Chemoenzymatic Approach toward the Synthesis of 3-O-(?/?)-Glucosylated 3-Hydroxy-?-lactams.

ABSTRACT: Glycosylation significantly alters the biological and physicochemical properties of small molecules. ?-Lactam alcohols comprise eligible substrates for such a transformation based on their distinct relevance in the chemical and medicinal community. In this framework, the unprecedented enzymatic glycosylation of the rigid and highly strained four-membered ?-lactam azaheterocycle was studied. For this purpose, cis-3-hydroxy-?-lactams were efficiently prepared in three steps by means of a classical organic synthesis approach, while a biocatalytic step was implemented for the selective formation of the corresponding 3-O-?- and -?-glucosides, hence overcoming the complexities typically encountered in synthetic glycochemistry and contributing to the increasing demand for sustainable processes in the framework of green chemistry. Two carbohydrate-active enzymes were selected based on their broad acceptor specificity and subsequently applied for the ?- or ?-selective formation of ?-lactam-sugar adducts, using sucrose as a glucosyl donor.

SUBMITTER: Decuyper L 

PROVIDER: S-EPMC6289546 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature