Stereoselective Synthesis of 6-Amln0-5,6dideoxy-D-ribo-heptafuranouronates with the Aid of Glycine. Chiral Templates

Abstract

Our current interest in developing peptido-nucleosides, e.g. sinefungin derivatives as potential inhibitors of Leishmania parasite growth, 1 and homologues of polyoxins and neopolyoxins as prototypes of “low charge” nucleotide analogues, has prompted us to investigate synthetic methods for the enantioselective preparation of 6-amino-5.6dideoxy-D-ribo-heptafuranouro as key intermediates. Sinefungin, a nucleoside antibiotic, is a potent inhibitor of S-adenosylmethionine (SAM)-dependent methylases, and is very similar structurally to SAM.1 Polyoxins, uracil nucleosides containing a peptide moiety, mimic anionic N-acetylglwosyl-uridine 5′-diphOsphate and are powerful competitive inhibitors of chitin UDP-N acetylglucosoamine-transferase.2