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5-羟甲基胞嘧啶

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5-羟甲基胞嘧啶
Skeletal formula of 5-hydroxymethylcytosine
Ball-and-stick model of the 5-hydroxymethylcytosine molecule
IUPAC名
4-Amino-5-(hydroxymethyl)pyrimidin-2(1H)-one
识别
CAS号 1123-95-1  checkY
PubChem 70751
ChemSpider 63916
SMILES
 
  • C1=NC(=O)NC(=C1CO)N
InChI
 
  • 1/C5H7N3O2/c6-4-3(2-9)1-7-5(10)8-4/h1,9H,2H2,(H3,6,7,8,10)
InChIKey RYVNIFSIEDRLSJ-UHFFFAOYAT
ChEBI 76792
性质
化学式 C5H7N3O2
摩尔质量 141.13 g/mol g·mol⁻¹
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

5-羟甲基胞嘧啶(5-Hydroxymethylcytosine,简称5hmc)是生物DNA中由胞嘧啶(C)衍生而来的一种核碱基,其化学式为C5H7N3O2[1],可能有调控基因表现的功能,为表观遗传学上重要的碱基。5hmc最早于1952年在噬菌体DNA中被发现[2][3],可能为噬菌体避免被细菌限制酶切割的一种机制,有些细菌则演化出可切割含5hmc序列的限制酶(如PvuRts1I)[4]。1972年此碱基首度在哺乳类DNA中被发现,2009年有研究在人类与小鼠的脑组织DNA和胚胎干细胞的DNA中发现5hmc[5][6],目前已知大多数的哺乳类细胞中可能均含有5hmc,但含量不一,在中枢神经系统神经元[7][8][9]原生殖细胞[10]中较多,且含量可能因年龄而变化[7][11]。5hmc的具体功能尚不清楚,可能与DNA去甲基化英语DNA demethylation(促进基因表现)有关[12][13]

2012年,芝加哥大学何川实验室发表了可对基因组中5hmc进行测序的技术TAB-seq[14][15]

参考文献

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