A concise synthesis of α-D-ribofuranosyl alkylphosphonates — Putative substrate intermediates for the carbon–phosphorous lyase system

Abstract

Carbon–phosphorous lyase is a multienzyme system found in many species of bacteria that is distinguished by its ability to hydrolyze a broad array of unactivated alkylphosphonates. α-D-Ribofuranosyl alkylphosphonates are potential metabolic intermediates generated by the carbon–phosphorous lyase pathway. Here we describe a facile synthesis of α-D-ribofuranosyl alkylphosphonates using β-D-ribofuranosyl trichloracetimidate as a glycosyl donor.Key words: carbon–phosphorous lyase, phn operon, phnN, phosphonates, glycosyl trichloroacetimidate donor, α-D-ribofuranosyl ethylphosphonate.