Lanthanide Catalyzed Cyclization of Uridine3'-p-Nitrophenyl Phosphate

Authors

M. A. Rishavy
Alvan C. Hengge, Utah State UniversityFollow
W. W. Cleland

Document Type

Article

Journal/Book Title

Bioorganic Chemistry

Publication Date

2000

Volume

28

Issue

5

First Page

283

Last Page

292

Abstract

Steady state kinetics and ¹⁵N isotope effects have been used to study the cyclization reaction of uridine 3′-p-nitrophenyl phosphate. The cyclization reaction is catalyzed by transition metal ions and lanthanides, as are substitution reactions of many phosphate esters. Kinetic analysis reveals that the erbium-catalyzed cyclization reaction involves the concerted deprotonation of the 2′-OH group and departure of the leaving group. The transition state is very late, with a very large degree of bond cleavage to the leaving group, which could be due to a large degree of polarization of the PO bonds by erbium.

Recommended Citation

M. A. Rishavy, A. C. Hengge, and W. W. Cleland . “ Lanthanide Catalyzed Cyclization of Uridine 3'-p-Nitrophenyl Phosphate.” Bioorg.Chem. 2000, 28, (5), 283-292