Versatile 1H-31P-31P COSY 2D NMR Techniques for the Characterization of Polyphosphorylated Small Molecules

Ananya Majumdar, Yan Sun, Meha Shah, Caren L. Freel Meyers

Research output: Contribution to journalArticlepeer-review

Abstract

Di- and triphosphorylated small molecules represent key intermediates in a wide range of biological and chemical processes. The importance of polyphosphorylated species in biology and medicine underscores the need to develop methods for the detection and characterization of this compound class. We have reported two-dimensional HPP-COSY spectroscopy techniques to identify diphosphate-containing metabolic intermediates at submillimolar concentrations in the methylerythritol phosphate (MEP) isoprenoid biosynthetic pathway.(1)In this work, we explore the scope of HPP-COSY-based techniques to characterize a diverse group of small organic molecules bearing di- and triphosphorylated moieties. These include molecules containing P-O-P and P-C-P connectivities, multivalent P(III)-O-P(V) phosphorus nuclei with widely separated chemical shifts, as well as virtually overlapping 31P resonances exhibiting strong coupling effects. We also demonstrate the utility of these experiments to rapidly distinguish between mono- and diphosphates. A detailed protocol for optimizing these experiments to achieve best performance is presented.

Original languageEnglish (US)
Pages (from-to)3214-3223
Number of pages10
JournalJournal of Organic Chemistry
Volume75
Issue number10
DOIs
StatePublished - May 21 2010

ASJC Scopus subject areas

  • Organic Chemistry

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