Selective and reversible photochemical derivatization of cysteine residues in peptides and proteinsElectronic supplementary information (ESI) available: Experimental procedures, preparation and NMR spectra of newly synthesized compounds. See DOI: 10.1039/c3sc51691a

The 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 a 350 nm fluorescent lamp. NQMP can be conjugated with various moieties, such as PEG, dy...

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Main Authors: Arumugam, Selvanathan, Guo, Jun, Mbua, Ngalle Eric, Friscourt, Frédéric, Lin, Nannan, Nekongo, Emmanuel, Boons, Geert-Jan, Popik, Vladimir V
Format: Article
Language:English
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Summary:The 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 a 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 a low equivalence of the reagent. The NQMP-thioether linkage is stable under ambient conditions, and survives protein digestion and MS analysis. Irradiation of an NQMP-labeled protein in a dilute solution (
ISSN:2041-6520
2041-6539
DOI:10.1039/c3sc51691a