Home LiteratureArticle Details
PMID: 21862836 Published · ppublish English Journal Article Research Support, N.I.H., Extramural

Thymine DNA glycosylase can rapidly excise 5-formylcytosine and 5-carboxylcytosine: potential implications for active demethylation of CpG sites.

The Journal of biological chemistry ·Vol. 286 ·No. 41 ·2011-10-14 ·Pages 35334-35338

Maiti A, Drohat AC

Abstract

Thymine DNA glycosylase (TDG) excises T from G·T mispairs and is thought to initiate base excision repair (BER) of deaminated 5-methylcytosine (mC). Recent studies show that TDG, including its glycosylase activity, is essential for active DNA demethylation and embryonic development. These and other findings suggest that active demethylation could involve mC deamination by a deaminase, giving a G·T mispair followed by TDG-initiated BER. An alternative proposal is that demethylation could involve iterative oxidation of mC to 5-hydroxymethylcytosine (hmC) and then to 5-formylcytosine (fC) and 5-carboxylcytosine (caC), mediated by a Tet (ten eleven translocation) enzyme, with conversion of caC to C by a putative decarboxylase. Our previous studies suggest that TDG could excise fC and caC from DNA, which could provide another potential demethylation mechanism. We show here that TDG rapidly removes fC, with higher activity than for G·T mispairs, and has substantial caC excision activity, yet it cannot remove hmC. TDG excision of fC and caC, oxidation products of mC, is consistent with its strong specificity for excising bases from a CpG context. Our findings reveal a remarkable new aspect of specificity for TDG, inform its catalytic mechanism, and suggest that TDG could protect against fC-induced mutagenesis. The results also suggest a new potential mechanism for active DNA demethylation, involving TDG excision of Tet-produced fC (or caC) and subsequent BER. Such a mechanism obviates the need for a decarboxylase and is consistent with findings that TDG glycosylase activity is essential for active demethylation and embryonic development, as are mechanisms involving TDG excision of deaminated mC or hmC.

MeSH Terms
CpG Islands Cytidine/analogs & derivatives,chemistry,metabolism Cytosine/analogs & derivatives,chemistry,metabolism DNA Methylation/physiology Humans Oxidation-Reduction Substrate Specificity/physiology Thymine DNA Glycosylase/chemistry,metabolism
Chemicals
5-carboxylcytosine 5-formylcytidine Cytidine Cytosine Thymine DNA Glycosylase
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Maiti Atanu
Department of Biochemistry and Molecular Biology, University of Maryland School of Medicine, Baltimore, Maryland 21201.
Drohat Alexander C
Department of Biochemistry and Molecular Biology, University of Maryland School of Medicine, Baltimore, Maryland 21201. Electronic address: [email protected].
References (46)
46 references, click to expand
  1. Mammalian 5-formyluracil-DNA glycosylase. 2. Role of SMUG1 uracil-DNA glycosylase in repair of 5-formyluracil and other oxidized and deaminated base lesions.
    Biochemistry. 2003 May 6;42(17):5003-12 PMID: 12718543
  2. Embryonic lethal phenotype reveals a function of TDG in maintaining epigenetic stability.
    Nature. 2011 Feb 17;470(7334):419-23 PMID: 21278727
  3. The nuclear DNA base 5-hydroxymethylcytosine is present in Purkinje neurons and the brain.
    Science. 2009 May 15;324(5929):929-30 PMID: 19372393
  4. Hydroxylation of 5-methylcytosine by TET1 promotes active DNA demethylation in the adult brain.
    Cell. 2011 Apr 29;145(3):423-34 PMID: 21496894
  5. Role of Tet proteins in 5mC to 5hmC conversion, ES-cell self-renewal and inner cell mass specification.
    Nature. 2010 Aug 26;466(7310):1129-33 PMID: 20639862
  6. Definitive identification of mammalian 5-hydroxymethyluracil DNA N-glycosylase activity as SMUG1.
    J Biol Chem. 2001 Nov 9;276(45):41991-7 PMID: 11526119
  7. Cyclical DNA methylation of a transcriptionally active promoter.
    Nature. 2008 Mar 6;452(7183):45-50 PMID: 18322525
  8. DNA demethylation in hormone-induced transcriptional derepression.
    Nature. 2009 Oct 15;461(7266):1007-12 PMID: 19829383
  9. DNA demethylation in zebrafish involves the coupling of a deaminase, a glycosylase, and gadd45.
    Cell. 2008 Dec 26;135(7):1201-12 PMID: 19109892
  10. Conformation and proton configuration of pyrimidine deoxynucleoside oxidation damage products in water.
    Chem Res Toxicol. 2000 Jun;13(6):462-70 PMID: 10858319
  11. A mechanistic perspective on the chemistry of DNA repair glycosylases.
    Chem Rev. 2003 Jul;103(7):2729-59 PMID: 12848584
  12. Photochemical deamination and demethylation of 5-methylcytosine.
    Chem Res Toxicol. 1996 Jun;9(4):745-50 PMID: 8831819
  13. Formation of 5-formyl-2'-deoxycytidine from 5-methyl-2'-deoxycytidine in duplex DNA by Fenton-type reactions and gamma-irradiation.
    Nucleic Acids Res. 1999 Nov 15;27(22):4385-90 PMID: 10536146
  14. Crystal structure of human thymine DNA glycosylase bound to DNA elucidates sequence-specific mismatch recognition.
    Proc Natl Acad Sci U S A. 2008 Jul 1;105(26):8890-5 PMID: 18587051
  15. Mechanisms of base selection by human single-stranded selective monofunctional uracil-DNA glycosylase.
    J Biol Chem. 2009 Jun 5;284(23):15835-46 PMID: 19324873
  16. Coordinating the initial steps of base excision repair. Apurinic/apyrimidinic endonuclease 1 actively stimulates thymine DNA glycosylase by disrupting the product complex.
    J Biol Chem. 2008 Nov 21;283(47):32680-90 PMID: 18805789
  17. "Aromatic" substituent constants for structure-activity correlations.
    J Med Chem. 1973 Nov;16(11):1207-16 PMID: 4747963
  18. Tet-mediated formation of 5-carboxylcytosine and its excision by TDG in mammalian DNA.
    Science. 2011 Sep 2;333(6047):1303-7 PMID: 21817016
  19. The discovery of 5-formylcytosine in embryonic stem cell DNA.
    Angew Chem Int Ed Engl. 2011 Jul 25;50(31):7008-12 PMID: 21721093
  20. Oxygenase catalyzed 5-methylcytosine hydroxylation.
    Chem Biol. 2009 Jun 26;16(6):580-3 PMID: 19549596
  21. Reprogramming towards pluripotency requires AID-dependent DNA demethylation.
    Nature. 2010 Feb 25;463(7284):1042-7 PMID: 20027182
  22. CpG islands and the regulation of transcription.
    Genes Dev. 2011 May 15;25(10):1010-22 PMID: 21576262
  23. Mutagenicity of 5-formylcytosine, an oxidation product of 5-methylcytosine, in DNA in mammalian cells.
    J Biochem. 2002 Oct;132(4):551-5 PMID: 12359069
  24. Fe(II)/alpha-ketoglutarate hydroxylases involved in nucleobase, nucleoside, nucleotide, and chromatin metabolism.
    Dalton Trans. 2008 Oct 14;(38):5132-42 PMID: 18813363
  25. Enhanced CpG mutability and tumorigenesis in MBD4-deficient mice.
    Science. 2002 Jul 19;297(5580):403-5 PMID: 12130785
  26. Mismatch repair in methylated DNA. Structure and activity of the mismatch-specific thymine glycosylase domain of methyl-CpG-binding protein MBD4.
    J Biol Chem. 2003 Feb 14;278(7):5285-91 PMID: 12456671
  27. The main role of human thymine-DNA glycosylase is removal of thymine produced by deamination of 5-methylcytosine and not removal of ethenocytosine.
    J Biol Chem. 2003 Mar 7;278(10):8739-44 PMID: 12493755
  28. Role of two strictly conserved residues in nucleotide flipping and N-glycosylic bond cleavage by human thymine DNA glycosylase.
    J Biol Chem. 2009 Dec 25;284(52):36680-36688 PMID: 19880517
  29. Base analog and neighboring base effects on substrate specificity of recombinant human G:T mismatch-specific thymine DNA-glycosylase.
    Biochemistry. 1996 Oct 1;35(39):12926-32 PMID: 8841138
  30. Conversion of 5-methylcytosine to 5-hydroxymethylcytosine in mammalian DNA by MLL partner TET1.
    Science. 2009 May 15;324(5929):930-5 PMID: 19372391
  31. Thymine DNA glycosylase is essential for active DNA demethylation by linked deamination-base excision repair.
    Cell. 2011 Jul 8;146(1):67-79 PMID: 21722948
  32. Kinetics of the action of thymine DNA glycosylase.
    J Biol Chem. 1998 Aug 7;273(32):20007-14 PMID: 9685338
  33. Synthesis and properties of oligodeoxynucleotides containing 5-carboxy-2'-deoxycytidines.
    Bioorg Med Chem Lett. 2008 Jan 1;18(1):274-7 PMID: 18023346
  34. Selective chemical labeling reveals the genome-wide distribution of 5-hydroxymethylcytosine.
    Nat Biotechnol. 2011 Jan;29(1):68-72 PMID: 21151123
  35. Epigenetic reprogramming in plant and animal development.
    Science. 2010 Oct 29;330(6004):622-7 PMID: 21030646
  36. Excision of 5-halogenated uracils by human thymine DNA glycosylase. Robust activity for DNA contexts other than CpG.
    J Biol Chem. 2007 Sep 21;282(38):27578-86 PMID: 17602166
  37. Synthesis and properties of oligonucleotides containing 5-formyl-2'-deoxycytidine: in vitro DNA polymerase reactions on DNA templates containing 5-formyl-2'-deoxycytidine.
    Nucleic Acids Res. 2001 Jun 15;29(12):2456-63 PMID: 11410651
  38. The thymine glycosylase MBD4 can bind to the product of deamination at methylated CpG sites.
    Nature. 1999 Sep 16;401(6750):301-4 PMID: 10499592
  39. Activation-induced cytidine deaminase deaminates 5-methylcytosine in DNA and is expressed in pluripotent tissues: implications for epigenetic reprogramming.
    J Biol Chem. 2004 Dec 10;279(50):52353-60 PMID: 15448152
  40. Active DNA demethylation: many roads lead to Rome.
    Nat Rev Mol Cell Biol. 2010 Sep;11(9):607-20 PMID: 20683471
  41. Cloning and characterization of Rhodotorula glutinis thymine hydroxylase.
    Chem Res Toxicol. 2009 May;22(5):885-93 PMID: 19341313
  42. The Escherichia coli 3-methyladenine DNA glycosylase AlkA has a remarkably versatile active site.
    J Biol Chem. 2004 Jun 25;279(26):26876-84 PMID: 15126496
  43. Tissue distribution of 5-hydroxymethylcytosine and search for active demethylation intermediates.
    PLoS One. 2010 Dec 23;5(12):e15367 PMID: 21203455
  44. Tet proteins can convert 5-methylcytosine to 5-formylcytosine and 5-carboxylcytosine.
    Science. 2011 Sep 2;333(6047):1300-3 PMID: 21778364
  45. Stoichiometry and affinity for thymine DNA glycosylase binding to specific and nonspecific DNA.
    Nucleic Acids Res. 2011 Mar;39(6):2319-29 PMID: 21097883
  46. Specificity of human thymine DNA glycosylase depends on N-glycosidic bond stability.
    J Am Chem Soc. 2006 Sep 27;128(38):12510-9 PMID: 16984202
Article Info
Journal
The Journal of biological chemistry
Abbr.
J Biol Chem
ISSN
1083-351X
Published
2011-10-14
Epub
2011-00-23
Pages
35334-35338
Language
English
Region
United States
NLM ID
2985121R
PMCID
PMC3195571
Subset
IM
Grants
NIGMS NIH HHS · R01 GM072711 · United States
NIGMS NIH HHS · R01-GM72711 · United States
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: [email protected]