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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
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
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
Zhe Li et al.
Nucleic acids research, 42(6), 4068-4079 (2013-12-29)
G-quadruplex-forming oligonucleotides containing modified nucleotide chemistries have demonstrated promising pharmaceutical potential. In this work, we systematically investigate the effects of sugar-modified guanosines on the structure and stability of a (4+0) parallel and a (3+1) hybrid G-quadruplex using over 60 modified
Thomas Gonatopoulos-Pournatzis et al.
The Biochemical journal, 457(2), 231-242 (2013-12-21)
The 7mG (7-methylguanosine cap) formed on mRNA is fundamental to eukaryotic gene expression. Protein complexes recruited to 7mG mediate key processing events throughout the lifetime of the transcript. One of the most important mediators of 7mG functions is CBC (cap-binding
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