5-Formylcytosine

• CAT Number: R033924
• CAS Number: 4425-59-6
• Molecular Formula: C5H5N3O2
• Molecular Weight: 139.114
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: 6-amino-2-oxo-1H-pyrimidine-5-carbaldehyde
• InChI: InChI=1S/C5H5N3O2/c6-4-3(2-9)1-7-5(10)8-4/h1-2H,(H3,6,7,8,10)
• InChIKey: FHSISDGOVSHJRW-UHFFFAOYSA-N
• SMILES: C1=NC(=O)NC(=C1C=O)N

5-Formylcytosine, also known as 5fC, is a rare base found in mammalian DNA and thought to be involved in active DNA demethylation. 5-Formylcytosine can be a stable DNA modification in mammals. 5-Formylcytosine alters the structure of the DNA double helix. 5-formylcytosine and 5-carboxylcytosine reduce the rate and substrate specificity of RNA polymerase II transcription.

Reference

1:5-Formylcytosine does not change the global structure of DNA. Hardwick JS, Ptchelkine D, El-Sagheer AH, Tear I, Singleton D, Phillips SEV, Lane AN, Brown T.Nat Struct Mol Biol. 2017 May 15. doi: 10.1038/nsmb.3411. [Epub ahead of print] PMID: 28504696 2:Single-Cell 5-Formylcytosine Landscapes of Mammalian Early Embryos and ESCs at Single-Base Resolution. Zhu C, Gao Y, Guo H, Xia B, Song J, Wu X, Zeng H, Kee K, Tang F, Yi C.Cell Stem Cell. 2017 May 4;20(5):720-731.e5. doi: 10.1016/j.stem.2017.02.013. Epub 2017 Mar 23. PMID: 28343982 3:Dealing with an Unconventional Genetic Code in  Mitochondria: The Biogenesis and Pathogenic  Defects of the 5-Formylcytosine Modification in  Mitochondrial tRNAMet. Van Haute L, Powell CA, Minczuk M.Biomolecules. 2017 Mar 2;7(1). pii: E24. doi: 10.3390/biom7010024. Review. PMID: 28257121 Free PMC Article4:Oxidized C5-methyl cytosine bases in DNA: 5-Hydroxymethylcytosine; 5-formylcytosine; and 5-carboxycytosine. Klungland A, Robertson AB.Free Radic Biol Med. 2016 Nov 24. pii: S0891-5849(16)31072-3. doi: 10.1016/j.freeradbiomed.2016.11.038. [Epub ahead of print] Review. PMID: 27890639 Free Article5:Structural Basis for Excision of 5-Formylcytosine by Thymine DNA Glycosylase. Pidugu LS, Flowers JW, Coey CT, Pozharski E, Greenberg MM, Drohat AC.Biochemistry. 2016 Nov 15;55(45):6205-6208. Epub 2016 Nov 2. PMID: 27805810 6:TET1-Mediated Oxidation of 5-Formylcytosine (5fC) to 5-Carboxycytosine (5caC) in RNA. Basanta-Sanchez M, Wang R, Liu Z, Ye X, Li M, Shi X, Agris PF, Zhou Y, Huang Y, Sheng J.Chembiochem. 2017 Jan 3;18(1):72-76. doi: 10.1002/cbic.201600328. Epub 2016 Nov 22. PMID: 27805801 7:5-Formylcytosine Could Be a Semipermanent Base in Specific Genome Sites. Su M, Kirchner A, Stazzoni S, Müller M, Wagner M, Schröder A, Carell T.Angew Chem Int Ed Engl. 2016 Sep 19;55(39):11797-800. doi: 10.1002/anie.201605994. Epub 2016 Aug 25. PMID: 27561097 8:In vivo genome-wide profiling reveals a tissue-specific role for 5-formylcytosine. Iurlaro M, McInroy GR, Burgess HE, Dean W, Raiber EA, Bachman M, Beraldi D, Balasubramanian S, Reik W.Genome Biol. 2016 Jun 29;17(1):141. doi: 10.1186/s13059-016-1001-5. PMID: 27356509 Free PMC Article9:Base pairing and structural insights into the 5-formylcytosine in RNA duplex. Wang R, Luo Z, He K, Delaney MO, Chen D, Sheng J.Nucleic Acids Res. 2016 Jun 2;44(10):4968-77. doi: 10.1093/nar/gkw235. Epub 2016 Apr 13. PMID: 27079978 Free PMC Article10:Tissue-Specific Differences in DNA Modifications (5-Hydroxymethylcytosine, 5-Formylcytosine, 5-Carboxylcytosine and 5-Hydroxymethyluracil) and Their Interrelationships. Gackowski D, Zarakowska E, Starczak M, Modrzejewska M, Olinski R.PLoS One. 2015 Dec 14;10(12):e0144859. doi: 10.1371/journal.pone.0144859. eCollection 2015. PMID: 26660343 Free PMC Article