Site-selective C-C modification of proteins at neutral pH using organocatalyst-mediated cross aldol ligations.

ABSTRACT: The bioconjugation of proteins with small molecules has proved an invaluable strategy for probing and perturbing biological mechanisms. The general use of chemical methods for protein functionalisation can be limited however by the requirement for complicated reaction partners to be present in large excess, and harsh conditions which are incompatible with many protein scaffolds. Herein we describe a site-selective organocatalyst-mediated protein aldol ligation (OPAL) that affords stable carbon-carbon linked bioconjugates at neutral pH. OPAL enables rapid modification of proteins using simple aldehyde probes in minimal excess, and is utilised here in the affinity tagging of proteins in cell lysate. Furthermore we demonstrate that the β-hydroxy aldehyde OPAL product can be functionalised aga

SUBMITTER: Spears RJ 

PROVIDER: S-EPMC6049525 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature