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

ABSTRACT: Trehalosamine (2-amino-2-deoxy-?,?-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.

SUBMITTER: Groenevelt JM

PROVIDER: S-EPMC6358420 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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

Groenevelt Jessica M JM Meints Lisa M LM Stothard Alicyn I AI Poston Anne W AW Fiolek Taylor J TJ Finocchietti David H DH Mulholand Victoria M VM Woodruff Peter J PJ Swarts Benjamin M BM

The Journal of organic chemistry 20180723 15

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 succes ...[more]

PMID: 29973045

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