(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(aziridin-1-ylmethyl)tetrahydrofuran-3,4-diol | 219497-87-7

• 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: (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(aziridin-1-ylmethyl)tetrahydrofuran-3,4-diol
• 英文别名: 5'-aziridino-5'-deoxyadenosine；N-adenosylaziridine；(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(aziridin-1-ylmethyl)oxolane-3,4-diol
• CAS: 219497-87-7
• 化学式: C₁₂H₁₆N₆O₃
• 分子量: 292.297
• InChiKey: ZUBRQACMPQRWEV-WOUKDFQISA-N

物化性质

• 熔点：
  95.5-97 °C
• 沸点：
  628.5±65.0 °C(Predicted)
• 密度：
  2.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 lithium aluminium tetrahydride 、 四丁基氟化铵 、 水 、 potassium carbonate 、 苯硫酚 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.75h， 生成 (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(aziridin-1-ylmethyl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  o-Nitrobenzenesulfonamides in Nucleoside Synthesis:  Efficient 5‘-Aziridination of Adenosine

  摘要：

  5'-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenosyl-L-methionine (SAM)-dependent methylation. We present here a highly effective synthesis of such molecules that is amenable to aziridine diversification as well as elaboration of the base moiety so as to afford "bumped" cofactor mimics compatible with "hole"-bearing mutant proteins.

  DOI：

  10.1021/jo050205w

文献信息

• 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。
• Analysis of methylation status and copy number
  申请人：Ramot at Tel-Aviv University Ltd.

  公开号：US10633706B2

  公开（公告）日：2020-04-28

  A method of diagnosing a disease associated with a DNA repeat sequence is disclosed. The method comprises: (a) determining the number of repeats of a DNA sequence in DNA molecules of a sample of the subject; and (b) determining the CpG methylation status of the DNA molecules, wherein the number of repeats of the DNA sequence and the CpG methylation status of the DNA molecules is indicative of the disease.

  本发明公开了一种与 DNA 重复序列相关的疾病诊断方法。该方法包括 (a) 确定受试者样本 DNA 分子中 DNA 序列重复序列的数目；以及 (b) 确定 DNA 分子的 CpG 甲基化状态，其中 DNA 序列的重复次数和 DNA 分子的 CpG 甲基化状态可指示疾病。
• Coupling of a Nucleoside with DNA by a Methyltransferase
  作者：Marc Pignot、Christoph Siethoff、Michael Linscheid、Elmar Weinhold

  DOI：10.1002/(sici)1521-3773(19981102)37:20<2888::aid-anie2888>3.0.co;2-4

  日期：1998.11.2

  How to outwit a methyltransferase: Methyltransferases (Mtases) catalyze the transfer of the activated methyl group from the cofactor S-adenosyl-L-methionine (1) to acceptors R within a large variety of biomolecules. Through the use of the cofactor analogue 2 a whole nucleoside was coupled to DNA in a Mtase-catalyzed reaction.
• NEW COFACTORS FOR METHYLTRANSFERASES
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP1102781B1

  公开（公告）日：2003-12-17
• New <i>S</i>-Adenosyl-<scp>l</scp>-methionine Analogues: Synthesis and Reactivity Studies
  作者：Andrew P. Townsend、Stefanie Roth、Huw E. L. Williams、Eleni Stylianou、Neil R. Thomas

  DOI：10.1021/ol9009859

  日期：2009.7.16

  Two new and complementary synthetic strategies for 5'-N-chloroethylamino-5'-deoxyadenosines are presented. Additionally, the reaction kinetics of their conversion into aziridines under typical enzyme assay conditions is reported using time-resolved NMR spectroscopy. A stable photocaged derivative of 5'-N-chloroethylamino-5'-deoxyadenosine has also been synthesized, and its stability and activation In aqueous solution at physiological pH have been examined.