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

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

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

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.

Original languageEnglish
Pages (from-to)8662-8667
Number of pages6
JournalJournal of Organic Chemistry
Volume83
Issue number15
DOIs
StatePublished - Aug 3 2018

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