Solid-Phase Synthesis of Fluorinated Analogues of Glycosyl 1-Phosphate Repeating Structures from Leishmania using the Phosphoramidite Method.

Abstract

Bacterial and protozoan sugar chains contain glycosyl 1‐phosphate repeating structures; these repeating structures have been studied for vaccine development. The fluorinated analogues of [β‐Gal‐(1→4)‐α‐Man‐(1→6)‐P‐]n, which are glycosyl 1‐phosphate repeating structures found in Leishmania, were synthesised using the solid‐phase phosphoramidite method. This method has been less extensively studied for the synthesis of glycosyl 1‐phosphate units than H‐phosphonate chemistry. A stepwise synthesis of a compound containing five such repeating units has been conducted using the phosphoramidite method herein, which is the longest glycosyl 1‐phosphate structures to be chemically constructed in a stepwise manner.