A Versatile Strategy for the Synthesis of 4,5-Dihydroxy-2,3-Pentanedione (DPD) and Related Compounds as Potential Modulators of Bacterial Quorum Sensing

Silvia Stotani, Viviana Gatta, Federico Medda, Mohan Padmanaban, Anna Karawajczyk, Päivi Tammela, Fabrizio Giordanetto, Dimitrios Tzalis and Simona Collina

Molecules 2018, 23, 2545  doi:10.3390/molecules23102545;

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.

Want to know more about this publication?

Contact our scientists

medicinal chemistry

Drug Discovery

We are running our own state-of-the-art Drug Discovery Chemistry facilities in Germany with the option for process research chemistry, upscaling, kilolab production…

performance chemicals

Material Science

We create performance chemicals to enhance new materials, plastics, coatings, dyes & inks, cosmetics, flavors and many more research and industrial applications…


Looks interesting?

As a leading contract research organization in discovery chemistry and custom synthesis, Taros provides comprehensive solutions to meet our clients’ needs from diverse branches and applications

Our experienced chemists practice a pragmatic culture and customer-centric approach in order to exceed project expectations, despite challenges, bridging very narrow timelines. They are trained to consider economic, safety and ecological boundaries and conditions laid out for all stages of the project, starting from the development of synthetic routes to…