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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，在中枢神经系统的神经元[7][8][9]及原生殖细胞[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，芝加哥大学的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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  3. ^ Wyatt, GR; Cohen, SS. A new pyrimidine base from bacteriophage nucleic acids. Nature. December 1952, 170 (4338): 1072–1073. Bibcode:1952Natur.170.1072W. PMID 13013321. S2CID 4277592. doi:10.1038/1701072a0. 
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  6. ^ Tahiliani M; et al. Conversion of 5-methylcytosine to 5-hydroxymethylcytosine in mammalian DNA by MLL partner TET1 (PDF). Science. May 2009, 324 (5929): 930–935 [2022-01-21]. Bibcode:2009Sci...324..930T. PMC 2715015 可免费查阅. PMID 19372391. doi:10.1126/science.1170116. （原始内容 (PDF)存档于2022-01-21）. 
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  8. ^ Szwagierczak A; et al. Sensitive Enzymatic Quantification of 5-Hydroxymethylcytosine in Genomic DNA. Nucleic Acids Res. October 2010, 38 (19): e181. PMC 2965258 可免费查阅. PMID 20685817. doi:10.1093/nar/gkq684. 
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  11. ^ Song C-X; et al. Selective chemical labeling reveals the genome-wide distribution of 5-hydroxymethylcytosine. Nat. Biotechnol. December 2010, 29 (1): 68–72. PMC 3107705 可免费查阅. PMID 21151123. doi:10.1038/nbt.1732. 
  12. ^ Guo, Junjie U.; Su, Yijing; Zhong, Chun; Ming, Guo-li; Song, Hongjun. Hydroxylation of 5-Methylcytosine by TET1 Promotes Active DNA Demethylation in the Adult Brain. Cell. 1 April 2011, 145 (3): 423–434. PMC 3088758 可免费查阅. PMID 21496894. doi:10.1016/j.cell.2011.03.022. 
  13. ^ Mellén, M; Ayata, P; Heintz, N. 5-hydroxymethylcytosine accumulation in postmitotic neurons results in functional demethylation of expressed genes. Proc Natl Acad Sci U S A. Sep 2017, 114 (37): E7812–E7821. PMC 5604027 可免费查阅. PMID 28847947. doi:10.1073/pnas.1708044114 可免费查阅. 
  14. ^ Yu M, Hon GC, Szulwach KE, Song CX, Zhang L, Kim A, Li XK, Dai Q, Shen Y, Park B, Min JH, Jin P, Ren B, He C. Base-resolution analysis of 5-hydroxymethylcytosine in the mammalian genome.. Cell. June 2012, 149 (6): 1368–1380. PMC 3589129 可免费查阅. PMID 22608086. doi:10.1016/j.cell.2012.04.027. 
  15. ^ Song CX, Szulwach KE, Fu Y, Dai Q, Yi C, Li X, Li Y, Chen CH, Zhang W, Jian X, Wang J, Zhang L, Looney TJ, Zhang B, Godley LA, Hicks LM, Lahn BT, Jin P, He C. Selective chemical labeling reveals the genome-wide distribution of 5-hydroxymethylcytosine. Nat. Biotechnol. 2011, 29 (1): 68–72. PMC 3107705 可免费查阅. PMID 21151123. doi:10.1038/nbt.1732. 
取自“https://zh.wikipedia.org/w/index.php?title=5-羟甲基胞嘧啶&oldid=76860636”