An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing

OS Ascenso, JC Marques, AR Santos, KB Xavier…

Index: Ascenso, Osvaldo S.; Marques, Joao C.; Santos, Ana Rita; Xavier, Karina B.; Rita Ventura; Maycock, Christopher D. Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 3 p. 1236 - 1241

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Citation Number: 16

Abstract

Autoinducer-2 (AI-2) is a signalling molecule for bacterial inter-species communication. A synthesis of (S)-4, 5-dihydroxypentane-2, 3-dione (DPD), the precursor of AI-2, is described starting from methyl glycolate. The key step was an asymmetric reduction of a ketone with (S)-Alpine borane. This new method was highly reproducible affording DPD for biological tests without contaminants. The biological activity was tested with the previously available ...