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75903

Sigma-Aldrich

Guanosine

≥97.0% (HPLC)

Synonym(s):

9-(β-D-Ribofuranosyl)guanine, Guanine-9-β-D-ribofuranoside

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O5
CAS Number:
118-00-3
Molecular Weight:
283.24
Beilstein:
625911
EC Number:
204-227-8
MDL number:
MFCD00010182
UNSPSC Code:
41106305
PubChem Substance ID:
329766751
NACRES:
NA.51

Assay

≥97.0% (HPLC)

form

powder

optical activity

[α]20/D -73±2°, c = 1.5% in 1 M NaOH

impurities

≤6.0% water

mp

250 °C (dec.) (lit.)

SMILES string

[H]O[H].NC1=Nc2c(ncn2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C(=O)N1

InChI

1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1

InChI key

NYHBQMYGNKIUIF-UUOKFMHZSA-N

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Application

Guanosine is a purine nucleoside that upon sequential phosphoylation (kinases) forms GTP which is used by RNA polymerases to synthesis RNA(s). GTP is also important in a wide range of GTPase-dependent cell signaling processes. Guanosine is used in selective matricies such a guanosine gels (G-gels) for use in capillary electrophoresis chiral selection and other applications.

Other Notes

Currently available only in Europe.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Zoran D Matović et al.
Journal of inorganic biochemistry, 121, 134-144 (2013-02-05)
Novel square-planar palladium(II) complexes with O-N-N-O-type ligands H4mda (H4mda=malamido-N,N'-diacetic acid) and H4obp (H4obp=oxamido-N,N'-di-3-propionic acid) were prepared and characterized. The ligands coordinate to the palladium(II) ion via two pairs of deprotonated ligating atoms with square chelation. A four coordinate, square-planar geometry
Nadine Gehrke et al.
Immunity, 39(3), 482-495 (2013-09-03)
Immune sensing of DNA is critical for antiviral immunity but can also trigger autoimmune diseases such as lupus erythematosus (LE). Here we have provided evidence for the involvement of a damage-associated DNA modification in the detection of cytosolic DNA. The oxidized base
Michael J Osborne et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(10), 3877-3882 (2013-02-23)
Recognition of the methyl-7-guanosine (m(7)G) cap structure on mRNA is an essential feature of mRNA metabolism and thus gene expression. Eukaryotic translation initiation factor 4E (eIF4E) promotes translation, mRNA export, proliferation, and oncogenic transformation dependent on this cap-binding activity. eIF4E-cap
Jeffery T Davis et al.
Chemical Society reviews, 36(2), 296-313 (2007-02-01)
Nature's use of a simple genetic code to enable life's complex functions is an inspiration for supramolecular chemistry. DNA nucleobases carry the key information utilizing a variety of cooperative and non-covalent interactions such as hydrophobic, van der Waals, pi-pi stacking
Cynthia J Burrows et al.
Environmental health perspectives, 110 Suppl 5, 713-717 (2002-11-12)
In vitro work in this laboratory has identified new DNA lesions resulting from further oxidation of a common biomarker of oxidative damage, 8-oxo-7,8-dihydroguanine (OG). The major product of oxidation of OG in a nucleoside, nucleotide, or single-stranded oligodeoxynucleotide using metal
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