Synthesis, NMR spectra and chromatographic properties of five trimethylarsonioribosides

Abstract

AbstractFive trimethylarsonioribosides were prepared from naturally occurring and synthetic dimethylarsinylribosides (arsenosugars) by reducing them with 2,3‐dimercaptopropanol and quaternizing the resultant arsine with methyl iodide. The trimethylarsonioribosides prepared in this manner were the four novel compounds methyl 5‐deoxy‐5‐trimethylarsonio‐β‐D‐riboside (as the iodide), (2′R)‐2′, 3′‐dihydroxypropyl 5‐deoxy‐5‐trimethylarsonio‐β‐D‐riboside (as the formate), 3′‐[(2″, 3″ ‐dihydroxypropyl)hydroxyphosphinyloxy] ‐ 2′ ‐hydroxypropyl 5‐deoxy‐5‐trimethylarsonio‐β‐D‐riboside and 3‐(5′‐deoxy‐5′‐trimethylarsonio‐β‐D‐ribosyloxy)‐(2S)‐2‐hydro xypropanesulfonate, and the known (2′S)‐2′‐hydroxy‐3′‐(sulfooxy)propyl 5‐deoxy‐5‐trimethylarsonio‐β‐D‐riboside. They were synthesized to serve as standards for chromatographic analyses of arsenic compounds in marine samples and for investigations into the biotransformation of arsenic in marine organisms. NMR spectral and chromatographic data for the five trimethylarsonioribosides are presented and compared with those of their dimethylarsinyl analogues.