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One-step synthesis of carbohydrate esters as antibacterial and antifungal agents
Bioorganic & Medicinal Chemistry ( IF 3.3 ) Pub Date : 2017-12-26 , DOI: 10.1016/j.bmc.2017.12.038
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.



中文翻译:

一步合成碳水化合物酯作为抗菌和抗真菌剂

碳水化合物酯是可生物降解的,降解的加合物是天然存在的碳水化合物和脂肪酸,对环境无害,对人体无毒。已经开发出单碳水化合物的简单的一步区域选择性酰化,其导致了多种碳水化合物酯的合成。这些酰化碳水化合物的筛选表明,几种化合物对一组细菌和真菌具有活性,包括金黄色葡萄球菌,耐甲氧西林金黄色葡萄球菌(MRSA),白色念珠菌新型隐球菌黄曲霉镰刀菌。。与先前对仅专注于抗菌应用的碳水化合物酯的研究不同,我们的化合物被发现对细菌和真菌均具有活性。此外,合成方法学适合于扩大各种酰化碳水化合物的生产。鉴定出的先导化合物MAN014可以在食品加工和防腐等应用中用作抗菌剂,并用于治疗动植物的细菌和真菌疾病。

更新日期:2017-12-26
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