33359-03-4

Usage

InChI:InChI=1/C9H9N5O/c1-5-3-14-8(15)6-7(11-4-10-6)13(2)9(14)12-5/h3-4H,1-2H3,(H,10,11)

Upstream product

• 52662-10-9 3,4-Dihydro-4,6-dimethyl-3-β-D-ribofuranosyl-9H-imidazo<1,2-a>purin-9-one 
• 76542-73-9 5-(N-cyanomethylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide 
• 83325-57-9 1-Benzyl-5-(cyano-methyl-amino)-1H-imidazole-4-carboxylic acid amide 
• 83325-58-0 9-benzyl-3-methylguanine 
• 76473-15-9 1-benzyl-5-(methylamino)-1H-imidazole-4-carboxamide 
• 68768-26-3 5-(methylamino)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 69265-28-7 5-(cyanomethylamino)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 2958-98-7 3-methylguanine 
• 65120-78-7 7-benzyl-3-methylguanine 
• 70230-72-7 5-(methylamino)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide 
• 68768-32-1 3-methylguanosine 
• 598-31-2 1-bromoacetone 
• 65120-81-2 1-benzyl-4,6-dimethyl-1,4-dihydro-imidazo[1,2-a]purin-9-one 

Relevant academic research and scientific papers

Hydrolysis of Nucleosides Related to Wyosine

The glycosidic bond of 3-β-D-ribofuranosylwye (1) has been found to undergo not only hydrogen ion catalysed cleavage but also general base catalysed or nucleophilic cleavage; steric assistance has been shown to account for its unusual susceptibility to acid.

Facile, general and productive syntheses of the fluorescent wye (4,9-dihydro-4,6-dimethyl-9-oxo-1H-imidazo[1,2-a]purine) in phenylalanine tRNA, its 2-substituted derivatives and 7-aza analogues

Novel syntheses of 4,9-dihydro-4,6-dimethyl-9-oxo-1 H-imidazo[1,2-a]purine (Y base skeleton), its 2-substituted derivatives and 7-aza analogues and their fluorescence characteristics in relation to their structures are described.

Studies towards the synthesis of the fluorescent bases of phenylalanine transfer ribonucleic acids: synthesis of 7-methylwye isolated from extremely thermophilic archaebacteria.

Acid- or base-catalyzed acylation of 1-benzylwye (7) provided the 7-substituted derivatives 9, 10, and 11 in poor yields. Although the reactions of lithiated 7 with electrophiles gave the 2-substituted derivatives 14, 15, 17, 20, 21, and 22, lithiation of

Synthesis of 3-β-D-Ribofuranosylwye, the Most Probable Structure for Wyosine from Torulopsis utilis Phenylalanine Transfer Ribonucleic Acid

Treatment of 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide (5a) with CNBr in acetate buffer gave the 5-cyanomethylamino derivative 6a, which was cyclized to 3-methyl-guanosine (7) in the presence of NaOEt.Cyclocondensation of 7 with bromoacetone in the presence of K2CO3 provided 3-β-D-ribofuranosylwye (2), the most probable strucure for the fluorescent nucleoside from Torulopsis utilis phenylalanine transfer ribonucleic acid (tRNAPHE).The glycosidic bonds of 2 and 7 have been shown to be unusually subject to cleavage under either acidic or basic conditions, but proved to be less labile under neutral conditions, as had been reported.The base moiety of 2 is also cleaved under basic conditions.Keywords--wyosine; 3-methylguanosine; cyclocondensation; imidazole nucleoside; N-cyanation; base-catalyzed cyclization; glycosidic bond cleavage; ring fission

SYNTHESIS OF 3,9-DIALKYLGUANINES AND THEIR CONVERSION INTO 3-ALKYLWYES, MODELS FOR THE FLUORESCENT NUCLEOSIDES FROM PHENYLALANINE TRANSFER RIBONUCLEIC ACIDS

Synthesis of 3,9-dialkylguanines 5 has been accomplished by N-cyanation of 1-alkyl-5-(alkylamino)imidazole-4-carboxamides 3 followed by base-catalysed cyclisation.Cyclocondensation of 9-alkyl-3-methylguanines 5a, d, f with MeCOCH2Br gave 3-alkylwyes 6, model compounds of the most probable structure for wyosine from Torulopsis utilis tRNAPhe.

A Simple Synthesis of 3-β-D-Ribofuranosylwye and the Stability of its Glycosidic Bond

Treatment of 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide (3) with CNBr followed by cyclization and reaction with bromoacetone gave 3-β-D-ribofuranosylwye (2) whose glycosidic bond was cleaved rapidly in acidic or alkaline solution, but was fairly stable at pH 5-8.5 at 37 deg C.