Synthesis of Novel Spin-Labeled Photoaffinity Derivatives of NAD+ and ATP and Their Characterization as Coenzymes and Substrates of Several Enzymes

Michael S. Seiter; Michael P. Bauer; Pia D. Vogel; Wolfgang E. Trommer

doi:10.1055/s-1996-4181

Synthesis 1996; 1996(2): 269-273
DOI: 10.1055/s-1996-4181

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Synthesis of Novel Spin-Labeled Photoaffinity Derivatives of NAD⁺ and ATP and Their Characterization as Coenzymes and Substrates of Several Enzymes

Michael S. Seiter, Michael P. Bauer, Pia D. Vogel, Wolfgang E. Trommer^*

^*Fachbereich Chemie der Universität Kaiserslautern, Erwin Schrödinger Str., D-67663 Kaiserslautern, Germany, Fax +49(631)2053419

Abstract

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The synthesis of an NAD⁺ derivative (2-N₃-N⁶-SL-NAD⁺) and the corresponding ATP analog (2-N₃-N⁶-SL-ATP) is described, where a spin label (SL) (2,2,6,6-tetramethyl-piperidine-1-yloxy radical, tempamine) is attached to the N⁶-position and an azido function to the C2-atom of the adenine ring. Both compounds were shown to be active coenzymes or substrates for various enzymes and could be covalently incorporated into the enzymes upon irradiation (photoaffinity labeling). In complex with the appropriate enzymes, the compounds exhibited ESR spectra typical for highly immobilized, enzyme-bound radicals. The starting compound in both cases was 2,6-dichloro-9-β-D-ribofuranosylpurine. Through the synthesis of 2-N₃-N⁶-SL-AMP, a general intermediate is presented for the synthesis of a variety of nucleotides that have substitutions at the N⁶- and the 2-position of the adenine-moiety.

adenine nucleotide analogs - NAD analogs - spin labeling - photoaffinity labeling

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