Preparation of glucosaminyl muramic acid derivatives

Details Preparation of glucosaminyl muramic acid derivatives Preparation of glucosaminyl muramic acid derivatives

C - Chemistry, Metallurgy

07

H

C07H 15/18 (2006.01) C07H 15/00 (2006.01) C07H 15/04 (2006.01) C07K 9/00 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2231505

The present invention provides a method for the preparation of disaccharides, such as glucosaminyl muramic acids peptides and derivatives. The method includes condensing a protected muramic acid ester with a 1-organothio- or 1- fluoroglucosamine derivative in the presence of a suitable promoter to produce a protected glucosaminyl muramic acid ester. The protected glucosaminyl muramic acid ester may be used to prepare disaccharide peptides, such as N- acetylglucosaminyl-N-acetylmuramyl dipeptides, which have demonstrated immunological activity. Protected muramic acid esters and 1-organothio- or 1- fluoro-glucosamine compounds which may be employed as intermediates in the method are also provided.

L'invention concerne un procédé de préparation de disaccharides, tels que des peptides et des dérivés d'acide muramique de glucosaminyle. Ce procédé consiste à condenser un ester protégé d'acide muramique avec un dérivé de 1-organothio- ou 1-fluoroglucosamine en présence d'un promoteur approprié, de manière à obtenir un ester protégé d'acide muramique de glucosaminyle. On peut utiliser cet ester protégé afin de préparer des peptides de disaccharides, tels que des dipeptides de N-acétylglucosaminyl-N-acétylmuramyle, qui se sont avérés présenter une activité immunologique. L'invention concerne également des esters protégés d'acide muramique et des composés de 1-organothio- ou 1-fluoroglucosamine que l'on peut utiliser en tant qu'intermédiaires dans le procédé.

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