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G11950

Sigma-Aldrich

Guanine

98%

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill) :
C5H5N5O
Numéro CAS:
73-40-5
Poids moléculaire :
151.13
Beilstein:
9680
Numéro CE :
200-799-8
Numéro MDL:
MFCD00071533
Code UNSPSC :
12352005
ID de substance PubChem :
24895050
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

200

Essai

98%

Pf

>300 °C (lit.)

Solubilité

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

Chaîne SMILES 

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)

Clé InChI

UYTPUPDQBNUYGX-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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.[1] The electrochemical oxidation of guanine has been studied in aqueous media at various carbon electrodes.[2] It reacts with peroxynitrite under physiological conditions to afford 8-nitroguanine.[3]

Application

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.[4] It may be used in the preparation of mixed-sequence peptide nucleic acid (PNA) monomers.[5]

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
BCCM6273
BCCM6274
BCCL0463
BCCJ0380
BCCG7899

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Purine 98%

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P55805

Purine

Hypoxanthine ≥99.0%

Sigma-Aldrich

H9377

Hypoxanthine

6-O-Methyl-d3-guanine 99 atom % D, 97% (CP)

Sigma-Aldrich

676950

6-O-Methyl-d3-guanine

2-Amino-6-chloropurine 97%

Sigma-Aldrich

342300

2-Amino-6-chloropurine

6-O-Methylguanine 97%

Sigma-Aldrich

363057

6-O-Methylguanine

Guanosine BioReagent, suitable for cell culture

Sigma-Aldrich

G6264

Guanosine

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
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
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
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
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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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