Global ETD Search
Search theses and dissertations gathered from participating repositories worldwide. Every result links back to the library that holds it. No account is needed.
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Showing 1 to 6 of 6 for “"mycosamine"”.
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Synthesis and function of the conserved motif of mycosamine-containing polyene macrolides
Mycosamine-containing polyene macrolides represent a large family of natural products with antifungal activity, of which amphotericin B (AmB) is an important member. Several of these clinically vital but toxic agents have been proposed to exert their biological activity through ion channel …
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Elucidation of the mycosamine dependent sterol binding and antifungal activities of amphotericin B
… for deletion were the carboxylic acid and the mycosamine sugar appendages. Both of these functional groups had been predicted to be critical for the following roles: 1) stabilizing ion channel formation via an intermolecular salt-bridge interaction, 2) anchoring AmB to phospholipid bilayers and …
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Electronic tuning of site selectivity and semisynthesis of C2'-deoxyamphotericin B
… interactions involving the carboxylic acid and mycosamine appendages of AmB have been predicted to play important roles in the mechanism. To investigate the mode of action of AmB, derivatives of AmB lacking one or both of these appendages were synthesized and submitted to biophysical assays to …
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A synthesis enabled understanding of Amphotericin B leading to derivatives with improved therapeutic indices
… cells by binding and extracting sterols in a mycosamine dependent fashion. Additionally, the C2’-OH and C3’-NH3+ are critical residues on the mycosamine appendage, which are responsible for stabilizing a conformation that allows for the binding of both ergosterol and cholesterol. When either …
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Methods to enable the detection of targeted AmphDI glycosyltransferase mutants that transfer GDP-C2’epimycosamine to amphoteronolide
… of the aglycone acceptor AmdeB with GDP-mycosamine in the biosynthesis of AmB. Using the reverse glycosylation reaction, we identified robust detecting of deglycosylation product amphoternolide (AmdeB) using AmB as starting material. Unfortunately, C2’epiAmB was not accepted by AmphDI and …
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Slow-release cross-coupling and an advanced method for β-glycosylation: methods stimulated by amphotericin B
… 1,2-cis glycosidic bond found in AmB a mycosamine sugar donor synthesis was developed incorporating a new directing group for neighboring group participation. The use of this new directing group enabled efficient glycosylation of, and ultimately the completion of, a critical building …