Probing the Role of the Mycosamine C2′-OH on the Activity of Amphotericin B

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 enantlomeric series was devoid of activity.