fbpx
维基百科

5-羟甲基胞嘧啶

十二月 03, 2023

5-羟甲基胞嘧啶（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，在中樞神經系統的神經元[7][8][9]及原生殖細胞[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（英语：DNA demethylation）（促進基因表現）有關[12][13]。

5-羟甲基胞嘧啶
IUPAC名
4-Amino-5-(hydroxymethyl)pyrimidin-2(1H)-one
识别
CAS号 1123-95-1  Y
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。

2012年，芝加哥大學的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 编辑

  1. ^ . nextbio.com. [2022-01-21]. （原始内容存档于2017-09-04）. 
  2. ^ Warren, RA. Modified bases in bacteriophage DNAs. Annu. Rev. Microbiol. 1980, 34: 137–158. PMID 7002022. doi:10.1146/annurev.mi.34.100180.001033. 
  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. 
  4. ^ Borgaro, JG; Zhu, Z. Characterization of the 5-hydroxymethylcytosine-specific DNA restriction endonucleases.. Nucleic Acids Research. April 2013, 41 (7): 4198–206. PMC 3627594  . PMID 23482393. doi:10.1093/nar/gkt102. 
  5. ^ Kriaucionis, S; Heintz, N. The nuclear DNA base 5-hydroxymethylcytosine is present in Purkinje neurons and the brain. Science. May 2009, 324 (5929): 929–930. Bibcode:2009Sci...324..929K. PMC 3263819  . PMID 19372393. doi:10.1126/science.1169786. 
  6. ^ Tahiliani M; et al. (PDF). Science. May 2009, 324 (5929): 930–935 [2022-01-21]. Bibcode:2009Sci...324..930T. PMC 2715015  . PMID 19372391. doi:10.1126/science.1170116. （原始内容 (PDF)存档于2022-01-21）. 
  7. ^ 7.0 7.1 Münzel M; et al. Quantification of the Sixth DNA Base Hydroxymethylcytosine in the Brain. Angew. Chem. Int. Ed. July 2010, 49 (31): 5375–5377. PMID 20583021. doi:10.1002/anie.201002033. 
  8. ^ Szwagierczak A; et al. Sensitive Enzymatic Quantification of 5-Hydroxymethylcytosine in Genomic DNA. Nucleic Acids Res. October 2010, 38 (19): e181. PMC 2965258  . PMID 20685817. doi:10.1093/nar/gkq684. 
  9. ^ Globisch D; et al. Croft, Anna Kristina , 编. Tissue Distribution of 5-Hydroxymethylcytosine and Search for Active Demethylation Intermediates. PLOS ONE. December 2010, 5 (12): e15367. Bibcode:2010PLoSO...515367G. PMC 3009720  . PMID 21203455. doi:10.1371/journal.pone.0015367  . 
  10. ^ Hackett, JA; Sengupta, R; Zylicz, JJ; Murakami, K; Lee, C; Down, T; Surani, MA. Germline DNA demethylation dynamics and imprint erasure through 5-hydroxymethylcytosine. Science. 2012-12-06, 339 (6118): 448–52. PMC 3847602  . PMID 23223451. doi:10.1126/science.1229277. 
  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  . 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  . 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  . PMID 28847947. doi:10.1073/pnas.1708044114  . 
  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  . 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  . PMID 21151123. doi:10.1038/nbt.1732. 

十二月 03, 2023
羟甲基胞嘧啶, hydroxymethylcytosine, 簡稱5hmc, 是生物dna中由胞嘧啶, 衍生而來的一種核鹼基, 其化學式為c5h7n3o2, 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, 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, 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, 目前已知大多數. 5 羟甲基胞嘧啶 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 在中樞神經系統的神經元 7 8 9 及原生殖細胞 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 英语 DNA demethylation 促進基因表現 有關 12 13 5 羟甲基胞嘧啶IUPAC名4 Amino 5 hydroxymethyl pyrimidin 2 1H one识别CAS号 1123 95 1 YPubChem 70751ChemSpider 63916SMILES C1 NC O NC C1CO NInChI 1 C5H7N3O2 c6 4 3 2 9 1 7 5 10 8 4 h1 9H 2H2 H3 6 7 8 10 InChIKey RYVNIFSIEDRLSJ UHFFFAOYATChEBI 76792性质化学式 C5H7N3O2摩尔质量 141 13 g mol g mol 若非注明 所有数据均出自标准状态 25 100 kPa 下 2012年 芝加哥大學的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 编辑 nbsp 分子与细胞生物学主题 5 Hydroxymethylcytosine nextbio com 2022 01 21 原始内容存档于2017 09 04 Warren RA Modified bases in bacteriophage DNAs Annu Rev Microbiol 1980 34 137 158 PMID 7002022 doi 10 1146 annurev mi 34 100180 001033 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 Borgaro JG Zhu Z Characterization of the 5 hydroxymethylcytosine specific DNA restriction endonucleases Nucleic Acids Research April 2013 41 7 4198 206 PMC 3627594 nbsp PMID 23482393 doi 10 1093 nar gkt102 Kriaucionis S Heintz N The nuclear DNA base 5 hydroxymethylcytosine is present in Purkinje neurons and the brain Science May 2009 324 5929 929 930 Bibcode 2009Sci 324 929K PMC 3263819 nbsp PMID 19372393 doi 10 1126 science 1169786 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 nbsp PMID 19372391 doi 10 1126 science 1170116 原始内容 PDF 存档于2022 01 21 7 0 7 1 Munzel M et al Quantification of the Sixth DNA Base Hydroxymethylcytosine in the Brain Angew Chem Int Ed July 2010 49 31 5375 5377 PMID 20583021 doi 10 1002 anie 201002033 Szwagierczak A et al Sensitive Enzymatic Quantification of 5 Hydroxymethylcytosine in Genomic DNA Nucleic Acids Res October 2010 38 19 e181 PMC 2965258 nbsp PMID 20685817 doi 10 1093 nar gkq684 Globisch D et al Croft Anna Kristina 编 Tissue Distribution of 5 Hydroxymethylcytosine and Search for Active Demethylation Intermediates PLOS ONE December 2010 5 12 e15367 Bibcode 2010PLoSO 515367G PMC 3009720 nbsp PMID 21203455 doi 10 1371 journal pone 0015367 nbsp Hackett JA Sengupta R Zylicz JJ Murakami K Lee C Down T Surani MA Germline DNA demethylation dynamics and imprint erasure through 5 hydroxymethylcytosine Science 2012 12 06 339 6118 448 52 PMC 3847602 nbsp PMID 23223451 doi 10 1126 science 1229277 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 nbsp PMID 21151123 doi 10 1038 nbt 1732 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 nbsp PMID 21496894 doi 10 1016 j cell 2011 03 022 Mellen 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 nbsp PMID 28847947 doi 10 1073 pnas 1708044114 nbsp 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 nbsp PMID 22608086 doi 10 1016 j cell 2012 04 027 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 nbsp PMID 21151123 doi 10 1038 nbt 1732 取自 https zh wikipedia org w index php title 5 羟甲基胞嘧啶 amp oldid 76860636, 维基百科，wiki，书籍，书籍，图书馆，

文章

，阅读，下载，免费，免费下载，mp3，视频，mp4，3gp， jpg，jpeg，gif，png，图片，音乐，歌曲，电影，书籍，游戏，游戏。