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Synthesis of conformationally locked versions of puromycin analogues.

ABSTRACT: 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.

SUBMITTER: Saneyoshi H

PROVIDER: S-EPMC2765511 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Synthesis of conformationally locked versions of puromycin analogues.

Saneyoshi Hisao H Michel Benoît Y BY Choi Yongseok Y Strazewski Peter P Marquez Victor E VE

The Journal of organic chemistry 20081201 23

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 ...[more]

PMID: 18991379

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