Synthesis of a conformationally locked version of puromycin amino nucleoside.
[reaction: see text] A conformationally locked carbocyclic version of puromycin amino nucleoside was synthesized via Mitsunobu coupling of a 3-azido-substituted carbocyclic moiety with 6-chloropurine without interference from the azido group reacting with triphenylphosphine. The requisite 3-azido-substituted carbocyclic pseudosugar was prepared by a double inversion of configuration at C3' (nucleoside numbering) involving a nucleophilic displacement with azide.
Choi
Yongseok
Y
Laboratory of Medicinal Chemistry, Center for Cancer Research, NCI, Frederick, Maryland 21702, USA.
George
Clifford
C
Strazewski
Peter
P
Marquez
Victor E
VE
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D009705:Nucleosides / Q000737:chemistry; D011691:Puromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D009705:Nucleosides; D011691:Puromycin