Chemoenzymatic Synthesis of Trehalosamine, an Aminoglycoside Antibiotic and Precursor to Mycobacterial Imaging Probes
| Autor: | Taylor J. Fiolek, Anne W. Poston, Lisa M. Meints, Victoria M Mulholand, Jessica M. Groenevelt, Peter J. Woodruff, Alicyn I Stothard, Benjamin M. Swarts, David H Finocchietti |
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| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Glycosylation
Chemistry Techniques Synthetic 010402 general chemistry 01 natural sciences Chemical synthesis Article Mycobacterium tuberculosis chemistry.chemical_compound biology 010405 organic chemistry Organic Chemistry Aminoglycoside Amino Sugars biology.organism_classification Antimicrobial 0104 chemical sciences Anti-Bacterial Agents Molecular Imaging Transformation (genetics) chemistry Biochemistry Biocatalysis Glucosyltransferases Molecular imaging |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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