Site-selective chemoenzymatic glycoengineering of Fab and Fc glycans of a therapeutic antibody

Proc Natl Acad Sci U S A. 2018 Nov 20;115(47):12023-12027. doi: 10.1073/pnas.1812833115. Epub 2018 Nov 5.

Abstract

The N-glycans attached to the Fab and Fc domains play distinct roles in modulating the functions of antibodies. However, posttranslational site-selective modifications of glycans in antibodies and other multiply glycosylated proteins remain a challenging task. Here, we report a chemoenzymatic method that permits independent manipulation of the Fab and Fc N-glycans, using cetuximab as a model therapeutic monoclonal antibody. Taking advantage of the substrate specificity of three endoglycosidases (Endo-S, Endo-S2, and Endo-F3) and their glycosynthase mutants, together with an unexpected substrate site-selectivity of a bacterial α1,6-fucosidase from Lactobacillus casei (AlfC), we were able to synthesize an optimal homogeneous glycoform of cetuximab in which the heterogeneous and immunogenic Fab N-glycans were replaced with a single sialylated N-glycan, and the core-fucosylated Fc N-glycans were remodeled with a nonfucosylated and fully galactosylated N-glycan. The glycoengineered cetuximab demonstrated increased affinity for the FcγIIIa receptor and significantly enhanced antibody-dependent cell-mediated cytotoxicity (ADCC) activity.

Keywords: Fc receptor; N-glycan; antibody glycosylation; antibody therapy; glycoengineering.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Antibodies, Monoclonal / chemistry
  • Antibody-Dependent Cell Cytotoxicity / genetics
  • Antibody-Dependent Cell Cytotoxicity / physiology
  • Cetuximab / metabolism
  • Glycoside Hydrolases / metabolism
  • Glycosylation
  • Humans
  • Immunoglobulin Fab Fragments / metabolism*
  • Immunoglobulin Fc Fragments / metabolism*
  • Polysaccharides / metabolism
  • Protein Engineering / methods*
  • Substrate Specificity

Substances

  • Antibodies, Monoclonal
  • Immunoglobulin Fab Fragments
  • Immunoglobulin Fc Fragments
  • Polysaccharides
  • Glycoside Hydrolases
  • Cetuximab