Collect. Czech. Chem. Commun. 1995, 60, 237-250

Synthesis of Base-Modified "Abbreviated" NAD Analogues

Kristina Juricováa, Svatava Smrčkováa and Antonín Holýb

a Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


The "abbreviated" model of NAD, 1-[3-(adenin-9-yl)-2-hydroxypropyl]-3-carbamoylpyridinium chloride (VIIIa), and its 2,6-diaminopurine (VIIIb), 3-deazaadenine (VIIIc), guanine (VIIId) and cytosine (VIIIe) analogues were prepared by the Zincke reaction. The (R)-isomer of the adenine model VIIIa (compound IX) was prepared for chiroptical studies. As shown by NMR, UV and CD spectra, neither in dimethyl sulfoxide nor in water any intramolecular π-π interactions exist between the heteroaromatic systems.