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850926

Sigma-Aldrich

2′,3′,5′-Tri-O-acetylguanosine

98%

Synonym(s):

Guanosine 2′,3′,5′-triacetate

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About This Item

Empirical Formula (Hill Notation):
C16H19N5O8
CAS Number:
6979-94-8
Molecular Weight:
409.35
EC Number:
230-242-4
MDL number:
MFCD00057054
UNSPSC Code:
12352123
PubChem Substance ID:
24888303
NACRES:
NA.22

assay

98%

form

powder

mp

226-231 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(=O)OC[C@H]1O[C@H]([C@H](OC(C)=O)[C@@H]1OC(C)=O)n2cnc3C(=O)NC(N)=Nc23

InChI

1S/C16H19N5O8/c1-6(22)26-4-9-11(27-7(2)23)12(28-8(3)24)15(29-9)21-5-18-10-13(21)19-16(17)20-14(10)25/h5,9,11-12,15H,4H2,1-3H3,(H3,17,19,20,25)/t9-,11-,12-,15-/m1/s1

InChI key

ULXDFYDZZFYGIY-SDBHATRESA-N

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR6059
MKBT2645V
MKBL4290
13619LN
11708JB

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J C Niles et al.
Journal of the American Chemical Society, 123(49), 12147-12151 (2001-12-06)
Peroxynitrite reacts with 2',3',5'-tri-O-acetyl-guanosine to yield a novel compound identified as 1-(2,3,5-tri-O-acetyl-beta-D-erythro-pentofuranosyl)-5-guanidino-4-nitroimidazole (6). This characterization was achieved using a combination of UV/vis spectroscopy and ESI-MS. Additionally, 1-(beta-D-erythro-pentofuranosyl)-5-guanidino-4-nitroimidazole (6a) was synthesized by an independent route, characterized by UV/vis spectroscopy, ESI-MS, and
K H Leser
Zeitschrift fur Naturforschung. Section C, Biosciences, 36(7-8), 597-603 (1981-07-01)
Various drugs known or expected to increase the levels of cyclic nucleotides in cells were applied to isolated superfused frog retinae, and their influence on the aspartate-isolated a-wave was studied. Isobutylmethylxanthine (IBMX), triacetylguanosine (TAG), and dimethylaminopurine (DAMP) strongly influenced the
G A Freeman et al.
Bioorganic & medicinal chemistry, 3(4), 447-458 (1995-04-01)
A series of 2-amino-9-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)-6- substituted-9H-purines was synthesized and tested for the ability to protect MT4 cells from the cytopathic effect of HIV-1IIIB. These compounds were prepared by a combination of chemical and enzymatic reactions. Some of the nucleoside analogs with
C Bleasdale et al.
Chemical research in toxicology, 6(4), 407-412 (1993-07-01)
(Z,Z)-Muconaldehyde reacts with primary amines, including valine and lysine (epsilon-amino), to afford N-substituted-2-(oxoethyl)pyrroles, which were reduced with sodium borohydride to the more stable N-substituted-2-(hydroxyethyl)pyrroles. The formation of the pyrrole aldehydes was performed in a variety of solvents including aqueous methanol.
Aleksandra Krstulja et al.
Journal of chromatography. A, 1365, 12-18 (2014-09-15)
A series of imprinted polymers targeting nucleoside metabolites, prepared using a template analogue approach, are presented. These were prepared following selection of the optimum functional monomer by solution association studies using (1)H NMR titrations whereby methacrylic acid was shown to

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