Synthesis of conformationally locked versions of puromycin analogues.
Conformationally locked North and South versions of puromycin analogues built on a bicyclo[3.1.0]hexane pseudosugar template were synthesized. The final assembly of the products was accomplished by the Staudinger-Vilarrasa coupling of the corresponding North (2 and 3) and South (6 and 7) 3'-azidopurine carbanucleosides with the Fmoc-protected 1-hydroxybenzotriazole ester of 4-methoxy-L-tyrosine. North azides 2 and 3 were reported earlier. The 3'-azido intermediates 6 and 7 that are necessary for the synthesis of the South puromycin analogues are described herein for the first time.
Saneyoshi
Hisao
H
Laboratory of Medicinal Chemistry, Center for Cancer Research, NCI-Frederick, Maryland 21702, USA.
Michel
Benoît Y
BY
Choi
Yongseok
Y
Strazewski
Peter
P
Marquez
Victor E
VE
D000964:Antimetabolites, Antineoplastic / Q000138:chemical synthesis / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D008956:Models, Chemical; D008968:Molecular Conformation; D009705:Nucleosides / Q000737:chemistry; D010455:Peptides / Q000737:chemistry; D011691:Puromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D012343:RNA, Transfer / Q000737:chemistry; D012270:Ribosomes / Q000737:chemistry
D000964:Antimetabolites, Antineoplastic; D009705:Nucleosides; D010455:Peptides; D011691:Puromycin; D012343:RNA, Transfer