A Comparative Proton Magnetic Resonance Study of the Molecular Conformation of Uracil and 6-Aza Uracil Nucleosides and Nucleotides

1973 ◽  
Vol 51 (15) ◽  
pp. 2571-2577 ◽  
Author(s):  
Donald J. Wood ◽  
Frank E. Hruska ◽  
Richard J. Mynott ◽  
Ramaswamy H. Sarma

Proton magnetic resonance data for uridine and uridine-5′-monophosphate, and the corresponding 6-azauracil analogs, are presented and discussed in terms of their overall three dimensional conformations in aqueous solution. The data reveal a destabilizing influence of the 6-aza base upon the gog and g′–g′ conformation of the ribose phosphate moiety.


1991 ◽  
Vol 69 (7) ◽  
pp. 1156-1160 ◽  
Author(s):  
Tahar Lakhlifi ◽  
Ahmed Sedqui ◽  
Bernard Laude ◽  
Nguyen Dinh An ◽  
Joël Vebrel

Three azomethine ylide precursors including the methyl 3,4-dihydro-6,7-dimethoxyisoquinoline-3carboxylate moiety were synthesized. The 1,3-dipolar species formed from these products react with activated dipolarophilic olefines leading diastereospecifically to derivatives of 4′,5′-dimethoxy-1,2-benzo-4,7-imino-4-methoxycarbonyl-1-cycloheptene. Proton magnetic resonance data allowed the determination of the stereochemistry of the cycloadducts. Key words: cyclic azomethine ylide, azabicyclic compounds, stereochemistry.



1973 ◽  
Vol 51 (7) ◽  
pp. 1099-1106 ◽  
Author(s):  
Frank E. Hruska ◽  
Alan Mak ◽  
Harwant Singh ◽  
David Shugar

The 100- and 220- MHz p.m.r. spectra of uridine, cytidine, and their 2′-O-methyl derivatives are obtained in aqueous solution at several temperatures. The experimental chemical shifts and coupling constants are discussed in terms of the overall molecular conformation. The conclusion is reached that 2′-O-methylation has little effect upon the three-dimensional structure of a nucleoside at the monomer level in an aqueous environment.



1968 ◽  
Vol 90 (17) ◽  
pp. 4583-4585 ◽  
Author(s):  
John F. Deters ◽  
Patrick A. McCusker ◽  
Richard C. Pilger


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