Synthesis of Thiazoloindole α-Amino Acids: Chromophores Amenable to One- and Two-Photon Induced Fluorescence

被引:4
|
作者
Dodds, Amy C. [1 ]
Sansom, Henry G. [1 ]
Magennis, Steven W. [1 ]
Sutherland, Andrew [1 ]
机构
[1] Univ Glasgow, Sch Chem, Glasgow City G12 8QQ, Scotland
基金
英国工程与自然科学研究理事会;
关键词
PROBES; STRATEGIES; PEPTIDE;
D O I
10.1021/acs.orglett.3c03851
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thiazoloindole alpha-amino acids have been synthesized in four steps from tryptophan using a dual-catalytic thiolation reaction and a copper-mediated intramolecular N-arylation process. Late-stage diversification of the thiazoloindole core with electron-deficient aryl substituents produced chromophores that on one-photon excitation displayed blue-green emission, mega-Stokes shifts, and high quantum yields. The thiazoloindole amino acids could also be excited via two-photon absorption in the near-infrared, demonstrating their potential for biomedical imaging applications.
引用
收藏
页码:8942 / 8946
页数:5
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