Secondary modification of oxidatively-modified proline N-termini for the construction of complex bioconjugates

Johnathan C Maza; Alexandra V Ramsey; Meire Mehare; Shane W Krska; Craig A Parish; Matthew B Francis

doi:10.1039/d0ob00211a

Secondary modification of oxidatively-modified proline N-termini for the construction of complex bioconjugates

Org Biomol Chem. 2020 Mar 14;18(10):1881-1885. doi: 10.1039/d0ob00211a. Epub 2020 Feb 26.

Authors

Johnathan C Maza¹, Alexandra V Ramsey¹, Meire Mehare¹, Shane W Krska², Craig A Parish², Matthew B Francis³

Affiliations

¹ Department of Chemistry, University of California, Berkeley, California 94720, USA. mbfrancis@berkeley.edu.
² Discovery Chemistry, Merck & Co., Inc., Kenilworth, New Jersey 07033, USA.
³ Department of Chemistry, University of California, Berkeley, California 94720, USA. mbfrancis@berkeley.edu and Materials Science Division, Lawrence Berkeley National Laboratories, Berkeley, California 94720, USA.

Abstract

A convenient two-step method is reported for the ligation of alkoxyamine- or hydrazine-bearing cargo to proline N-termini. Using this approach, bifunctional proline N-terminal bioconjugates are constructed and proline N-terminal proteins are immobilized.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Amines / chemistry*
Hydrazines / chemistry*
Hydrazones / chemical synthesis
Ketones / chemical synthesis
Oxidation-Reduction
Oximes / chemical synthesis
Proline / chemistry*
Proteins / chemical synthesis*
Pyrococcus furiosus / chemistry
Tobacco Mosaic Virus / chemistry

Substances

Amines
Hydrazines
Hydrazones
Ketones
Oximes
Proteins
Proline

Grants and funding

T32 GM066698/GM/NIGMS NIH HHS/United States