One-step Synthesis of Carbohydrate Esters as Antibacterial and Antifungal Agents

Publication date: Available online 26 December 2017
Source:Bioorganic & Medicinal Chemistry
Author(s): Madher N. AlFindee, Qian Zhang, Yagya Prasad Subedi, Jaya P. Shrestha, Yukie Kawasaki, Michelle Grilley, Jon Y. Takemoto, Cheng-Wei Tom Chang
Carbohydrate esters are biodegradable, and the degraded adducts are naturally occurring carbohydrates and fatty acids which are environmentally friendly and non-toxic to human. A simple one-step regioselective acylation of mono-carbohydrates has been developed that leads to the synthesis of a wide range of carbohydrate esters. Screening of these acylated carbohydrates revealed that several compounds were active against a panel of bacteria and fungi, including Staphylococcus aureus. methicillin-resistant S. aureus (MRSA), Candida albicans, Cryptococcus neoformans, Aspergillus flavus and Fusarium graminearum. Unlike prior studies on carbohydrate esters that focus only on antibacterial applications, our compounds are found to be active against both bacteria and fungi. Furthermore, the synthetic methodology is suitable to scale-up production for a variety of acylated carbohydrates. The identified lead compound, MAN014, can be used as an antimicrobial in applications such as food processing and preservation and for treatment of bacterial and fungal diseases in animals and plants.

Graphical abstract

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