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Synthesis and enzymatic evaluation of the guanosine analogue 2-amino-6-mercapto-7-methylpurine ribonucleoside (MESG): insights into the phosphorolysis reaction mechanism based on the blueprint transition state: SN1 or SN2?

Synthesis and enzymatic evaluation of the guanosine analogue 2-amino-6-mercapto-7-methylpurine ribonucleoside (MESG): insights into the phosphorolysis reaction mechanism based on the blueprint transition state: SN1 or SN2?

Neto, Brenno A.D., Lapis, Alexandre A.M., Netz, Paulo A., Spencer, John, Dias, Silvio L.P., Tamborim, Silvia M., Basso, Luiz A., Santos, Diógenes S. and Dupont, Jairton (2010) Synthesis and enzymatic evaluation of the guanosine analogue 2-amino-6-mercapto-7-methylpurine ribonucleoside (MESG): insights into the phosphorolysis reaction mechanism based on the blueprint transition state: SN1 or SN2? Journal of the Brazilian Chemical Society, 21 (1). pp. 151-156. ISSN 0103-5053 (Print), 1678-4790 (Online) (doi:https://doi.org/10.1590/S0103-50532010000100022)

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Abstract

A modified experimental procedure for the synthesis of MESG (2-amino-6-mercapto-7-methylpurine ribonucleoside) 1 has been successfully performed and its full characterization is presented. High resolution ESI(+)-MSMS indicates both the nucleoside bond cleavage as the main fragmentation in the gas phase and a possible SN1 mechanism. Ab initio transition state calculations based on the blue print transition state support this mechanistic rationale and discard an alternative SN2 mechanism. Assays using purine nucleoside phosphorylase (PNP) enzyme (human and M. tuberculosis sources) indicate its efficiency in the phosphorolysis of MESG and allow the quantitative determination of inorganic phosphate in real time assay.

Item Type: Article
Additional Information: [1] Open Access. All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License (http://creativecommons.org/licenses/by-nc/4.0/deed.en).
Uncontrolled Keywords: MESG, PNP enzyme, ESI, tuberculosis
Subjects: Q Science > QD Chemistry
Faculty / Department / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Related URLs:
Last Modified: 30 Jan 2020 12:30
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
Selected for GREAT 2019: None
URI: http://gala.gre.ac.uk/id/eprint/2084

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