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Angew Chem Int Ed Engl
June 2024
Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, 560-0043, Toyonaka, Osaka, Japan.
Lipopolysaccharide (LPS), a cell surface component of Gram-negative bacteria, activates innate immunity. Its active principle is the terminal glycolipid lipid A. Acetobacter pasteurianus is a Gram-negative bacterium used in the fermentation of traditional Japanese black rice vinegar (kurozu).
View Article and Find Full Text PDFACS Infect Dis
April 2024
Department of Chemistry and Biochemistry, Central Michigan University, Mount Pleasant, Michigan 48859, United States.
Tuberculosis (TB), caused by (Mtb), is the leading cause of death worldwide by infectious disease. Treatment of Mtb infection requires a six-month course of multiple antibiotics, an extremely challenging regimen necessitated by Mtb's ability to form drug-tolerant persister cells. Mtb persister formation is dependent on the trehalose catalytic shift, a stress-responsive metabolic remodeling mechanism in which the disaccharide trehalose is liberated from cell surface glycolipids and repurposed as an internal carbon source to meet energy and redox demands.
View Article and Find Full Text PDFAdv Biol (Weinh)
June 2022
Institute of Microbial Chemistry (BIKAKEN), 3-14-23, Kamiosaki, Shinagawa-ku, Tokyo, 141-0021, Japan.
Nonreducing disaccharide trehalose is used as a stabilizer and humectant in various products and is a potential medicinal drug, showing curative effects on the animal models of various diseases. However, its use is limited as it is hydrolyzed by trehalase, a widely expressed enzyme in multiple organisms. Several trehalose analogs are prepared, including a microbial metabolite 4-trehalosamine, and their high biological stability is confirmed.
View Article and Find Full Text PDFChembiochem
January 2019
Applied Chemistry Department, National Chiao Tung University, 1001, University Road, 300, Hsinchu City, Taiwan.
A general strategy for the diverse synthesis of ten disaccharide aminoglycosides, including natural 2-trehalosamine (1), 3-trehalosamine (2), 4-trehalosamine (3), and neotrehalosyl 3,3'-diamine (8) and synthetic aminoglycosides 4-7, 9, and 10, has been developed. The aminoglycoside compounds feature different anomeric configurations and numbers of amino groups. The key step for the synthesis was the glycosylation coupling of a stereodirecting donor with a configuration-stable TMS glycoside acceptor.
View Article and Find Full Text PDFJ Org Chem
August 2018
Department of Chemistry and Biochemistry , Central Michigan University, Mount Pleasant , Michigan 48859 , United States.
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.
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