Oxygen chiral phosphodiesters-8. Stereochemical course of the base-catalyzed hydrolysis of cyclic 2'-deoxyadenosine 3',5'-[17O, 18O]monophosphate

Shujaath Mehdi, Jeffrey A. Coderre, John A. Gerlt

Research output: Contribution to journalArticlepeer-review

Abstract

At 100° and in 0.2 M Ba(OH)2 the Rp diastereomer of cyclic 2'-deoxyadenosine 3',5' -[17O, 18O]monophosphate is hydrolyzed to a 4:1 mixture of the Sp diastereomer of 3' -[16O, 17O, 18O]dAMP and the Rp diastereomer of 5' -[16O, 17O, 18O]dAMP, respectively, demonstrating that the hydrolysis reaction is accompanied by complete inversion of configuration at phosphorus. This finding establishes that pseudorotation of pentacoordinate reaction intermediates is unimportant in this chemical hydrolysis reaction.

Original languageEnglish (US)
Pages (from-to)3483-3492
Number of pages10
JournalTetrahedron
Volume39
Issue number21
DOIs
StatePublished - 1983
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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