Synthesis and characterization of fluorescent amino acid dimethylaminoacridonylalanine

Fluorescent amino acids are powerful biophysical tools as they can be used in structural or imaging studies of a given protein without significantly perturbing its native fold or function. Here, we have synthesized and characterized 7-(dimethylamino)acridon-2-ylalanine (Dad), a red-shifted derivativ...

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Published inARKIVOC free online journal of organic chemistry Vol. 2021; no. 5; pp. 97 - 109
Main Authors Jones, Chloe M, Petersson, George A, Petersson, E James
Format Journal Article
LanguageEnglish
Published Switzerland 01.01.2021
Subjects
Fluorescence
acridone
unnatural amino acid
twisted intramolecular charge transfer
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Summary:Fluorescent amino acids are powerful biophysical tools as they can be used in structural or imaging studies of a given protein without significantly perturbing its native fold or function. Here, we have synthesized and characterized 7-(dimethylamino)acridon-2-ylalanine (Dad), a red-shifted derivative of the genetically-incorporable amino acid, acridon-2-ylalanine. Alkylation increases the quantum yield and fluorescence lifetime of Dad relative to a previously published amino acid, 7-aminoacridon-2-ylalanine (Aad). These properties of Dad make it a potentially valuable protein label, and we have performed initial testing of its ability to be genetically incorporated using an evolved aminoacyl tRNA synthetase.
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We are pleased to dedicate this article to Prof. Peter A. Jacobi, longtime colleague of George A. Petersson at Wesleyan University and teacher of E. James Petersson at Dartmouth College.
ISSN:1551-7012
1551-7004
1551-7012
DOI:10.24820/ARK.5550190.P011.498