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Synlett 2021; 32(14): 1371-1378
DOI: 10.1055/a-1479-6366
DOI: 10.1055/a-1479-6366
synpacts
Targeting Tryptophan for Tagging through Photoinduced Electron Transfer
Funding for this work was provided by the Department of Chemistry and by the Wyoming Sensory Biology COBRE program (5P20GM121310-02).
Abstract
The chemical modification of tryptophan (Trp) has been the subject of interest for nearly 100 years, yet the development of modification conditions that exploit the inherent photolability of Trp has remained elusive. With this perspective, we discuss our recently reported method for Trp photobioconjugation that uses N-carbamoyl pyridinium salts to engage Trp in photoinduced electron transfer. We detail our inspiration and rationale, and we place our report in the context of selected prior art in the field.
1 Introduction
2 Light Activation as a Design Principle in Bioconjugation
3 Targeting Tryptophan with Light
4 Reaction Design and Proof of Concept
5 Mechanistic Considerations
6 Establishing Mechanistic Control
7 Conclusions and Outlook
Publication History
Received: 24 March 2021
Accepted after revision: 11 April 2021
Accepted Manuscript online:
11 April 2021
Article published online:
05 May 2021
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For general reviews, see:
For selected examples of aromatic amino acid modification, see:
For selected examples of cysteine modification, see:
For carboxylate activation, see:
For reviews on pyridinium salt chemistry see:
For select examples, see: