Zwitterionization of capsular saccharides

Details Zwitterionization of capsular saccharides Zwitterionization of capsular saccharides

A - Human Necessities

61

K

A61K 39/09 (2006.01) C08B 37/00 (2006.01)

Patent

CA 2620416

Capsular saccharides are typically anionic. In the invention, however, cationic groups are introduced, such that the modified saccharide has a repeating unit which includes both cationic and anionic groups. These cationic and anionic groups can be balanced to give a zwitterionic repeating unit. These modifications can convert a saccharide that is normally a T-independent antigen into one that can activate T cells without requiring conjugation to a carrier. Typically, the invention modifies an anionic bacterial capsular saccharide antigen by converting a neutral group in the saccharide into a cationic group e.g. to change -NHAc to -NH3 +.

Les saccharides capsulaires sont typiquement anioniques. Néanmoins dans l'invention on introduit des groupes cationiques pour que le saccharide modifié comporte une unité répétitive incluant à la fois des groupes cationiques et anioniques. Ces groupes anioniques et cationiques peuvent être équilibrés pour donner une unité zwittérionique répétitive. Ces modifications peuvent convertir un saccharide qui est normalement un antigène T indépendant en un antigène activateur de cellules T sans nécessiter de le conjuguer à un porteur. Typiquement, l'invention modifie un antigène anionique bactérien de saccharide capsulaire en convertissant un groupe neutre du saccharide en un groupe cationique, par exemple en changeant -NHAc en -NH3 +.

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