Nicotinamide Benzimidazolide Dinucleotides, Non-Cyclisable Analogues of NAD(+)

Benzimidazole-based nucleotides and dinucleotides have been synthesised to increase the range of chemical tools available to probe the NAD(+) biology space. They were examined for their reactivity in alkylation-type reactions, where they yielded unstable alkylated heteoaromatic adducts, both chemica...

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Bibliographic Details
Published inSynlett Vol. 25; no. 16; pp. 2331 - 2336
Main Authors Redpath, Philip, Haluszczak, Jolanta, Macdonald, Simon J., Migaud, Marie E.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.10.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
5-DIPHOSPHATE RIBOSE
CA2+ RELEASE
enzymes
CALCIUM-RELEASE ACTIVITY
MEMBRANE-PERMEANT
benzimidazoribosyl nucleosides
BIOCHEMISCHE EIGENSCHAFTEN
ADENOSINE 5'-DIPHOSPHATE RIBOSE
CYCLIC-ADP-RIBOSE
cyclic adenosine diphosphoribose
CHRONIC LYMPHOCYTIC-LEUKEMIA
CA2+-MOBILIZING ACTIVITY
nucleotides
phosphorylation
DIPHOSPHORIBOSE CADPR
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Summary:Benzimidazole-based nucleotides and dinucleotides have been synthesised to increase the range of chemical tools available to probe the NAD(+) biology space. They were examined for their reactivity in alkylation-type reactions, where they yielded unstable alkylated heteoaromatic adducts, both chemically and enzymatically. While unsuited for NAD(+) cyclases, these NAD(+) analogues could be viable substrates for non-adenine modifying NAD(+)-dependent enzyme classes.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0034-1379000