同: C

WordNet

a base found in DNA and RNA and derived from pyrimidine; pairs with guanine (同)C
the 3rd letter of the Roman alphabet (同)c
(music) the keynote of the scale of C major
a general-purpose programing language closely associated with the UNIX operating system
an antiviral drug used to combat HIV infection (同)ddC, DDC, zalcitabine

PrepTutorEJDIC

carbonの化学記号

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/06/03 01:33:20」(JST)

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Cytosine /ˈsaɪtɵsɨn/ (C) is one of the four main bases found in DNA and RNA, along with adenine, guanine, and thymine (uracil in RNA). It is a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attached (an amine group at position 4 and a keto group at position 2). The nucleoside of cytosine is cytidine. In Watson-Crick base pairing, it forms three hydrogen bonds with guanine.

History

Cytosine was discovered by Albrecht Kossel in 1894 when it was hydrolyzed from calf thymus tissues.^[2] A structure was proposed in 1903, and was synthesized (and thus confirmed) in the laboratory in the same year.

Cytosine recently found use in quantum computation. The first time any quantum mechanical properties were harnessed to process information took place on August 1 in 1998 when researchers at Oxford implemented David Deutsch's algorithm on a two qubit nuclear magnetic resonance quantum computer (NMRQC) based on cytosine.^[3]

Chemical reactions

Cytosine with numbered components. Methylation occurs on carbon nr 5.

Cytosine can be found as part of DNA, as part of RNA, or as a part of a nucleotide. As cytidine triphosphate (CTP), it can act as a co-factor to enzymes, and can transfer a phosphate to convert adenosine diphosphate (ADP) to adenosine triphosphate (ATP).

In DNA and RNA, cytosine is paired with guanine. However, it is inherently unstable, and can change into uracil (spontaneous deamination). This can lead to a point mutation if not repaired by the DNA repair enzymes such as uracil glycosylase, which cleaves a uracil in DNA.

Cytosine can also be methylated into 5-methylcytosine by an enzyme called DNA methyltransferase or be methylated and hydroxylated to make 5-hydroxymethylcytosine. Active enzymatic deamination of cytosine or 5-methylcytosine by the APOBEC family of cytosine deaminases could have both beneficial and detrimental implications on various cellular processes as well as on organismal evolution.^[4] The implications of deamination on 5-hydroxymethylcytosine, on the other hand, remains less understood.

References

^ Dawson, R.M.C., et al. (1959). Data for Biochemical Research. Oxford: Clarendon Press.
^ Kossel, A.; Steudel, H. Z. (1903). "Weitere Untersuchungen über das Cytosin". Physiol. Chem. 38: 49. doi:10.1515/bchm2.1903.38.1-2.49.
^ Jones, J.A.; M. Mosca (1998-08-01). "Implementation of a quantum algorithm on a nuclear magnetic resonance quantum computer". J.Chem.Phys 109 (109): 1648–1653. doi:10.1063/1.476739. Retrieved 2007-10-18.
^ Chahwan R., Wontakal S.N., and Roa S. (2010). "Crosstalk between genetic and epigenetic information through cytosine deamination". Trends in Genetics 26 (10): 443–448. doi:10.1016/j.tig.2010.07.005. PMID 20800313.

External links and Citations

Wikimedia Commons has media related to Cytosine.

Cytosine MS Spectrum

EINECS number 200-749-5
Shapiro R (1999). "Prebiotic cytosine synthesis: a critical analysis and implications for the origin of life". Proc. Natl. Acad. Sci. U.S.A. 96 (8): 4396–401. doi:10.1073/pnas.96.8.4396. PMC 16343. PMID 10200273.

UpToDate Contents

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English Journal

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Lee J1, Park J1, Hee Lee H2, Park H3, Kim HI2, Kim WJ4.
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PMID 25658488

Poly (9-(2-diallylaminoethyl)adenine HCl-co-sulfur dioxide) deposited on silica nanoparticles constructs hierarchically ordered nanocapsules: Curcumin conjugated nanocapsules as a novel strategy to amplify guanine selectivity among nucleobases.

Mouslmani M1, Bouhadir KH1, Patra D2.
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Poly (9-(2-diallylaminoethyl)adenine HCl-co-sulfur dioxide) (Poly A) deposited on silica nanoparticles self-assembles to form hierarchically ordered nanocapsules. These nanocapsules can be conjugated with curcumin. The curcumin-conjugated nanocapsules are found to be spherical in size and their size
PMID 25569875

Adenine suppresses IgE-mediated mast cell activation.

Silwal P1, Shin K1, Choi S1, Kang SW2, Park JB3, Lee HJ3, Koo SJ4, Chung KH4, Namgung U5, Lim K1, Heo JY1, Park JI1, Park SK6.
Molecular immunology.Mol Immunol.2015 Jun;65(2):242-9. doi: 10.1016/j.molimm.2015.01.021. Epub 2015 Feb 17.
Nucleobase adenine is produced by dividing human lymphoblasts mainly from polyamine synthesis and inhibits immunological functions of lymphocytes. We investigated the anti-allergic effect of adenine on IgE-mediated mast cell activation in vitro and passive cutaneous anaphylaxis (PCA) in mice. Intrap
PMID 25700347

Japanese Journal

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NAID 40020181928

DNA nanotechnology-based development of delivery systems for bioactive compounds.

Mohri Kohta,Nishikawa Makiya,Takahashi Yuki,Takakura Yoshinobu
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 58, 26-33, 2014-07-16
… In particular, we focus on the delivery of DNA containing unmethylated cytosine-phosphate-guanine (CpG) dinucleotide, or CpG motif, to immune cells expressing Toll-like receptor 9. …
NAID 120005439159

Improvement of the Antitumor Activity of Poorly Soluble Sapacitabine (CS-682) by Using Soluplus as a Surfactant

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Biological & pharmaceutical bulletin 37(5), 802-807, 2014-05
NAID 40020048858

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★リンクテーブル★

リンク元	「C」「シトシン」
拡張検索	「arabinofuranosylcytosine」「DNA-cytosine methylase」

「C」

Cytosine
	IUPAC name 4-aminopyrimidin-2(1H)-one
	Other names 4-amino-1H-pyrimidine-2-one
Identifiers
CAS number	71-30-7
PubChem	597
ChemSpider	577
UNII	8J337D1HZY
KEGG	C00380
MeSH	Cytosine
ChEBI	CHEBI:16040
ChEMBL	CHEMBL15913
Jmol-3D images	Image 1
	SMILES c1cnc(=O)[nH]c1N ;
	InChI InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8) ; Key: OPTASPLRGRRNAP-UHFFFAOYSA-N InChI=1/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8); Key: OPTASPLRGRRNAP-UHFFFAOYAY ;
Properties
Molecular formula	C4H5N3O
Molar mass	111.10 g/mol
Density	1.55 g/cm3 (calculated)
Melting point	320 to 325 °C (608 to 617 °F; 593 to 598 K) (decomposes)
Acidity (pKa)	4.45 (secondary), 12.2 (primary)
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references