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Paper | Regular issue | Vol 41, No. 6, 1995, pp.1197-1206
Published online, 1st January, 1970
DOI: 10.3987/COM-94-7007
Mechanism of Formation of Fluorescent Adenosine Analogues

Richard F. de Boer, Daniëlle G. I. Petra, Marin J. Wanner, Aldo Boesaart, and Gerrit-Jan Koomen*

*Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands

Abstract

During studies towards the synthesis of a transition state inhibitor of the enzyme adenylosuccinate lyase, two different pyrimido[2,1-i]purines were found, depending on the reaction conditions. It was shown that one of the products, formed under kinetically controlled reaction conditions can be converted in the thermodynamically more stable one via a Dimroth type rearrangement. The latter isomer shows strong fluorescent properties in the uv/vis region, which makes it potentially useful as a fluorescent probe in biological studies.