Expanding the Pyrimidine Diphosphosugar Repertoire: The Chemoenzymatic Synthesis of Amino- and Acetamidoglucopyranosyl Derivatives

Jiqing Jiang; John B Biggins; Jon S Thorson

doi:10.1002/1521-3773(20010417)40:8<1502::AID-ANIE1502>3.0.CO;2-K

Expanding the Pyrimidine Diphosphosugar Repertoire: The Chemoenzymatic Synthesis of Amino- and Acetamidoglucopyranosyl Derivatives

Angew Chem Int Ed Engl. 2001 Apr 17;40(8):1502-1505. doi: 10.1002/1521-3773(20010417)40:8<1502::AID-ANIE1502>3.0.CO;2-K.

Authors

Jiqing Jiang¹, John B Biggins¹, Jon S Thorson¹

Affiliation

¹ Laboratory for Biosynthetic Chemistry Memorial Sloan-Kettering Cancer Center 1275 York Avenue, Box 309, New York, NY 10021 (USA) Fax: (+1) 212-717-3066 and The Sloan-Kettering Division Joan and Sanford I. Weill Graduate School of Medical Sciences Cornell University.

PMID: 29712364
DOI: 10.1002/1521-3773(20010417)40:8<1502::AID-ANIE1502>3.0.CO;2-K

Abstract

The exploitation of a unique thymidylyltransferase (E_p ) allows the rapid syntheses of thymidine and uridine 5'-(aminodeoxy-α-D-hexopyranosyl diphosphates), 5'-(acetamidodeoxy-α-D-hexopyranosyl diphosphates), and even 5'-(aminodideoxy-α-D-hexopyranosyl diphosphates), which are amino analogues of the products from the native reaction of E_p .

Keywords: enzyme catalysis; glycosyl phosphate; nucleotides; synthetic methods; transferases.