Collect. Czech. Chem. Commun. 1996, 61, 1538-1548

"Abbreviated" NAD+ Analogues Containinga Phosphonate Function

Dana Hocková, Milena Masojídková and Antonín Holý

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


"Abbreviated" NAD+ analogues with anionic phosphonate function as a part of the link between the adenine and nicotinamide moieties, 9-(2-phosphonomethoxyethyl)adenine 2-(3-carbamoylpyridinium)ethyl ester (1a), (R)- and (S)-9-(2-phosphonomethoxypropyl)adenine 2-(3-carbamoylpyridinium)ethyl ester (1b and 1c), (RS)-9-(3-hydroxy-2-phosphonomethoxypropyl)adenine 2-(3-carbamoylpyridinium)ethyl ester (1d), and (S)- and (R)-1-[3-(adenin-9-yl)-2-phosphonatomethoxypropyl]-3-carbamoylpyridinium (2a and 2b), were prepared by multistep syntheses using the Zincke reaction in the last step.

Keywords: NAD+ analogues; Phosphonate nucleotide analogues; Zincke reaction.