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Facile Hydrogen-Deuterium Exchange at the 5′-Position of an Analogue of S-Adenosyl-l-methionine

✍ Scribed by Olafur Th. Magnusson; Perry A. Frey

Publisher
Elsevier Science
Year
2002
Tongue
English
Weight
161 KB
Volume
30
Category
Article
ISSN
0045-2068

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✦ Synopsis

S-3Ј,4Ј-anhydroadenosyl-L-methionine is an analogue of the S-adenosyl-L-methionine coenzyme. Here we report on a rapid solvent exchange of the methylene protons at the 5Ј-position of this analogue. The rate of H/D exchange was measured by nuclear magnetic resonance spectroscopy under buffered conditions in deuterium oxide. The reaction is specific base catalyzed and displays a second-order rate constant of 2 ϫ 10 4 M Ϫ1 s Ϫ1 , which corresponds to a rate enhancement of 10 12 compared to solvent exchange of ␣ -methylene protons in acyclic, aliphatic sulfonium ions. No other carbon bonded hydrogens in the molecule exchange with solvent under the experimental conditions. Allylic stabilization of a carbanionic-like transition state for the solvent exchange process can account for these results. Solvent exchange under these mild conditions provides a simple way to prepare a 5Ј-2 H-labeled form of the coenzyme analogue. ᭧ 2002 Elsevier Science (USA)

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S-adenosyl-L-homocysteine (AdoHcy) is an important metabolic product in a variety of processes (1.2). This compound as well as 5'-methylthioadenosine are substrates for AdoHcy nucleosidase. an enzyme required In various prokaryotes cells (3.4.5.6) for the recovery of the enzymatic activity of methyl