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Merck
CN

75903

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
UNSPSC Code:
41106305
PubChem Substance ID:
329766751
NACRES:
NA.51

Key Documents

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Quality Level

200

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

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Certificates of Analysis (COA)

Lot/Batch Number
1439351
BCBZ9127
BCBZ9122
0001439351
1439351V

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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
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
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
Jacob K Grohman et al.
Science (New York, N.Y.), 340(6129), 190-195 (2013-03-09)
RNA chaperones are ubiquitous, heterogeneous proteins essential for RNA structural biogenesis and function. We investigated the mechanism of chaperone-mediated RNA folding by following the time-resolved dimerization of the packaging domain of a retroviral RNA at nucleotide resolution. In the absence
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