5,10-methylidyne-5,6,7,8-tetrahydrofolic acid | 807328-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 5,10-methylidyne-5,6,7,8-tetrahydrofolic acid
• 英文别名: 5,10-Methenyltetrahydrofolate；(2S)-2-[[4-(3-amino-1-oxo-5,6,6a,7-tetrahydro-2H-imidazo[1,5-f]pteridin-10-ium-8-yl)benzoyl]amino]pentanedioic acid
• CAS: 807328-63-8
• 化学式: C₂₀H₂₂N₇O₆
• 分子量: 456.438
• InChiKey: MEANFMOQMXYMCT-ABLWVSNPSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  190
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,10-methylidyne-5,6,7,8-tetrahydrofolic acid 反应 0.5h， 生成 10-formyltetrahydrofolate
  参考文献：
  名称：

  An Enzymatic Pathway for the Biosynthesis of the Formylhydroxyornithine Required for Rhodochelin Iron Coordination

  摘要：

  Rhodochelin, a mixed catecholate-hydroxamate type siderophore isolated from Rhodococcus jostii RHA1, holds two L-delta-N-formyl-delta-N-hydroxyornithine (L-fhOrn) moieties essential for proper iron coordination. Previously, bioinformatic and genetic analysis proposed rmo and rft as the genes required for the tailoring of the L-ornithine (L-Orn) precursor [Bosello, M. (2011) J. Am. Chem. Soc. 133, 4587-4595]. In order to investigate if both Rmo and Rft constitute a pathway for L-fhOrn biosynthesis, the enzymes were heterologously produced and assayed in vitro. In the presence of molecular oxygen, NADPH and FAD, Rmo monooxygenase was able to convert L-Orn into L-delta-N-hydroxyornithine (L-hOrn). As confirmed in a coupled reaction assay, this hydroxylated intermediate serves as a substrate for the subsequent N-10-formyl-tetrahydrofolate-dependent (N-10-fH(4)F) Rtf-catalyzed formylation reaction, establishing a route for the L-fhOrn biosynthesis, prior to its incorporation by the NAPS assembly line. It is of particular interest that a major improvement to this study has been reached with the use of an alternative approach to the chemoenzymatic FolD-dependent N-10-fH(4)F conversion, also rescuing the previously inactive CchA, the Rft-homologue in coelichelin assembly line [Buchenau, B. (2004) Arch. Microbiol. 182, 313-325; Pohlmann, V. (2008) Org. Biomol. Chem. 6, 1843-1848].

  DOI：

  10.1021/bi201837f
• 作为产物：
  描述：

  亚叶酸 在 1,4-双(2-羟基乙基)哌嗪 、 5,10-methenyltetrahydrofolate synthetase 、 MgATP 、 2-巯基乙醇 作用下， 生成 5,10-methylidyne-5,6,7,8-tetrahydrofolic acid
  参考文献：
  名称：

  鸡肝中5,10-甲基四氢叶酸合成酶的纯化与鉴定

  摘要：

  다있었。다。ATP，Kg，MgATP，MgCTP，MgUTP和MgGTP，以及MgATP和其他产品。用四硝基met烷（1-硝基-3-（3-二甲基氨基丙基）-碳二亚胺），酪氨酸和羧酸盐进行脱硫。产品名称：5,10-甲基四氢叶酸合成酶，간，대사，테트라니트로메탄，1-乙基-3-（3-二甲基氨基丙基）-碳二亚胺摘要。通过30-70％硫酸铵分级分离，Q Sepharose Fast Flow阴离子交换和Source 15Phe疏水作用色谱法纯化来自鸡肝的5,10-甲基四氢叶酸合成酶。细胞提取物，硫酸铵，Q Sepharose Fast Flow和Source 15Phe的比活分别为0.0085、0.031、0.80和1.27 U / mg。细胞提取物，硫酸铵，Q Sepharose Fast Flow和Source 15Phe的纯化折叠活性分别为1，分别为3.7、94.1和149.4。HPLC凝胶

  DOI：

  10.5012/jkcs.2010.54.5.567

文献信息

• Synthesis of leucovorin
  申请人：Burroughs Wellcome Co.

  公开号：US04500711A1

  公开（公告）日：1985-02-19

  In the synthesis of calcium leucovorin (calcium 5-formyl-5,6,7,8-tetrahydrofolate), the use of an amine base in the conversion of anhydroleucovorin (5,10-methenyl-5,6,7,8-tetrahydrofolic acid) to leucovorin unexpectedly results in a pure (USP) product directly from the reaction mixture.

  在合成钙亚叶酸钙（钙5-甲酰基-5,6,7,8-四氢叶酸）时，使用胺基在将无水亚叶酸（5,10-亚甲基-5,6,7,8-四氢叶酸）转化为亚叶酸的过程中，意外地直接从反应混合物中得到纯（USP）产物。
• Charlton, Peter A.; Young, Douglas W.; Birdsall, Berry, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1349 - 1354
  作者：Charlton, Peter A.、Young, Douglas W.、Birdsall, Berry、Feeney, James、Roberts, Gordon C. K.

  DOI：——

  日期：——
• An Enzymatic Pathway for the Biosynthesis of the Formylhydroxyornithine Required for Rhodochelin Iron Coordination
  作者：Mattia Bosello、Andreas Mielcarek、Tobias W. Giessen、Mohamed A. Marahiel

  DOI：10.1021/bi201837f

  日期：2012.4.10

  Rhodochelin, a mixed catecholate-hydroxamate type siderophore isolated from Rhodococcus jostii RHA1, holds two L-delta-N-formyl-delta-N-hydroxyornithine (L-fhOrn) moieties essential for proper iron coordination. Previously, bioinformatic and genetic analysis proposed rmo and rft as the genes required for the tailoring of the L-ornithine (L-Orn) precursor [Bosello, M. (2011) J. Am. Chem. Soc. 133, 4587-4595]. In order to investigate if both Rmo and Rft constitute a pathway for L-fhOrn biosynthesis, the enzymes were heterologously produced and assayed in vitro. In the presence of molecular oxygen, NADPH and FAD, Rmo monooxygenase was able to convert L-Orn into L-delta-N-hydroxyornithine (L-hOrn). As confirmed in a coupled reaction assay, this hydroxylated intermediate serves as a substrate for the subsequent N-10-formyl-tetrahydrofolate-dependent (N-10-fH(4)F) Rtf-catalyzed formylation reaction, establishing a route for the L-fhOrn biosynthesis, prior to its incorporation by the NAPS assembly line. It is of particular interest that a major improvement to this study has been reached with the use of an alternative approach to the chemoenzymatic FolD-dependent N-10-fH(4)F conversion, also rescuing the previously inactive CchA, the Rft-homologue in coelichelin assembly line [Buchenau, B. (2004) Arch. Microbiol. 182, 313-325; Pohlmann, V. (2008) Org. Biomol. Chem. 6, 1843-1848].
• Purification and Characterization of 5,10-Methenyltetrahydrofolate Synthetase from Chicken Liver
  作者：Yong-Kweon Cho

  DOI：10.5012/jkcs.2010.54.5.567

  日期：2010.10.20

  테트라니트로메탄, 1-Ethyl-3-(3-dimethyl aminopropyl)- carbodiimide ABSTRACT. 5,10-Methenyltetrahydrofolate synthetase from chicken liver was purified through 30-70% ammonium sulfate fractionation, Q Sepharose Fast Flow anion exchange and Source 15Phe hydrophobic interaction chromatography. Specific activities of cell extract, ammonium sulfate, Q Sepharose Fast Flow and Source 15Phe were 0.0085, 0.031, 0.80 and

  다있었。다。ATP，Kg，MgATP，MgCTP，MgUTP和MgGTP，以及MgATP和其他产品。用四硝基met烷（1-硝基-3-（3-二甲基氨基丙基）-碳二亚胺），酪氨酸和羧酸盐进行脱硫。产品名称：5,10-甲基四氢叶酸合成酶，간，대사，테트라니트로메탄，1-乙基-3-（3-二甲基氨基丙基）-碳二亚胺摘要。通过30-70％硫酸铵分级分离，Q Sepharose Fast Flow阴离子交换和Source 15Phe疏水作用色谱法纯化来自鸡肝的5,10-甲基四氢叶酸合成酶。细胞提取物，硫酸铵，Q Sepharose Fast Flow和Source 15Phe的比活分别为0.0085、0.031、0.80和1.27 U / mg。细胞提取物，硫酸铵，Q Sepharose Fast Flow和Source 15Phe的纯化折叠活性分别为1，分别为3.7、94.1和149.4。HPLC凝胶