CaltechAUTHORS
Published August 2018 | Version Supplemental Material
Journal Article Open

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

Creators

  • 1. ROR icon University of Pennsylvania
  • 2. ROR icon China Agricultural University
  • 3. ROR icon Nagoya City University
  • 4. ROR icon Temple University

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.

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.

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Supplemental Material - poc3813-sup-0001-data_s1.pdf

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poc3813-sup-0001-data_s1.pdf

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Additional details

Identifiers

Eprint ID
89025
Resolver ID
CaltechAUTHORS:20180822-110219360

Funding

University of Pennsylvania
NIH
RR-023444
NIH
RR‐022442
NIH
GM‐071399
NSF
CHE‐1708759
NSF
MRI‐0820996
NSF
CHE‐1337449
NSF
MRI‐1625061
NSF
DGE‐1321851
Royal Thai Foundation
Japan Society for the Promotion of Science (JSPS)
Temple University
Gaussian Inc.

Dates

Created
2018-08-22
Created from EPrint's datestamp field
Updated
2021-11-16
Created from EPrint's last_modified field