Preparation and characterization of NADP derivatives alkylated at 2'-phosphate and 6-amino groups.
Reaction of NADP with 3-propiolactone at pH 6 gave new NADP derivatives carboxyethylated at the 2'-phosphate or 6-amino group, or both: 2'-O-(2-carboxyethyl)phosphono-NAD (I), N6-(2-carboxyethyl)-NADP (II), and 2'-O-(2-carboxyethyl)phosphono-N6-(2-carboxyethyl)-NAD (III). Their structures were assigned on the basis of ultraviolet, 1H-NMR and 31P-NMR spectra, and also treatment with nucleotide pyrophosphatase or alkaline phosphatase. Carbodiimide-promoted reaction of derivative I with 1,2-diaminoethane gave 2'-O-[N-(2-aminoethyl)carbamoylethyl]phosphono-NAD (IV); derivative III gave 2'-O-[N-(2-aminoethyl)carbamoylethyl]phosphono-N6-[N-(2-aminoethyl ) carbamoylethyl]-NAD (IV). The same reaction of derivative II, on the other hand, gave a mixture of N6-[N-(2-aminoethyl)carbamoylethyl]-NADP (Va) and its 3'-phosphate isomer (Vb). The mixture was converted to Va via the 2',3'-cyclic derivative (Vc). Their structures were assigned on the basis of ultraviolet and 1H-NMR spectra, and also treatment with alkaline phosphatase or 3'-nucleotidase. All the NADP derivatives obtained in this work could be reduced with yeast glucose-6-phosphate dehydrogenase.
D000477:Alkylating Agents; D000478:Alkylation; D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D009249:NADP / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011420:Propiolactone; D013056:Spectrophotometry, Ultraviolet
D000477:Alkylating Agents; D009249:NADP; D011420:Propiolactone; C044600:2'-O-(N-(2-aminoethyl)carbamoylethyl)phosphono-NAD; C044601:N(6)-(N-(2-aminoethyl)carbamoyl)NADP; C044602:2'-(O)-(N-(2-aminoethyl)carbamoylethyl)phosphono-N(6)-(N-(2-aminoethyl)carbamoylethyl)NAD