Methods for making saccharide-protein glycoconjugates

The invention provides a process for the reductive amination of a carbonyl group at the reducing terminus of a polysaccharide, wherein the reductive amination is carried out at a pH between 4 and 5. The invention also provides a process for preparing a conjugate of a polysaccharide and a carrier mol...

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Bibliographic Details
Main Authors Saul, Allan James, Micoli, Francesca
Format Patent
LanguageEnglish
Published 16.06.2020
Subjects
CHEMISTRY
COMPOSITIONS BASED THEREON
DERIVATIVES THEREOF
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
ORGANIC MACROMOLECULAR COMPOUNDS
PEPTIDES
POLYSACCHARIDES
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
THEIR PREPARATION OR CHEMICAL WORKING-UP
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Summary:The invention provides a process for the reductive amination of a carbonyl group at the reducing terminus of a polysaccharide, wherein the reductive amination is carried out at a pH between 4 and 5. The invention also provides a process for preparing a conjugate of a polysaccharide and a carrier molecule, comprising the steps of: (a) coupling the polysaccharide to a linker, to form a polysaccharide-linker compound in which the free terminus of the linker is an ester group; and (b) reacting the ester group with a primary amine group in the carrier molecule, to form a polysaccharide-linker-carrier molecule conjugate in which the linker is coupled to the carrier molecule via an amide linkage. The invention also provides a process for reducing contamination of a polysaccharide-linker compound with unreacted linker, comprising a step of precipitating unreacted linker under aqueous conditions at a pH of less than 5. The invention also provides polysaccharide-linker-carrier molecule conjugates and intermediate compounds obtained or obtainable by these processes.
Bibliography:Application Number: US201815977754