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Documenti fondamentali

G11950

Sigma-Aldrich

Guanine

98%

Sinonimo/i:

2-Amino-1,7-dihydro-6H-purin-6-one, 2-Amino-6-hydroxypurine, 2-Aminohypoxanthine

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About This Item

Formula empirica (notazione di Hill):
C5H5N5O
Numero CAS:
Peso molecolare:
151.13
Beilstein:
9680
Numero CE:
Numero MDL:
Codice UNSPSC:
12352005
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

98%

Punto di fusione

>300 °C (lit.)

Solubilità

hydrochloric acid: soluble 5 M, clear to slightly hazy, colorless to faintly yellow-green

Stringa SMILE

NC1=Nc2[nH]cnc2C(=O)N1

InChI

1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
UYTPUPDQBNUYGX-UHFFFAOYSA-N

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Descrizione generale

Adenine, cytosine, thymine and guanine are the four main nucleobases found in nucleic acids DNA and RNA. Guanine is a purine derivative. It is reported to assemble into square-planar groups that resemble macrocycles, in which the bases interact via hydrogen bonds. In DNA and RNA, stretches of guanine bases are reported to form stable four stranded helices in the presence of sodium or potassium ions. The electrochemical oxidation of guanine has been studied in aqueous media at various carbon electrodes. It reacts with peroxynitrite under physiological conditions to afford 8-nitroguanine.

Applicazioni

Guanine is suitable reagent used to investigate the mechanism of electrochemical oxidation of guanine and adenine using a glassy carbon microelectrode and cyclic and differential pulse voltammetry. It may be used in the preparation of mixed-sequence peptide nucleic acid (PNA) monomers.

Pittogrammi

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Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


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A M Oliveira-Brett et al.
Bioelectrochemistry (Amsterdam, Netherlands), 55(1-2), 61-62 (2002-01-12)
The electrochemical oxidation mechanism of guanine and adenine was investigated using a glassy carbon microelectrode and cyclic and differential pulse voltammetry. It is pH-dependent and the electron transfer process occurs in consecutive steps with the formation of strongly adsorbed dimers
K Phillips et al.
Journal of molecular biology, 273(1), 171-182 (1997-11-21)
In both DNA and RNA, stretches of guanine bases can form stable four-stranded helices in the presence of sodium or potassium ions. Sequences with a propensity to form guanine tetraplexes have been found in chromosomal telomers, immunoglobulin switch regions, and
Qian Li et al.
The journal of physical chemistry. B, 114(21), 7423-7428 (2010-05-08)
The electrochemical oxidation of guanine is studied in aqueous media at various carbon electrodes. Specifically edge plane pyrolytic graphite (EPPG), basal plane pyrolytic graphite (BPPG), and highly ordered pyrolytic graphite (HOPG) were used, and the voltammetry was found to vary
Synthesis of peptide nucleic acid monomers containing the four natural nucleobases: thymine, cytosine, adenine, and guanine and their oligomerization.
Dueholm KL, et al.
The Journal of Organic Chemistry, 59(19), 5767-5773 (1994)
V Yermilov et al.
Carcinogenesis, 16(9), 2045-2050 (1995-09-01)
Nitric oxide and superoxide anion, both formed in inflamed tissues, react rapidly to form the peroxynitrite anion (ONOO-), a strong oxidant which can initiate reactions characteristic of hydroxyl radical (HO.), nitronium ion (NO2+) and nitrogen dioxide radical (NO2.). Peroxynitrite, therefore

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