A synthetic GFP-like chromophore undergoes base-catalyzed autoxidation into acylimine red form

Pavel E. Ivashkin, Konstantin A. Lukyanov, Sergey Lukyanov, Ilia V. Yampolsky

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Fluorescent proteins are widely used in modern experimental biology, but much controversy exists regarding details of maturation of different types of their chromophores. Here we studied possible mechanisms of DsRed-type red chromophore formation using synthetic biomimetic GFP-like chromophores, bearing an acylamino substituent, corresponding to an amino acid residue at position 65. We have shown these model compounds to readily react with molecular oxygen to produce a highly unstable DsRed-like acylimine, isolated in the form of stable derivatives. Under the same aerobic conditions an unusual red-shifted imide chromophore - a product of 4-electron oxidation of Gly65 residue - is formed. Our data showed that GFP chromophore is prone to autoxidation at position 65 Cα by its chemical nature with basic conditions being the only key factor required.

Original languageEnglish
Pages (from-to)2782-2791
Number of pages10
JournalJournal of Organic Chemistry
Volume76
Issue number8
DOIs
Publication statusPublished - 15 Apr 2011
Externally publishedYes

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