Complex peptidyl nucleoside antibiotics: efficient syntheses of the glycosyl nucleoside amino acid cores.
Employing an amino acid chiral template strategy, the present research describes a general and highly efficient protocol for the rapid construction of enantiopure furanosyl and pyranosyl nucleoside amino acid cores as present in various complex peptidyl nucleoside antibiotics. Starting from easily available d-serine, the strategy and the approach involve rapid and efficient stereoselective synthesis of five- or six-membered lactone amino alcohols, followed by incorporation of the required functionalities of the target molecules on these strategically functionalized chiral templates.
Bhaket
Pushpal
P
Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA.
Stauffer
Christina S
CS
Datta
Apurba
A
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D010455:Peptides; D011692:Puromycin Aminonucleoside / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D010455:Peptides; D011692:Puromycin Aminonucleoside