10-formyltetrahydrofolate | 2800-34-2

• 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: 10-formyltetrahydrofolate
• 英文别名: 10-formyl-THF；N-(ambo-10-formyl-5,6,7,8-tetrahydro-pteroyl)-L-glutamic acid；N-(ambo-10-Formyl-5,6,7,8-tetrahydro-pteroyl)-L-glutaminsaeure；10-formyl-(6RS)-tetrahydrofolic acid；10-formyltetrahydrofolic acid；10-Formyltetrahydropteroylglutamic acid；(2S)-2-[[4-[(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)methyl-formylamino]benzoyl]amino]pentanedioic acid
• CAS: 2800-34-2
• 化学式: C₂₀H₂₃N₇O₇
• 分子量: 473.445
• InChiKey: AUFGTPPARQZWDO-YUZLPWPTSA-N

物化性质

• 密度：
  1.68±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  216
• 氢给体数：
  7
• 氢受体数：
  10

制备方法与用途

10-甲酰基四氢叶酸是四氢叶酸的一种形式，在合成代谢中充当甲酰基的供体。它可作为甲酰转移酶反应的底物，并参与嘌呤的生物合成。

反应信息

• 作为反应物：
  描述：

  10-formyltetrahydrofolate 、 对硝基甲苯 生成 亚叶酸
  参考文献：
  名称：

  亚叶酸的合成

  摘要：

  在亚叶酸钙（5-甲酰基-5,6,7,8-四氢叶酸钙）的合成中，使用胺碱转化无水亚叶酸（5,10-甲基-5,6,7,8-四氢叶酸）酸）转化为亚叶酸意外地直接从反应混合物中产生纯（USP）产物。

  DOI：

  10.1021/ja01133a014
• 作为产物：
  描述：

  亚叶酸 在 盐酸 作用下， 以 水 为溶剂， 反应 4.5h， 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

文献信息

• [EN] METHOD AND KIT FOR ISOTOPE-LABELLING OF A FOLATE-CONTAINING BIOLOGICAL SAMPLE FOR MASS SPECTROMETRY<br/>[FR] PROCÉDÉ ET KIT DE MARQUAGE ISOTOPIQUE D'UN ÉCHANTILLON BIOLOGIQUE CONTENANT DU FOLATE POUR SPECTROMÉTRIE DE MASSE
  申请人：UNIV GRAZ MEDIZINISCHE

  公开号：WO2019161963A1

  公开（公告）日：2019-08-29

  The present invention provides a method of stabilising a biological sample comprising at least two folate species. The method comprises providing the biological sample and contacting the folate species with a reducing agent and an aliphatic aldehyde or ketone under conditions which allow reductive alkylation of at least one of the folate species, wherein the reducing agent is a deuterated reducing agent, such as formaldehyde-13C, D2, and the aliphatic aldehyde or ketone is a deuterated aliphatic aldehyde or ketone, such as cyanoborodeuteride, whereby at least one stabilised folate species isotopically labelled with D is obtained. Also provided is a biological sample containing at least one stabilised folate species selected from the group consisting of compounds I-VIII, as well as a mass-spectrometric method for quantifying folate species in the biological sample and a kit for stabilising a biological sample comprising at least two folate species for mass spectrometric analysis.

  本发明提供了一种稳定含至少两种叶酸物种的生物样品的方法。该方法包括提供生物样品并将叶酸物种与还原剂和脂肪族醛或酮接触，在允许至少一种叶酸物种还原烷基化的条件下，其中还原剂是氘代还原剂，如甲醛-13C，D2，而脂肪族醛或酮是氘代脂肪族醛或酮，如氰硼氘代物，从而获得至少一种标记有D同位素的稳定叶酸物种。还提供了一种包含从化合物I-VIII中选择的至少一种稳定叶酸物种的生物样品，以及一种用于定量生物样品中叶酸物种的质谱分析的方法和一种用于稳定含至少两种叶酸物种的生物样品进行质谱分析的试剂盒。
• Three-dimensional structure of a sugar <i>N</i> -formyltransferase from <i>Francisella tularensis</i>
  作者：Alex L. Zimmer、James B. Thoden、Hazel M. Holden

  DOI：10.1002/pro.2409

  日期：2014.3

  N‐formylated sugars have been observed on the O‐antigens of such pathogenic Gram‐negative bacteria as Campylobacter jejuni and Francisella tularensis. Until recently, however, little was known regarding the overall molecular architectures of the N‐formyltransferases that are required for the biosynthesis of these unusual sugars. Here we demonstrate that the protein encoded by the wbtj gene from F.

  在诸如空肠弯曲杆菌和土弗朗西斯菌的致病性革兰氏阴性细菌的O抗原上已观察到N甲酰化糖。然而，直到最近，对于这些异常糖的生物合成所需的N-甲酰基转移酶的整体分子结构还知之甚少。在这里，我们证明，通过对编码该蛋白质wbtj从基因土拉弗朗西斯菌是一种Ñ -formyltransferase上DTDP -4-氨基-4,6-二脱氧，其功能d -葡萄糖作为其底物。该酶在下文中称为WbtJ，显示出对N 10的严格要求甲酰基四氢叶酸为碳源。除了动力学分析外，在存在dTDP糖配体的情况下，酶的三维结构得以解析，标称分辨率为2.1Å。二聚体酶的每个亚基由Met 1至Ser 185定义的“核心”结构域控制。该核心基序带有活性位点残基。在核心结构域之后，最后56个残基折叠成两个α螺旋和一个β发夹基序。发夹基序主要负责亚基：亚基界面，其特征是相当疏水的口袋。从这里提出的研究中，现在知道WbtJ在C-4'氨基糖上起作用
• Identification of the Formycin A Biosynthetic Gene Cluster from <i>Streptomyces kaniharaensis</i> Illustrates the Interplay between Biological Pyrazolopyrimidine Formation and <i>de Novo</i> Purine Biosynthesis
  作者：Shao-An Wang、Yeonjin Ko、Jia Zeng、Yujie Geng、Daan Ren、Yasushi Ogasawara、Seema Irani、Yan Zhang、Hung-wen Liu

  DOI：10.1021/jacs.9b00241

  日期：2019.4.17

  cosmid is identified from the Streptomyces kaniharaensis genome library that contains the for gene cluster responsible for the biosynthesis of formycin. Subsequent gene deletion experiments and in vitro characterization of the forBCH gene products established their catalytic functions in formycin biosynthesis. Results also demonstrated that PurH from de novo purine biosynthesis plays a key role in pyrazolopyrimidine

  Formycin A 是一种有效的嘌呤核苷抗生素，在核糖基部分和吡唑并嘧啶碱基之间具有 C-糖苷键。在此，从卡尼哈拉链霉菌基因组文库中鉴定出粘粒，其含有负责福霉素生物合成的基因簇。随后的基因缺失实验和 forBCH 基因产物的体外表征确定了它们在福霉素生物合成中的催化功能。结果还表明，来自嘌呤从头生物合成的 PurH 在福霉素 A 生物合成过程中吡唑并嘧啶的形成中起着关键作用。PurH 在这两种途径中的参与代表了初级和次级代谢如何相互关联的一个很好的例子。
• Methods and compositions for enhancing
  申请人：——

  公开号：US06121195A1

  公开（公告）日：2000-09-19

  Methods and compositions for enhancing plant growth provide for foliar application of a substance which enhances the accumulation of formyltetrahydropteroyl polyglutamate (C.sub.1 -THF) in a treated plant. Treatment with substances that contribute to the structure of C.sub.1 -THF increase the rate and quantity of carbon fixation by the plant. Thereafter, plant growth is further improved either by exposure of the plant to elevated oxygen, illumination and heat or by foliar input of single carbon fragment sources. Optimal results are obtained by combined treatment with a substance that can serve as a sink for C.sub.1 fragments produced in the leaf.

  增强植物生长的方法和组合物，提供了一种通过叶面施用物质来增强处理植物中甲酰四氢叶酸多谷酸盐（C.sub.1-THF）积累的方法。用于增强C.sub.1-THF结构的物质处理，可以增加植物的碳固定速率和数量。之后，通过将植物暴露在高氧、光照和热等条件下或通过叶面输入单碳片段源来进一步改善植物生长。通过使用可以作为叶片中产生的C.sub.1片段的汇的物质进行联合处理，可以获得最佳效果。
• Synthetic and Degradative Investigations of the Structure of Folinic Acid-SF
  作者：Margie May、Thomas J. Bardos、Frank L. Barger、Myra Lansford、Joanne M. Ravel、George L. Sutherland、William Shive

  DOI：10.1021/ja01151a028

  日期：1951.7