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5-甲基胞嘧啶

5-甲基胞嘧啶
IUPAC名
4-amino-5-methyl-3H-pyrimidin-2-one
识别
CAS号 554-01-8  checkY
PubChem 65040
ChemSpider 58551
SMILES
 
  • O=C1/N=C\C(=C(\N)N1)C
InChI
 
  • 1/C5H7N3O/c1-3-2-7-5(9)8-4(3)6/h2H,1H3,(H3,6,7,8,9)
InChIKey LRSASMSXMSNRBT-UHFFFAOYAO
ChEBI 27551
KEGG C02376
MeSH 5-Methylcytosine
性质
化学式 C5H7N3O
摩尔质量 125.129 g·mol⁻¹
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

5-甲基胞嘧啶5-methylcytosine)为胞嘧啶受到甲基化之后,附加一个甲基于5号碳上的的型态,结构改变,但与互补碱基的配对性质不变。

5-甲基胞嘧啶是一种表观遗传修饰,参与的酵素称为DNA甲基转移酶(DNA methyltransferase)。对于细菌而言,5-甲基胞嘧啶可见于各式不同的位置,可用来作为一种标记,保护DNA不受自身的甲基化敏感(methylation-sensitive)限制酶破坏。在植物体内,5-甲基胞嘧啶出现于CpG与CpNpG序列里。而对真菌及动物来说,则主要存在于CpG双核苷酸(CpG dinucleotides)中。所有真核生物细胞中皆只有少量此类位置,脊椎动物的CpG胞嘧啶约有70%到80%受到甲基化。

胞嘧啶受到脱氨作用后,会转变成尿嘧啶,不过此情形相会被DNA修复酵素辨识并移除,而5-甲基胞嘧啶在脱氨作用之后则会形成胸腺嘧啶。此种转变会导致置换突变(transition mutation)的发生。

一般的胞嘧啶可在某些化学物质,如亚硝酸的作用下而发生脱氨作用,进而转变成胸腺嘧啶。5-甲基胞嘧啶可以抵抗亚硫酸所可能造成的脱氨作用,因此可用亚硫酸定序法(bisulfite sequencing)来分析DNA胞嘧啶的甲基化情形。

参考来源

  • Clark, Susan J., Janet Harrison, Cheryl L. Paul, and Marianne Frommer. (1994). High sensitivity mapping of methylated cytosines Nucleic Acids Research, Vol. 22, No. 15, 2990-2997.
  • Colot, Vincent and Jean-Luc Rossignol. (1999). Eukaryotic DNA methylation as an evolutionary device BioEssays, Vol. 21, 402-411.
  • Griffiths, Anthony J.F.; Miller, Jeffrey H.; Suzuki, David T.; Lewontin, Richard C.; & Gelbart, William M. (2000). Chapter 15: Gene Mutation in An Introduction to Genetic Analysis (7th Ed.). New York: W. H. FREEMAN. ISBN 0-7167-3520-2. (available online页面存档备份,存于互联网档案馆) at the United States National Center for Biotechnology Information)
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5-甲基胞嘧啶
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