One-Step, Nonenzymatic Synthesis of O-Acetyl-ADP-ribose and Analogues from NAD and Carboxylates

O-Acetyl-ADP-ribose (OAADPR) is a metabolite produced from nicotinamide adenine dinucleotide (NAD) as a product of sirtuin-mediated protein deacetylation. We present here a simple, one-step, nonenzymatic synthesis of OAADPR from NAD and sodium acetate in acetic acid. We extended the reaction to othe...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-08, Vol.76 (16), p.6465-6474
Main Authors: Szczepankiewicz, Bruce G, Koppetsch, Karsten J, Perni, Robert B
Format: Article
Language:English
Subjects:
Amino Acid Sequence
Carbohydrates. Nucleosides and nucleotides
Carboxylic Acids - chemistry
Chemistry
Exact sciences and technology
Histone Deacetylases
Molecular Sequence Data
Molecular Structure
NAD - chemistry
NAD - metabolism
Nucleosides, nucleotides and oligonucleotides
O-Acetyl-ADP-Ribose - chemical synthesis
O-Acetyl-ADP-Ribose - chemistry
O-Acetyl-ADP-Ribose - metabolism
Organic chemistry
Preparations and properties
Sirtuin 2 - chemistry
Sirtuin 2 - metabolism
Sirtuins - chemistry
Sirtuins - metabolism
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Summary:O-Acetyl-ADP-ribose (OAADPR) is a metabolite produced from nicotinamide adenine dinucleotide (NAD) as a product of sirtuin-mediated protein deacetylation. We present here a simple, one-step, nonenzymatic synthesis of OAADPR from NAD and sodium acetate in acetic acid. We extended the reaction to other carboxylic acids, demonstrating that the reaction between NAD and nonaqueous carboxylate buffers produces mixtures of the corresponding 2′- and 3′-carboxylic esters.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo2008466