title: Probing the role of the mycosamine C2'-OH on the activity of amphotericin B.
abstract: A synthetic route to a mycosamine donor was designed and provided access to a set of AmB derivatives targeted to probe the effect of the C2'-OH. It was determined that the configuration of the C2'-position is inconsequential but that O-methylation of this alcohol was deleterious to its mode of action. Additionally, the analog incorporating a mycosamine derivative from the enantiomeric series was devoid of activity.
authors.affiliation: Laboratorium für Organische Chemie, ETH Zürich, CH-8093 Zürich, Switzerland.
authors.forename: Mitchell P
authors.initials: MP
authors.lastname: Croatt
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D000666:Amphotericin B / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D006595:Hexosamines; C014692:mycosamine; D000666:Amphotericin B