Selective and Reversible Photochemical Derivatization of Cysteine Residues in Peptides and Proteins.
Selective derivatization of solvent-exposed cysteine residues in peptides and proteins is achieved by brief irradiation of an aqueous solution containing 3-(hydroxymethyl)-2-naphthol derivatives (NQMPs) with 350 nm fluorescent lamp. NQMP can be conjugated with various moieties, such as PEG, dyes, carbohydrates, or possess a fragment for further selective derivatization, e.g., biotin, azide, alkyne, etc. Attractive features of this labeling approach include an exceptionally fast rate of the reaction and a requirement for low equivalence of the reagent. The NQMP-thioether linkage is stable under ambient conditions, survives protein digestion and MS analysis. Irradiation of NQMP-labeled protein in a dilute solution (<40 μM) or in the presence of a vinyl ether results in a traceless release of the substrate. The reversible biotinylation of bovine serum albumin, as well as capture and release of this protein using NeutrAvidin Agarose resin beads has been demonstrated.
Department of Chemistry, University of Georgia, Athens, GA 30602, USA.
Selvanathan
S
Arumugam
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602, USA.
Jun
J
Guo
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602, USA.
Ngalle Eric
NE
Mbua
Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602, USA.
Frédéric
F
Friscourt
Department of Chemistry, University of Georgia, Athens, GA 30602, USA.
Nannan
N
Lin
Department of Chemistry, University of Georgia, Athens, GA 30602, USA.
Emmanuel
E
Nekongo
Department of Chemistry, University of Georgia, Athens, GA 30602, USA ; Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602, USA.
Geert-Jan
GJ
Boons
Department of Chemistry, University of Georgia, Athens, GA 30602, USA.
Vladimir V
VV
Popik