Syntheses and Configurational Analyses of Thymidine 4-Nitrophenyl [17O,18OJPhosphates and the Stereochemical Course of a Reaction Catalyzed by Bovine Pancreatic Deoxyribonuclease I

John A. Gerlt, Shujaath Mehdi

Research output: Contribution to journalArticlepeer-review

Abstract

The syntheses of both diastereomers of thymidine 3,-(4-nitrophenyl [O, 18O]phosphate) ([O, 0]TpNP) and of thymidine 5′-(4-nitrophenyl [17O,l8O]phosphate) ([17O, 18O]NPpT) and the.Rp diastereomer of thymidine 3 -(4-nitrophenyl [17O, 18O]phosphate) 5 -(4-nitrophenyl phosphate) ([17O,18O]NPpTpNP) are described. The absolute configurations of the chiral phosphorus atoms have been determined unambiguously by 31P and 17O NMR spectroscopy. The RP diastereomer of [17O,18O]NPpTpNP was hydrolyzed in the presence of bovine pancreatic deoxyribonuclease I to yield the RP diastereomer of thymidine 3′-[16O, 17O, 18O]-phosphate 5 -(4-nitrophenyl phosphate), demonstrating that the enzyme-catalyzed reaction occurs by a mechanism in which a single displacement reaction occurs at the chiral phosphorus atom.

Original languageEnglish (US)
Pages (from-to)4844-4852
Number of pages9
JournalBiochemistry
Volume23
Issue number21
DOIs
StatePublished - Oct 1984
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry

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