title: Phosphonoxins III: synthesis of α-aminophosphonate analogs of antifungal polyoxins with anti-Giardia activity.
abstract: A synthesis of α-aminophosphonate analogs of polyoxins, termed phosphonoxin C1, C2, and C3, has been achieved. The key step was the addition of lithium dimethyl phosphite to the aldehyde of a protected threose derivative. α-Hydroxyphosphonate analogs C4 and C5 were also obtained by taking advantage of an unprecedented conversion of an azide to hydroxyl during treatment with hydrogen on palladium on carbon. The resulting phosphonoxin C5 inhibited the growth of an intestinal protozoan, Giardia lamblia, at low micromolar concentration.
authors.affiliation: Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, USA.
authors.forename: Michael
authors.initials: M
authors.lastname: Staake
authors.forename: Jay
authors.initials: J
authors.lastname: Chauhan
authors.forename: Ding
authors.initials: D
authors.lastname: Zhou
authors.forename: Aaron
authors.initials: A
authors.lastname: Shanker
authors.forename: Atasi
authors.initials: A
authors.lastname: De Chatterjee
authors.forename: Siddhartha
authors.initials: S
authors.lastname: Das
authors.forename: Steven E
authors.initials: SE
authors.lastname: Patterson
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D016829:Giardia lamblia / Q000187:drug effects*; D015394:Molecular Structure; D063065:Organophosphonates; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000935:Antifungal Agents; D063065:Organophosphonates; D011741:Pyrimidine Nucleosides; C002457:polyoxin