NOVEL SYNTHETIC OLIGOMERS OF NEISSERIA MENINGITIS SEROGROUP X AND PROCESS OF PREPARING THEM

摘要

The present invention relates to synthesis of novel higher oligomers and process of preparing the same. In particular the present invention relates to the chemical synthesis of oligomers of Neisseria meningitidis serogroup X (‘hereinafter Men-X), more particularly tetramer. The present invention provides Men-X capsular oligomers obtained from synthetic pathway using purified saccharides of specific chain length and provides said novel oligomers as candidates for the development of conjugate vaccine against bacterial meningitis caused due to Men-X infections.

主权项

1. Novel process of synthesizing oligomers, said process comprising the steps of:
synthesizing hemiacetal compd (10) synthesizing propagation unit (12) and terminal unit(s) (14) and (14A) coupling said propagation unit (12) with said terminal unit (14) and coupling said propagation unit (12) with said terminal unit (14A) in the presence of coupling reagents to yield compound (15) and (15A) respectively reacting said compounds (15) and (15A) with deacetylating reagents to obtain compounds (16) and (16A) and then coupling compounds (16) and (16A) using said coupling reagents to obtain compounds (17) and (17A) iterative reactions in the presence of said deacetylating reagents and said coupling reagents to yield novel higher synthetic oligomers (18,18A,19,19A,1,1A,X,XA) one step reduction by reductive N-acetylating reagent, deacetylation using said deacetylating reagents and final deprotection of benzyl and Cbz by hydrogenation, such that said process results in novel higher synthetic oligomers (X) and (XA) with better yield, high purity and enhanced efficacy.