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5-羥甲基胞嘧啶

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5-羥甲基胞嘧啶
Skeletal formula of 5-hydroxymethylcytosine
Ball-and-stick model of the 5-hydroxymethylcytosine molecule
IUPAC名
4-Amino-5-(hydroxymethyl)pyrimidin-2(1H)-one
識別
CAS號 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
性質
化學式 C5H7N3O2
莫耳質量 141.13 g/mol g·mol⁻¹
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

5-羥甲基胞嘧啶(5-Hydroxymethylcytosine,簡稱5hmc)是生物DNA中由胞嘧啶(C)衍生而來的一種核鹼基,其化學式為C5H7N3O2[1],可能有調控基因表現的功能,為表觀遺傳學上重要的鹼基。5hmc最早於1952年在噬菌體DNA中被發現[2][3],可能為噬菌體避免被細菌限制酶切割的一種機制,有些細菌則演化出可切割含5hmc序列的限制酶(如PvuRts1I)[4]。1972年此鹼基首度在哺乳類DNA中被發現,2009年有研究在人類與小鼠的腦組織DNA和胚胎幹細胞的DNA中發現5hmc[5][6],目前已知大多數的哺乳類細胞中可能均含有5hmc,但含量不一,在中樞神經系統神經元[7][8][9]原生殖細胞[10]中較多,且含量可能因年齡而變化[7][11]。5hmc的具體功能尚不清楚,可能與DNA去甲基化英語DNA demethylation(促進基因表現)有關[12][13]

2012年,芝加哥大學何川實驗室發表了可對基因組中5hmc進行測序的技術TAB-seq[14][15]

參考文獻

[編輯]
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