6533b870fe1ef96bd12cf9dd

RESEARCH PRODUCT

ChemInform Abstract: Chemoselective Removal of Protecting Groups from O-Glycosyl Amino Acid and Peptide (Methoxyethoxy)ethyl Esters Using Lipases and Papain.

Horst KunzDanuta KowalczykJörg EberlingPeter BraunM. Schultz

subject

chemistry.chemical_classificationbiologyPeptideGeneral MedicineGlycopeptideAmino acidPapainchemistry.chemical_compoundchemistryEnzymatic hydrolysisSide chainbiology.proteinOrganic chemistryGlycosylLipase

description

The selective C-terminal deprotection of O-glycopeptide (methoxyethoxy)ethyl esters is achieved under mild conditions (pH 6.6, 37 degrees C) by enzymatic hydrolysis using papain or lipase M from Mucor javanicus to give building blocks useful for chain-extending glycopeptide synthesis. On the other hand, the selective removal of acetyl protecting groups from the saccharide portion of glycopeptides is accomplished by alternative enzymatic hydrolysis with lipase WG from wheat germ to furnish model substrates for enzymatic glycosyl transfer reactions in order to extend the carbohydrate side chain of these conjugates.

https://doi.org/10.1002/chin.199634230