A versatile strategy for the synthesis of 4,5-dihydroxy-2,3-pentadione (DPD) and related compounds as potential modulators of bacterial quorum sensing

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Stotani , S , Gatta , V , Medda , F , Padmanaban , M , Karawajzyk , A , Tammela , P S M , Giordanetto , F , Tzalis , D & Collina , S 2018 , ' A versatile strategy for the synthesis of 4,5-dihydroxy-2,3-pentadione (DPD) and related compounds as potential modulators of bacterial quorum sensing ' , Molecules , vol. 23 , no. 10 , 2545 . https://doi.org/10.3390/molecules23102545

Title: A versatile strategy for the synthesis of 4,5-dihydroxy-2,3-pentadione (DPD) and related compounds as potential modulators of bacterial quorum sensing
Author: Stotani, Silvia; Gatta, Viviana; Medda, Federico; Padmanaban, Mohan; Karawajzyk, Anna; Tammela, Päivi Sirpa Marjaana; Giordanetto, Fabrizio; Tzalis, Dimitrios; Collina, Simona
Other contributor: University of Helsinki, Division of Pharmaceutical Biosciences
University of Helsinki, Drug Research Program



Date: 2018-10-06
Language: eng
Number of pages: 22
Belongs to series: Molecules
ISSN: 1420-3049
DOI: https://doi.org/10.3390/molecules23102545
URI: http://hdl.handle.net/10138/276985
Abstract: Resistance to antibiotics is an increasingly serious threat to global public health and its management translates to significant health care costs. The validation of new Gram-negative antibacterial targets as sources for potential new antibiotics remains a challenge for all the scientists working in this field. The interference with bacterial Quorum Sensing (QS) mechanisms represents a potentially interesting approach to control bacterial growth and pursue the next generation of antimicrobials. In this context, our research is focused on the discovery of novel compounds structurally related to (S)-4,5-dihydroxy-2,3-pentanedione, commonly known as (S)-DPD, a small signaling molecule able to modulate bacterial QS in both Gram-negative and Gram-positive bacteria. In this study, a practical and versatile synthesis of racemic DPD is presented. Compared to previously reported syntheses, the proposed strategy is short and robust: it requires only one purification step and avoids the use of expensive or hazardous starting materials as well as the use of specific equipment. It is therefore well suited to the synthesis of derivatives for pharmaceutical research, as demonstrated by four series of novel DPD-related compounds described herein.
Subject: AI-2
AUTOINDUCER-2
COMMUNICATION
DERIVATIVES
DPD
DPD-related compounds
FUTURE PERSPECTIVES
SALMONELLA-TYPHIMURIUM
SIGNAL
SMALL-MOLECULE INHIBITORS
STEREOSELECTIVE-SYNTHESIS
TRIAZOLE
antibiotic resistance
quorum sensing
116 Chemical sciences
1182 Biochemistry, cell and molecular biology
317 Pharmacy
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