101491-32-1Relevant articles and documents
Chemoenzymatic Synthesis of Trehalosamine, an Aminoglycoside Antibiotic and Precursor to Mycobacterial Imaging Probes
Groenevelt, Jessica M.,Meints, Lisa M.,Stothard, Alicyn I.,Poston, Anne W.,Fiolek, Taylor J.,Finocchietti, David H.,Mulholand, Victoria M.,Woodruff, Peter J.,Swarts, Benjamin M.
, p. 8662 - 8667 (2018)
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.
Visualization of mycobacterial membrane dynamics in live cells
Rodriguez-Rivera, Frances P.,Zhou, Xiaoxue,Theriot, Julie A.,Bertozzi, Carolyn R.
, p. 3488 - 3495 (2017)
Mycobacteria are endowed with a highly impermeable mycomembrane that confers intrinsic resistance to many antibiotics. Several unique mycomembrane glycolipids have been isolated and structurally characterized, but the underlying organization and dynamics of glycolipids within the cell envelope remain poorly understood. We report here a study of mycomembrane dynamics that was enabled by trehalose-fluorophore conjugates capable of labeling trehalose glycolipids in live actinomycetes. We identified fluorescein-trehalose analogues that are metabolically incorporated into the trehalose mycolates of representative Mycobacterium, Corynebacterium, Nocardia, and Rhodococcus species. Using these probes, we studied the mobilities of labeled glycolipids by time-lapse microscopy and fluorescence recovery after photobleaching experiments and found that mycomembrane fluidity varies widely across species and correlates with mycolic acid structure. Finally, we discovered that treatment of mycobacteria with ethambutol, a front-line tuberculosis (TB) drug, significantly increases mycomembrane fluidity. These findings enhance our understanding of mycobacterial cell envelope structure and dynamics and have implications for development of TB drug cocktails.
The Synthesis of α-D-Galactopyranosyl and α-D-Mannopyranosyl 2-Amino-2-deoxy-α-D-glucopyranosides and the Conformation of Their Glycoside Linkage
Koto, Shinkiti,Inada, Shigeru,Zen, Shonosuke
, p. 2728 - 2734 (2007/10/02)
A new analog of trehalosamine, α-D-galactopyranosyl 2-amino-2-deoxy-α-D-glucopyranoside, was synthesized by the glycosylation of 2,3,4,6-tetra-O-(p-chlorobenzyl)-α-D-galactopyranose with 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl
