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Improving the fluorescent probe acridonylalanine through a combination of theory and experiment

Sungwienwong, Itthipol and Ferrie, John J. and Jun, Joomyung V. and Liu, Chunxiao and Barrett, Taylor M. and Hostetler, Zachary M. and Ieda, Naoya and Hendricks, Amara and Muthusamy, Anand K. and Kohli, Rahul M. and Chenoweth, David M. and Petersson, George A. and Petersson, E. James (2018) Improving the fluorescent probe acridonylalanine through a combination of theory and experiment. Journal of Physical Organic Chemistry, 31 (8). Art. No. e3813. ISSN 0894-3230. https://resolver.caltech.edu/CaltechAUTHORS:20180822-110219360

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Abstract

Acridonylalanine (Acd) is a useful fluorophore for studying proteins by fluorescence spectroscopy, but it can potentially be improved by being made longer wavelength or brighter. Here, we report the synthesis of Acd core derivatives and their photophysical characterization. We also performed ab initio calculations of the absorption and emission spectra of Acd derivatives, which agree well with experimental measurements. The amino acid aminoacridonylalanine (Aad) was synthesized in forms appropriate for genetic incorporation and peptide synthesis. We show that Aad is a superior Förster resonance energy transfer acceptor to Acd in a peptide cleavage assay and that Aad can be activated by an aminoacyl tRNA synthetase for genetic incorporation. Together, these results show that we can use computation to design enhanced Acd derivatives, which can be used in peptides and proteins.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/poc.3813DOIArticle
ORCID:
AuthorORCID
Ferrie, John J.0000-0001-7934-7266
Petersson, E. James0000-0003-3854-9210
Additional Information:© 2018 John Wiley & Sons, Ltd. Issue Online: 26 July 2018; Version of Record online: 22 February 2018; Manuscript accepted: 27 December 2017; Manuscript received: 15 December 2017. Special Issue: Special issue dedicated to Jack Roberts on the occasion of his 100th birthday. Funding Information: University of Pennsylvania. National Institutes of Health (NIH). Grant Numbers: RR‐023444, RR‐022442, GM‐071399. National Science Foundation (NSF). Grant Numbers: CHE‐1708759, MRI‐0820996, CHE‐1337449, MRI‐1625061, DGE‐1321851. Royal Thai Foundation. Japan Society for the Promotion of Science. Temple University. Gaussian Inc.
Funders:
Funding AgencyGrant Number
University of PennsylvaniaUNSPECIFIED
NIHRR-023444
NIHRR‐022442
NIHGM‐071399
NSFCHE‐1708759
NSFMRI‐0820996
NSFCHE‐1337449
NSFMRI‐1625061
NSFDGE‐1321851
Royal Thai FoundationUNSPECIFIED
Japan Society for the Promotion of Science (JSPS)UNSPECIFIED
Temple UniversityUNSPECIFIED
Gaussian Inc.UNSPECIFIED
Subject Keywords:Acridone; amino acid; electronic structure calculation; fluorescence spectroscopy
Issue or Number:8
Record Number:CaltechAUTHORS:20180822-110219360
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180822-110219360
Official Citation:Sungwienwong I, Ferrie JJ, Jun JV, et al. Improving the fluorescent probe acridonylalanine through a combination of theory and experiment. J Phys Org Chem. 2018;31:e3813. https://doi.org/10.1002/poc.3813
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:89025
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:22 Aug 2018 18:20
Last Modified:03 Oct 2019 20:12

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