Open AccessPreparation and characterization of NADP derivatives alkylated at 2′‐phosphate and 6‐amino groups
Author(s) -
OKUDA Keiko,
SUNTINANALERTS Prasert,
MIYOSHI Shinsuke,
URABE Itaru,
YAMADA Yasuhiro,
OKADA Hirosuke
Publication year - 1985
Publication title -
european journal of biochemistry
Language(s) - English
Resource type - Journals
eISSN - 1432-1033
pISSN - 0014-2956
DOI - 10.1111/j.1432-1033.1985.tb08743.x
Subject(s) - chemistry , nad+ kinase , dehydrogenase , stereochemistry , derivative (finance) , phosphate , nucleotide , medicinal chemistry , enzyme , organic chemistry , biochemistry , financial economics , economics , gene
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), N 6 ‐(2‐carboxyethyl)‐NADP (II), and 2′‐ O ‐(2‐carboxyethyl)phosphono‐ N 6 ‐(2‐carboxyethyl)‐NAD (III). Their structures were assigned on the basis of ultraviolet, 1 H‐NMR and 31 P‐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‐ N 6 ‐[ N ‐(2‐aminoethyl)carbamoylethyl]‐NAD (VI). The same reaction of derivative II, on the other hand, gave a mixture of N 6 ‐[ N ‐[ 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 1 H‐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.