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Photochemical Probes in Biochemistry pp 277–296Cite as

‘CAGED’ Compounds to Probe the Dynamics of Cellular Processes: Synthesis and Properties of some Novel Photosensitive P-2-Nitrobenzyl Esters of Nucleotides

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Part of the book series: NATO ASI Series ((ASIC,volume 272))

Abstract

Photochemical release of substrates or regulatory molecules is a developing technique that overcomes problems such as diffusional delays in the kinetic study of biological processes involving macromolecular assemblies. A wide range of phosphate esters such as nucleotides and nucleotide analogues can be alkylated on their phosphate groups with 1-(2-nitrophenyl)diazoethane and l-(3,4- dimethoxy-6-nitrophenyl)diazoethane. The phosphate esters so formed are generally biologically inert and may be photolyzed to starting material with near-UV (300-360 nm) irradiation. Flash photolysis of these ‘caged’ compounds with a pulsed laser or arc lamp releases up to several millimolar of a biologically active compound. Subsequent to photon absorption, dark reactions occur within the caged compounds before the active compound is released and measurement of the rate of these processes is necessary to determine the time resolution of the technique. P-l-(2-Nitrophenyl)ethyl esters of nucleoside 3′,5′-cyclic phosphates photolyze at 5 s∓1 at 21°C in aqueous solution at pH 7 and 11 M ionic strength. Below pH 7 the photolysis is acid catalyzed. P-l-(3,4-dimethoxy-6-nitrophenyl)ethyl esters of Pi and ATP photolyze more slowly than the corresponding P-l-(2-nitrophenyl)ethyl esters. The P-1-(3,4-dimethoxy-6-nitrophenyl)ethyl esters of cyclic nucleotides are unstable in water at pH 7. However the P-l-(3,4- dimethoxy-6-nitrobenzyl)esters of cyclic nucleotides appear to photolyze more rapidly than their P-1-(2-nitrobenzyl)ester counterparts, though with low quantum yield. The implications of these results for the photolysis mechanisms and the application of 2- nitrobenzyl phosphate esters in biological research is discussed.

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Author information

Authors and Affiliations

  1. Department of Physiology, College of Veterinary Medicine, Cornell University, 14853, Ithaca, NY, USA

    John F. Wootton

  2. Division of Physical Biochemistry, National Institute for Medical Research, Mill Hill, NW7 1AA, London, UK

    David R. Trentham

Authors
  1. John F. Wootton
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  2. David R. Trentham
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Editors and Affiliations

  1. Department of Biochemistry B, University of Copenhagen The Panum Institute, Blegdamsvej 3c, 2200, Copenhagen, Denmark

    Peter E. Nielsen

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© 1989 Kluwer Academic Publishers

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Wootton, J.F., Trentham, D.R. (1989). ‘CAGED’ Compounds to Probe the Dynamics of Cellular Processes: Synthesis and Properties of some Novel Photosensitive P-2-Nitrobenzyl Esters of Nucleotides. In: Nielsen, P.E. (eds) Photochemical Probes in Biochemistry. NATO ASI Series, vol 272. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0925-0_21

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  • DOI: https://doi.org/10.1007/978-94-009-0925-0_21

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-6905-2

  • Online ISBN: 978-94-009-0925-0

  • eBook Packages: Springer Book Archive

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