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850926

2′,3′,5′-Tri-O-acetylguanosine

Name: 2′,3′,5′-Tri-<I>O</I>-acetylguanosine
Brand: ALDRICH

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

NACRES:

NA.22

PubChem Substance ID:

24888303

UNSPSC Code:

12352123

EC Number:

230-242-4

MDL number:

MFCD00057054

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Properties

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

Description

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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A novel nitroimidazole compound formed during the reaction of peroxynitrite with 2',3',5'-tri-O-acetyl-guanosine.

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

Reactions of muconaldehyde isomers with nucleophiles including tri-O-acetylguanosine: formation of 1,2-disubstituted pyrroles from reactions of the (Z,Z)-isomer with primary amines.

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.

Effect of isobutylmethylxanthine and related drugs on the receptor response (ERG; a-wave) of the frog retina at various extracellular calcium concentrations.

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

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Global Trade Item Number

SKU	GTIN
850926-1G	04061826708071
850926-5G	04061833341247