Synthesis of pseudo-disaccharide analogues of lipid A: Haptens for the generation of antibodies with glycosidase activity towards lipid A

Berg, R.J.B.H.N. van den; Noort, D.; Marel, G.A. van der; Boom, J.H. van; Benschop, H.P.

Synthesis of pseudo-disaccharide analogues of lipid A: Haptens for the generation of antibodies with glycosidase activity towards lipid A

article

2002

Berg, R.J.B.H.N. van den

Noort, D.

Marel, G.A. van der

Boom, J.H. van

Benschop, H.P.

In order to develop a generic treatment of sepsis caused by infections with Gram-negative bacteria, a series of pseudo-disaccharide analogues of lipid A (1-5) was synthesized. These adducts not only harbor a 2-acylaminodideoxynojirimycin unit mimicking the transition state of the glycosidic hydrolysis, but also a 2-N, 3-O-diacylated glucosamine moiety capable of generating catalytic antibodies with more selective glycosidase properties towards lipid A.

Topics

Catalytic antibody Disaccharide Glucosamine derivative Glycosidase Hapten Lipid A derivative Nojirimycin Antibody production Carbohydrate synthesis Catalysis Enzyme activity Gram negative infection Hydrolysis Sepsis Negibacteria

TNO Identifier

236741

Repository link

https://resolver.tno.nl/uuid:43656342-4c13-41bb-84d1-c84d7a706435

ISSN

07328303

Source

Journal of Carbohydrate Chemistry, 21(3), pp. 167-188.

Pages

167-188

Files

Download berg-2002-synthesis.pdf

Synthesis of pseudo-disaccharide analogues of lipid A: Haptens for the generation of antibodies with glycosidase activity towards lipid A

Make TNO yours!