Journal
ORGANIC LETTERS
Volume 23, Issue 11, Pages 4137-4141Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01013
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Funding
- National Natural Science Foundation of China [21778068, 21977111, 22007096]
- Shenzhen Science and Technology Innovation Commission [JCYJ20170818153538196, JCYJ20170413165916608]
- Natural Science Foundation of Guangdong Province [2019A1515012073, 2018B030308001]
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An efficient approach to preparing azobenzene functionalized peptides through late-stage modification of tyrosine-containing peptides using a dearomatization-rearomatization strategy was reported. This method demonstrates good chemoselectivity, site selectivity, and sensitivity to various peptides, enriching the postsynthetic modification toolbox of peptides and showing great potential for applications in medicinal chemistry and chemical biology.
Azobenzene functionalized peptides are of great importance in photoresponsive biosystems and photopharmacology. Herein, we report an efficient approach to prepare azobenzene functionalized peptides through late-stage modification of tyrosine-containing peptides using a dearomatization-rearomatization strategy. This approach shows good chemoselectivity and site selectivity as well as sensitive group tolerance to various peptides. This method enriches the postsynthetic modification toolbox of peptides and has great potential to be applied in medicinal chemistry and chemical biology.
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