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Studies on nucleotides and related compounds in plants. IV. Synthesis of N 6 ‐benzyladenosine phosphate derivatives of possible relevance to starch grain formation
Author(s) -
Duncan H. J.
Publication year - 1973
Publication title -
journal of the science of food and agriculture
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.782
H-Index - 142
eISSN - 1097-0010
pISSN - 0022-5142
DOI - 10.1002/jsfa.2740240113
Subject(s) - nucleotide , chemistry , phosphate , nucleoside , sugar phosphates , adenine nucleotide , methanol , biosynthesis , dephosphorylation , starch , cellulose , aqueous solution , biochemistry , ammonium carbonate , hydrolysis , ammonium acetate , mannose , ammonium , organic chemistry , nuclear chemistry , phosphatase , enzyme , high performance liquid chromatography , gene
The chemical synthesis of gramme quantities of a range of N 6 ‐substituted adenine nucleotides (cytokinins) required primarily for studies on starch grain biosynthesis is undertaken. The direct conversion of preformed samples of AMP, ADP, ATP, ADP‐ N ‐acetylglucosamine and ADP‐mannose is successfully accomplished in yields ranging from 19 to 35% using DEAE‐cellulose and 70% aqueous methanol solutions of ammonium carbonate for their isolation from original nucleotide material. For the synthesis of N 6 ‐benzylADP‐α‐glucose and N 6 ‐benzylADP‐β‐glucose recourse had to be made to the morpholidate procedure and the products were thus obtained in yields of 42 to 48% as isolated from DEAE‐cellulose with 70% aqueous methanol solutions of ammonium acetate at pH 5. The substituted adenine compounds were treated with the potato tuber preparation shown previously, to mobilise adenine from a range of adenine nucleotides. As with other nucleotides tested dephosphorylation readily occurred, but cleavage of the nucleoside releasing N 6 ‐substituted adenine could not be detected, thus emphasising the specificity of the adenyl‐cleaving activity of the potato tuber preparation.