Synthesis of Fluorescent Dibenzofuran α-Amino Acids: Conformationally Rigid Analogues of Tyrosine
Liyao Zeng
1, 2
,
Olivia Marshall
1, 2
,
Rochelle Mcgrory
1, 2
,
Rebecca Clarke
1, 2
,
Ryan Brown
1, 2
,
Malcolm Kadodwala
1, 2
,
Andrew R Thomson
1, 2
,
A B Sutherland
1, 2
1
School of Chemistry, The Joseph Black Building, Glasgow, United Kingdom
|
Publication type: Journal Article
Publication date: 2025-03-03
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
Abstract
We report two synthetic strategies for the preparation of dibenzofuran α-amino acids, expanding the structural toolbox of fluorescent probes. The strategies involved dibenzofuran synthesis via a Pd(II)-catalyzed C–O cyclization, alongside an efficient Negishi coupling approach for faster access to analogues. These rigid tyrosine mimics possess enhanced fluorescent properties compared to proteinogenic amino acids as demonstrated by application of the lead compound as a FRET donor for monitoring peptide hydrolysis by a serine protease.
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Zeng L. et al. Synthesis of Fluorescent Dibenzofuran α-Amino Acids: Conformationally Rigid Analogues of Tyrosine // Organic Letters. 2025. Vol. 27. No. 10. pp. 2475-2479.
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Zeng L., Marshall O., Mcgrory R., Clarke R., Brown R., Kadodwala M., Thomson A. R., Sutherland A. B. Synthesis of Fluorescent Dibenzofuran α-Amino Acids: Conformationally Rigid Analogues of Tyrosine // Organic Letters. 2025. Vol. 27. No. 10. pp. 2475-2479.
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TY - JOUR
DO - 10.1021/acs.orglett.5c00433
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.5c00433
TI - Synthesis of Fluorescent Dibenzofuran α-Amino Acids: Conformationally Rigid Analogues of Tyrosine
T2 - Organic Letters
AU - Zeng, Liyao
AU - Marshall, Olivia
AU - Mcgrory, Rochelle
AU - Clarke, Rebecca
AU - Brown, Ryan
AU - Kadodwala, Malcolm
AU - Thomson, Andrew R
AU - Sutherland, A B
PY - 2025
DA - 2025/03/03
PB - American Chemical Society (ACS)
SP - 2475-2479
IS - 10
VL - 27
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2025_Zeng,
author = {Liyao Zeng and Olivia Marshall and Rochelle Mcgrory and Rebecca Clarke and Ryan Brown and Malcolm Kadodwala and Andrew R Thomson and A B Sutherland},
title = {Synthesis of Fluorescent Dibenzofuran α-Amino Acids: Conformationally Rigid Analogues of Tyrosine},
journal = {Organic Letters},
year = {2025},
volume = {27},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.5c00433},
number = {10},
pages = {2475--2479},
doi = {10.1021/acs.orglett.5c00433}
}
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MLA
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Zeng, Liyao, et al. “Synthesis of Fluorescent Dibenzofuran α-Amino Acids: Conformationally Rigid Analogues of Tyrosine.” Organic Letters, vol. 27, no. 10, Mar. 2025, pp. 2475-2479. https://pubs.acs.org/doi/10.1021/acs.orglett.5c00433.