A Synthetic GFP-like Chromophore Undergoes Base-Catalyzed Autoxidation into Acylimine Red Form

作者：Ivashkin Pavel E; Lukyanov Konstantin A; Lukyanov Sergey; Yampolsky Ilia V^*

来源：Journal of Organic Chemistry, 2011, 76(8): 2782-2791.

DOI：10.1021/jo200150b

Fluorescent proteins are widely used in modem 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 C alpha by its chemical nature with basic conditions being the only key factor required.

• 出版日期2011-4-15