Nicotinamide Benzimidazolide Dinucleotides, Non-Cyclisable Analogues of NAD+

Philip Redpath; Jolanta Haluszczak; Simon J. Macdonald; Marie E. Migaud

doi:10.1055/s-0034-1379000

Nicotinamide Benzimidazolide Dinucleotides, Non-Cyclisable Analogues of NAD⁺

Philip Redpath, Jolanta Haluszczak, Simon J. Macdonald, Marie E. Migaud

Research output: Contribution to journal › Article › peer-review

270 Downloads (Pure)

Abstract

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.

Original language	English
Pages (from-to)	2331-2336
Journal	Synlett
Volume	25
Issue number	16
Early online date	26 Aug 2014
DOIs	https://doi.org/10.1055/s-0034-1379000
Publication status	Published - 2014

Keywords

benzimidazoribosyl nucleosides
cyclic adenosine diphosphoribose
enzymes
nucleotides
phosphorylation

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-0034-1379000

lNettiercotinamide Benzimidazolide Dinucleotides, Non-Cyclisable Analogues ofFinal published version, 218 KB

Fingerprint Dive into the research topics of 'Nicotinamide Benzimidazolide Dinucleotides, Non-Cyclisable Analogues of NAD<sup>+</sup>'. Together they form a unique fingerprint.

Cite this

@article{7ce0441f49304718bce1b608a988b6cb,

title = "Nicotinamide Benzimidazolide Dinucleotides, Non-Cyclisable Analogues of NAD+",

abstract = "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.",

keywords = "benzimidazoribosyl nucleosides, cyclic adenosine diphosphoribose, enzymes, nucleotides, phosphorylation",

author = "Philip Redpath and Jolanta Haluszczak and Macdonald, {Simon J.} and Migaud, {Marie E.}",

year = "2014",

doi = "10.1055/s-0034-1379000",

language = "English",

volume = "25",

pages = "2331--2336",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "16",

}

TY - JOUR

T1 - Nicotinamide Benzimidazolide Dinucleotides, Non-Cyclisable Analogues of NAD+

AU - Redpath, Philip

AU - Haluszczak, Jolanta

AU - Macdonald, Simon J.

AU - Migaud, Marie E.

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

KW - benzimidazoribosyl nucleosides

KW - cyclic adenosine diphosphoribose

KW - enzymes

KW - nucleotides

KW - phosphorylation

U2 - 10.1055/s-0034-1379000

DO - 10.1055/s-0034-1379000

M3 - Article

VL - 25

SP - 2331

EP - 2336

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 16

ER -