](+) cluster to reductively cleave AdoMet to methionine and a 5-deoxyadenosyl radical that initiates catalysis. In plants and bacteria, ThiC converts the purine intermediate 5-aminoimidazole ribotide to 4-amino-5-hydroxymethyl-2-methylpyrimidine phosphate, an intermediate of thiamine pyrophosphate (coenzyme B1) biosynthesis. In this study, assay conditions were implemented that consistently generated 5-fold molar excess of HMP, demonstrating that ThiC undergoes multiple turnovers. ThiC activity was improved by in situ removal of product 5-deoxyadenosine. The activity was inhibited by AdoMet metabolites S-adenosylhomocysteine, adenosine, 5-deoxyadenosine, S-methyl-5-thioadenosine, methionine, and homocysteine. Neither adenosine nor S-methyl-5-thioadenosine had been shown to inhibit radical AdoMet enzymes, suggesting that ThiC is distinct from other family members. The parameters for improved ThiC activity and turnover described here will facilitate kinetic and mechanistic analyses of ThiC.
• HMP-P KINASE AND TMP-PPASE FROM ARABIDOPSIS THALIANA AND THEIR USE IN HERBICIDE SCREENING
  申请人：Syngenta Participations AG

  公开号：EP1093520A1

  公开（公告）日：2001-04-25