S-adenosyl-L-[Me-(14)C]methionine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: S-adenosyl-L-[Me-(14)C]methionine
• 英文别名: [Me-14C]-S-adenosyl-L-methionine；S-adenosyl-L-[methyl-(14)C]methionine；[¹⁴C]-S-adenosyl-L-methionine；[methyl-¹⁴C]S-adenosylmethionine；[(14)C-methyl]-S-adenosyl-L-methionine；S-[methyl-14C] adenosyl-L-methionine；[methyl-(14)C]AdoMet；14C-methyl-SAM；AdoMet；[methyl-14C]-S-adenosyl-L-methionine；[(14)C-methyl]-S-adenosyl-L-Met；[(14)C]AdoMet；Adenosine,5'-[[(3S)-3-amino-3-carboxypropyl]methyl-14c-sulfonio]-5'-deoxy-,inner salt(9ci)；(2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-(114C)methylsulfonio]butanoate
• 化学式: C₁₅H₂₂N₆O₅S
• 分子量: 400.432
• InChiKey: MEFKEPWMEQBLKI-JMJUVHIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  187
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  S-adenosyl-L-[Me-(14)C]methionine 在 SAM decarboxylase 作用下， 以 aq. buffer 为溶剂， 反应 0.25h， 生成 3-aminopropyl-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-(114C)methylsulfanium
  参考文献：
  名称：

  通过非常规自由基 S-腺苷甲硫氨酸酶在二苯甲胺生物合成中进行底物依赖性切割位点选择

  摘要：

  S-腺苷甲硫氨酸 (SAM) 的锍离子具有三个不同的 CS 键。传统的自由基SAM酶使用[4Fe-4S]簇来均裂SAM的C5'、腺苷-S键，生成5'-脱氧腺苷自由基，催化各种下游化学反应。参与二苯甲酰胺生物合成的自由基 SAM 酶，例如 Pyrococcus horikoshii Dph2 (PhDph2) 和酵母 Dph1-Dph2，而是裂解甲硫氨酸的 Cγ,Met-S 键以生成 3-氨基-3-羧丙基自由基。我们在这里展示了自由基 SAM 酶可以通过改变 SAM 的结构来调整以切割与锍硫的第三个 CS 键。使用脱羧基 SAM 类似物 (dc-SAM)，PhDph2 裂解 C 甲基-S 键，形成 5'-脱氧-5'-(3-氨基丙硫基) 腺苷 (dAPTA, 1)。甲基裂解活性，像其他两个 CS 键的断裂一样，取决于 [4Fe-4S]+ 簇的存在。电子-核双共振和质谱数据表明 [4Fe-4S]

  DOI：

  10.1021/jacs.7b01712

文献信息

• <i>N</i>^η-Substituted Arginyl Peptide Inhibitors of Protein Arginine <i>N</i>-Methyltransferases
  作者：Ted M. Lakowski、Peter ’t Hart、Christopher A. Ahern、Nathaniel I. Martin、Adam Frankel

  DOI：10.1021/cb100161u

  日期：2010.11.19

  methylation site via mass spectrometry. Although weak inhibitors of CARM1, R1-1, -2, -3, and -4 are potent inhibitors of PRMT1 and PRMT6. These peptides are more potent against PRMT1 than product inhibitor peptides, showing that Nη-substituted arginyl peptides do not work by a purely product inhibitor mechanism. A trend of increasing potency with an increase in the number of fluorine atoms is observed

  蛋白质精氨酸N-甲基转移酶（PRMT）催化底物蛋白质内精氨酸残基的翻译后甲基化。它们在基因表达的表观遗传调控中的作用使它们成为药物发现的可行靶标。合成了含有一个单个精氨酸残基的肽，该肽在胍基氮（Nη）上被一个带有零至三个氟原子的乙基（R1-1，-2，-3和-4）取代，并测试了其甲基化和抑制活性与PRMT1，PRMT6和CARM1。只有非氟化R1-1肽通过PRMT1甲基化，这表明Ñ η取代精氨酸被其活性位点容纳。R1-1乙基取代的胍Nη通过质谱进一步确定“甲基化”为甲基化位点。尽管CARM1，R1-1，-2，-3和-4的弱抑制剂是PRMT1和PRMT6的有效抑制剂。这些肽是针对PRMT1比产物抑制剂的肽更有效，表明Ñ η取代精氨酰肽由纯产物抑制剂机构不工作。对于PRMT1，观察到随着氟原子数目的增加，效力增加的趋势，这可能是由于胍基偶极矩的相应变化所致。R1-1肽的乙基精氨酸部分的模型表明，
• S-adenosyl-l-methionine: Anol-O-methyltransferase activity in organ cultures of Pimpinella anisum
  作者：Birgitt Kemmerer、Jürgen Reichling

  DOI：10.1016/0031-9422(95)00880-2

  日期：1996.5

  Abstract The biosynthesis of epoxypseudoisoeugenol-2-methylbutyrate (EPB), a rare phenylpropanoid of the genus Pimpinella , was investigated in vitro by means of a leaf-differentiating callus culture of Pimpinella anisum . In an effort to corroborate an earlier proposed biosynthetic pathway of EPB, the step between p -coumaryl alcohol and ( E )-anethole was reinvestigated. Further feeding experiments

  摘要 通过茴香叶片分化愈伤组织培养，体外研究了一种稀有的茴香属苯丙烷环氧假异丁香酚-2-甲基丁酸酯（EPB）的生物合成。为了证实早先提出的 EPB 生物合成途径，重新研究了对香豆醇和 (E)-茴香脑之间的步骤。用 14 C 标记的前体进行的进一步喂食实验和酶水平的初步研究清楚地表明，乙醇是 EPB 生物合成中必需的中间体，而不是之前声称的对甲氧基肉桂醇。S-腺苷-l-甲硫氨酸：醇-O-甲基转移酶是EPB生物合成中的关键酶，首次被证明和表征。
• [EN] POLYPEPTIDES FOR USE IN THE SYNTHESIS OF BIOACTIVE PHENOLIC COMPOUNDS<br/>[FR] POLYPEPTIDES DESTINÉS À ÊTRE UTILISÉS DANS LA SYNTHÈSE DE COMPOSÉS PHÉNOLIQUES BIOACTIFS
  申请人：ROTHSTEIN STEVEN

  公开号：WO2022109736A1

  公开（公告）日：2022-06-02

  Described herein is a polypeptide encoding a prenyltransferase for prenylating a polyphenol and a polypeptide encoding an O-methyltransferase for methylating a polyphenol. For example, the polypeptide comprises or consists of the sequence of SEQ ID NO: 1, 2, 3, 4, 5, and/or 6, and/or a polypeptide listed in Table 1, and/or SEQ ID NO: 7-30, or a variant thereof having at least 80% sequence identity to SEQ ID NO: 1, 2, 3, 4, 5, and/or 6, and/or the polypeptide listed in Table 1, and/or SEQ ID NO: 7-30, or a fragment of the polypeptide or the variant thereof.

  本文描述了编码一种用于对多酚进行异戊二烯基化的异戊二烯基转移酶的多肽和编码一种用于对多酚进行甲基化的O-甲基转移酶的多肽。例如，该多肽包括或仅由SEQ ID NO：1、2、3、4、5和/或6的序列组成，和/或表1中列出的多肽，和/或SEQ ID NO：7-30，或具有与SEQ ID NO：1、2、3、4、5和/或6和/或表1中列出的多肽和/或SEQ ID NO：7-30至少80％序列同一性的变异体，或该多肽或其变异体的片段。
• Protein Arginine N-Methyltransferase Substrate Preferences for Different Nη-Substituted Arginyl Peptides
  作者：Dylan Thomas、Timo Koopmans、Ted M. Lakowski、Helmi Kreinin、Mynol I. Vhuiyan、Shona A. Sedlock、Jennifer M. Bui、Nathaniel I. Martin、Adam Frankel

  DOI：10.1002/cbic.201402045

  日期：2014.7.21

  A little goes a long way: Various heteroatom substituents at the guanidine moiety of an arginine residue in an established substrate peptide can alter the protein arginine N‐methyltransferase (PRMT) activity toward it. Depending on the electrostatic nature of the substituent incorporated, PRMT activity toward the substrate peptide can be diminished, abolished, or, surprisingly, enhanced.

  有一点很长的路要走：已建立的底物肽中精氨酸残基的胍基部分的各种杂原子取代基可以改变蛋白质对其的精氨酸N-甲基转移酶（PRMT）活性。取决于引入的取代基的静电性质，对底物肽的PRMT活性可以降低，消除或令人惊讶地增强。
• Formation of UV-honey guides in Rudbeckia hirta
  作者：Karin Schlangen、Silvija Miosic、Ana Castro、Karin Freudmann、Maria Luczkiewicz、Florian Vitzthum、Wilfried Schwab、Sonja Gamsjäger、Maurizio Musso、Heidi Halbwirth

  DOI：10.1016/j.phytochem.2009.04.017

  日期：2009.5

  The UV-honey guides of Rudbeckia hirta were investigated by UV-photography, reflectance spectroscopy, LC-MS analysis and studies of the enzymes involved in the formation of the W-absorbing flavonols present in the petals. It was shown for the first time that the typical bull's eye pattern is already established at the early stages of flower anthesis on the front side of the petal surface, but is hidden to pollinators until the buds are open and the petals are unfolded. The rear side of the petals remains W-reflecting during the whole flower anthesis. Studies on the local distribution of 19 flavonols across the petals confirmed that the majority are concentrated in the basal part of the ray flower. However, in contrast to the earlier studies, eupatolitin 3-O-glucoside (6,7-dimethoxyquercetin 3-O-glucoside) was present in both the basal and apical parts of the petals, whereas eupatolin (6,7-dimethoxyquercetin 3-O-rhamnoside) was exclusively found in the apical parts. The enzymes involved in the formation of the flavonols in R. hirta were demonstrated for the first time. These include a rare flavonol 6-hydroxylase, which was identified as cytochrome P450-dependent monooxygenase and did not accept any methylated flavonol as substrate. All enzymes were present in the basal and apical parts of the petals, although some of them clearly showed higher activities in the basal part. This indicates that the local accumulation of flavonols in R. hirta is not achieved by a locally restricted presence of the enzymes involved in flavonol formation. (C) 2009 Elsevier Ltd. All rights reserved.