CAS 15717-45-0

Guanosine, 8-bromo-, 2′,3′,5′-triacetate

Description:

Guanosine, 8-bromo-, 2′,3′,5′-triacetate is a modified nucleoside derivative of guanosine, characterized by the presence of a bromine atom at the 8-position of the purine base and three acetyl groups attached to the hydroxyl groups at the 2′, 3′, and 5′ positions of the ribose sugar. This compound is typically used in biochemical research and synthetic applications due to its structural modifications, which can influence its biological activity and interactions with nucleic acids. The presence of the bromine atom may enhance its reactivity or alter its binding properties compared to unmodified guanosine. The acetylation of the hydroxyl groups serves to increase the lipophilicity of the molecule, potentially facilitating its cellular uptake. As a nucleoside analog, it may also serve as a substrate or inhibitor in enzymatic reactions involving nucleotides. Overall, Guanosine, 8-bromo-, 2′,3′,5′-triacetate is a valuable compound in the study of nucleic acid chemistry and molecular biology.

Formula: C₁₆H₁₈BrN₅O₈

InChI: InChI=1S/C16H18BrN5O8/c1-5(23)27-4-8-10(28-6(2)24)11(29-7(3)25)14(30-8)22-12-9(19-15(22)17)13(26)21-16(18)20-12/h8,10-11,14H,4H2,1-3H3,(H3,18,20,21,26)/t8-,10-,11-,14-/m1/s1

InChI key: InChIKey=JLZCAXCVNVVXJL-IDTAVKCVSA-N

SMILES: BrC=1N(C2=C(N1)C(=O)N=C(N)N2)[C@H]3[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O3

Synonyms:

• 2',3',5'-tri-O-acetyl-8-bromoguanosine
• 2-amino-8-bromo-9-(2,3,5-tri-O-acetylpentofuranosyl)-3,9-dihydro-6H-purin-6-one
• 2′,3′,5′-Tri-O-acetyl-8-bromoguanosine
• 8-Bromo-2′,3′,5′-tri-O-acetylguanosine
• 8-Bromoguanosine 2',3',5'-triacetate
• 8-Bromoguanosine 2′,3′,5′-triacetate
• Guanosine, 8-bromo-, 2′,3′,5′-triacetate
• NSC 174056
• NSC 79210

Guanosine, 8-bromo-, 2',3',5'-triacetate

CAS: 15717-45-0

Formula: C₁₆H₁₈BrN₅O₈

Purity: 95%

Color and Shape: Solid

Molecular weight: 488.2468

Ref: IN-DA001P9M

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-8-bromo-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate

CAS: 15717-45-0

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-8-bromo-6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate

Purity: 95%

Molecular weight: 488.25g/mol

Ref: 54-OR1053498

2'',3'',5''-Tri-O-acetyl-8-bromoadenosine

CAS: 15717-45-0

Formula: C₁₆H₁₈BrN₅O₈

Molecular weight: 488.25

Ref: 7W-GN5696

8-Bromo-2’,3’,5’-tri-O-acetylguanosine-13C2,15N

Controlled Product

CAS: 15717-45-0

Applications 8-Bromo-2’,3’,5’-tri-O-acetylguanosine-13C2,15N is an intermediate in the synthesis of 8-Aminoguanosine-13C2,15N (A609877). 8-Aminoguanosine-13C2,15N is an isotopic labelled compound of 8-Aminoguanosine (A609875), which is a potent inhibitor of purine nucleoside phosphorylase. 8-Bromo-2’,3’,5’-tri-O-acetylguanosine-13C2,15N is also a labelled analog of 8-Bromo-2’,3’,5’-tri-O-acetylguanosine (B688325).
References Kazmers, I.S., et al.: Science, 214, 1137 (1981); Chern, J-W., et al.: J. Med. Chem., 36, 1024 (1993)

Formula: C₂C₁₄H₁₈Br₁₅NN₄O₈

Color and Shape: Neat

Molecular weight: 491.226

Ref: TR-B688327

8-Bromo-2’,3’,5’-tri-O-acetylguanosine

Controlled Product

CAS: 15717-45-0

Applications 8-Bromo-2’,3’,5’-tri-O-acetylguanosine (cas# 15717-45-0) is a compound useful in organic synthesis.
References Kazmers, I.S., et al.: Science, 214, 1137 (1981), Chern, J-W., et al.: J. Med. Chem., 36, 1024 (1993)

Formula: C₁₆H₁₈BrN₅O₈

Color and Shape: Neat

Molecular weight: 488.25

Ref: TR-B688325

2',3',5'-Tri-O-acetyl-8-bromoguanosine

CAS: 15717-45-0

2',3',5'-Tri-O-acetyl-8-bromoguanosine is a synthetic nucleoside analog that inhibits the growth of tumor cells. It has been shown to inhibit the progression of prostate cancer and cervical cancer by binding to guanosine, preventing its conversion into ATP. This compound also prevents proliferation in hek293 and glioblastoma cells. The mechanism of action may be due to oxidative phosphite formation, which causes DNA damage and subsequent apoptosis.

Formula: C₁₆H₁₈BrN₅O₈

Purity: Min. 95%

Color and Shape: Off-White To Light (Or Pale) Yellow Solid

Molecular weight: 488.25 g/mol

Ref: 3D-NT05775