S-allyl-5'-thio-adenosine | 3387-73-3

• 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-allyl-5'-thio-adenosine
• 英文别名: Allyl--sulfid；5'-Adenosyl-allylsulfid；(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(prop-2-enylsulfanylmethyl)oxolane-3,4-diol
• CAS: 3387-73-3
• 化学式: C₁₃H₁₇N₅O₃S
• 分子量: 323.376
• InChiKey: GDDLOMHXPIROTK-QYVSTXNMSA-N

物化性质

• 沸点：
  647.0±65.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-α-Boc-氨基-β-丙内酯 、 S-allyl-5'-thio-adenosine 在 甲酸 作用下， 反应 2.0h， 以29%的产率得到(allyl)(5’-deoxyadenosyl)-(N-Boc-L-cysteine)sulfonium salt
  参考文献：
  名称：

  [EN] S-ADENOSYL-L-CYSTEINE ANALOGUES AS COFACTORS FOR METHYLTRANSFERASES
  [FR] ANALOGUES DE S-ADÉNOSYL-L-CYSTÉINE UTILISÉS EN TANT QUE COFACTEURS DE MÉTHYLTRANSFÉRASES

  摘要：

  揭示了用于甲基转移酶的辅因子类似物。这些化合物由式（I）表示，其中R1为COOH或COO-；X为携带一个或多个负电荷的有机或无机阴离子；Y和Y'为H，或者是烷基；R2为NH2，NHBoc或H；Z为S或Se。R包括碳-碳双键，碳-氧双键，碳-硫双键，碳-氮双键，碳-碳三键，碳-氮三键，位于硫鎓中心的β位的芳香烃环或杂环系统，不饱和的碳-碳键，或者是碳-杂原子键，其中杂原子是O，N，S。

  公开号：

  WO2016030546A1
• 作为产物：
  描述：

  生成 S-allyl-5'-thio-adenosine
  参考文献：
  名称：

  用于选择性生物催化 Friedel-Crafts 烷基化的比较 S-腺苷-L-甲硫氨酸类似物生成

  摘要：

  甲基转移酶在生物分子的后期烷基化中具有出色的特异性。他们对S -腺苷- L -甲硫氨酸 (SAM) 的依赖要求有效地获取用于生物催化应用的 SAM 类似物。我们直接比较了卤化物甲基转移酶 (HMT) 和甲硫氨酸腺苷转移酶 (MAT) 以获得 SAM 类似物，并探索了它们在与 NovO 的级联反应中对香豆素进行区域选择性后期 Friedel-Crafts 烷基化的效用。HMT 级联有效地为甲基化提供了 SAM，而 MAT 级联也为烷基化反应提供了高水平的 SAM 类似物。

  DOI：

  10.1039/d3cc01036h

文献信息

• Facile Chemoenzymatic Strategies for the Synthesis and Utilization of<i>S</i>-Adenosyl-<scp>L</scp>-Methionine Analogues
  作者：Shanteri Singh、Jianjun Zhang、Tyler D. Huber、Manjula Sunkara、Katherine Hurley、Randal D. Goff、Guojun Wang、Wen Zhang、Chunming Liu、Jürgen Rohr、Steven G. Van Lanen、Andrew J. Morris、Jon S. Thorson

  DOI：10.1002/anie.201308272

  日期：2014.4.7

  the chemoenzymatic synthesis of 29 non‐native SAM analogues. As a proof of concept for the feasibility of natural product “alkylrandomization”, a small set of differentially‐alkylated indolocarbazole analogues was generated by using a coupled hMAT2–RebM system (RebM is the sugar C4′‐O‐methyltransferase that is involved in rebeccamycin biosynthesis). The ability to couple SAM synthesis and utilization

  据报道，用于合成S-腺苷-L-甲硫氨酸 (SAM) 类似物的化学酶平台与下游 SAM 利用酶兼容。合成了 44 种非天然 S/Se 烷基化 Met 类似物，并将其用于探测五种不同的蛋氨酸腺苷转移酶 (MAT) 的底物特异性。人类 MAT II 是所分析的 MAT 中最受允许的之一，并且能够化学酶合成 29 种非天然 SAM 类似物。作为天然产物“烷基随机化”可行性的概念证明，通过使用耦合的 hMAT2-RebM 系统（RebM 是参与瑞贝卡霉素的糖 C4'- O-甲基转移酶）生成了一小组差异烷基化吲哚并咔唑类似物。生物合成）。在单个容器中耦合 SAM 合成和利用的能力避免了与 SAM 类似物快速分解相关的问题，从而为进一步研究各种 SAM 利用酶打开了大门。
• New s-adenosyl-L-methionine analogues with extended activated groups for transfer by methyltransferases
  申请人：RWTH Aachen

  公开号：EP1712557A1

  公开（公告）日：2006-10-18

  S-Adenosyl-L-methionine analogues of formula (I) wherein wherein R comprises a carbon-carbon double bond, carbon-oxygen double bond, carbon-sulfur double bond, carbon-nitrogen double bond, a carbon-carbon triple bond, carbon-nitrogen triple bond or an aromatic carbocyclic or heterocyclic system in β-position to the sulfonium center, X- is an organic or inorganic anion carrying one or more negative charges, Z is -CR1R2-, -O-, -S- or -NR3- and R1, R2and R3 are independently selected from H, D and C1 - C12 alkyl.

  化合物公式（I）的S-腺苷基-L-甲硫氨酸类似物，其中R包括碳-碳双键，碳-氧双键，碳-硫双键，碳-氮双键，碳-碳三键，碳-氮三键或β-位于亚砜中心的芳香环烃或杂环系统，X是携带一个或多个负电荷的有机或无机阴离子，Z是-CR1R2-，-O-，-S-或-NR3-，其中R1，R2和R3独立选择自H，D和C1-C12烷基。
• Cofactor analogues for methyltransferases
  申请人：KATHOLIEKE UNIVERSITEIT LEUVEN

  公开号：US10183965B2

  公开（公告）日：2019-01-22

  Cofactor analogs for methyltransferases are disclosed. The compounds are represented by formula (I) wherein R1 is COOH or COO—; X is an organic or inorganic anion carrying one or more negative charges; Y and Y′ are H, or an alkyl; R2 is NH2, NHBoc, or H; and Z is S or Se. R comprises a carbon-carbon double bond, carbon-oxygen double bond, carbon-sulfur double bond, carbon-nitrogen double bond, a carbon-carbon triple bond, carbon-nitrogen triple bond, an aromatic carbocyclic or heterocyclic system in β-position to the sulfonium center, unsaturated c-c bond, or c-heteroatom bond where the heteroatom is O, N, S.

  本发明公开了用于甲基转移酶的辅助因子类似物。这些化合物由式（I）表示，其中 R1 是 COOH 或 COO-；X 是带有一个或多个负电荷的有机或无机阴离子；Y 和 Y′是 H 或烷基；R2 是 NH2、NHBoc 或 H；Z 是 S 或 Se。R 包括碳-碳双键、碳-氧双键、碳-硫双键、碳-氮双键、碳-碳三键、碳-氮三键、与锍中心 β 位的芳香碳环或杂环体系、不饱和 c-c 键或 c-杂原子键（其中杂原子为 O、N、S）。
• A sensitive mass spectrum assay to characterize engineered methionine adenosyltransferases with S-alkyl methionine analogues as substrates
  作者：Rui Wang、Weihong Zheng、Minkui Luo

  DOI：10.1016/j.ab.2013.12.026

  日期：2014.4

  Methionine adenosyltransferases (MATs) catalyze the formation of S-adenosyl-L-methionine (SAM) inside living cells. Recently, S-alkyl analogues of SAM have been documented as cofactor surrogates to label novel targets of methyltransferases. However, these chemically synthesized SAM analogues are not suitable for cell-based studies because of their poor membrane permeability. This issue was recently addressed under a cellular setting through a chemoenzymatic strategy to process membrane-permeable S-alkyl analogues of methionine (SAAMs) into the SAM analogues with engineered MATs. Here we describe a general sensitive activity assay for engineered MATs by converting the reaction products into S-alkylthioadenosines, followed by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) quantification. With this assay, 40 human MAT mutants were evaluated against 7 SAAMs as potential substrates. The structure-activity relationship revealed that, besides better engaged SAAM binding by the MAT mutants (lower Km value in contrast to native MATs), the gained activity toward the bulky SAAMs stems from their ability to maintain the desired linear S(N)2 transition state (reflected by higher K-cat value). Here the 11 17A mutant of human MATI was identified as the most active variant for biochemical production of SAM analogues from diverse SAAMs. (C) 2013 Elsevier Inc. All rights reserved.
• NEW S-ADENOSYL-L-METHIONINE ANALOGS WITH EXTENDED ACTIVATED GROUPS FOR TRANSFER BY METHYLTRANSFERASES
  申请人：RWTH Aachen

  公开号：EP1874790A2

  公开（公告）日：2008-01-09