Chemoenzymatic Synthesis of Trehalosamine, an Aminoglycoside Antibiotic and Precursor to Mycobacterial Imaging Probes

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2018 Jul 6

PMID 29973045

Citations 9

Authors

Jessica M Groenevelt

Lisa M Meints

Alicyn I Stothard

Anne W Poston

Taylor J Fiolek

David H Finocchietti

Victoria M Mulholand

Peter J Woodruff

Benjamin M Swarts

Affiliations

Soon will be listed here.

Abstract

Trehalosamine (2-amino-2-deoxy-α,α-d-trehalose) is an aminoglycoside with antimicrobial activity against Mycobacterium tuberculosis, and it is also a versatile synthetic intermediate used to access imaging probes for mycobacteria. To overcome inefficient chemical synthesis approaches, we report a two-step chemoenzymatic synthesis of trehalosamine that features trehalose synthase (TreT)-catalyzed glycosylation as the key transformation. Soluble and recyclable immobilized forms of TreT were successfully employed. We demonstrate that chemoenzymatically synthesized trehalosamine can be elaborated to two complementary imaging probes, which label mycobacteria via distinct pathways.

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