Synthesis of a conformationally locked version of puromycin amino nucleoside

Yongseok Choi, Clifford George, Peter Strazewski, Victor E. Marquez

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

(formula presented) 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.

Original languageEnglish
Pages (from-to)589-592
Number of pages4
JournalOrganic Letters
Volume4
Issue number4
DOIs
Publication statusPublished - 2002 Feb 21
Externally publishedYes

Fingerprint

Puromycin
nucleosides
Nucleosides
Carbasugars
Azides
synthesis
inversions
interference
configurations
carbocyclic puromycin
triphenylphosphine
6-chloropurine

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Synthesis of a conformationally locked version of puromycin amino nucleoside. / Choi, Yongseok; George, Clifford; Strazewski, Peter; Marquez, Victor E.

In: Organic Letters, Vol. 4, No. 4, 21.02.2002, p. 589-592.

Research output: Contribution to journalArticle

Choi, Yongseok ; George, Clifford ; Strazewski, Peter ; Marquez, Victor E. / Synthesis of a conformationally locked version of puromycin amino nucleoside. In: Organic Letters. 2002 ; Vol. 4, No. 4. pp. 589-592.
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