Late Stage Phosphotyrosine Mimetic Functionalization of Peptides Employing Metallaphotoredox Catalysis

Access to phosphotyrosine (pTyr) mimetics requires multistep syntheses, and therefore late stage incorporation of these mimetics into peptides is not feasible. Here, we develop and employ metallaphotoredox catalysis using 4-halogenated phenylalanine to afford a variety of protected pTyr mimetics in...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 11; pp. 4244 - 4249
Main Authors Chen, Hao, Mao, Runyu, Brzozowski, Martin, Nguyen, Nghi H, Sleebs, Brad E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.06.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HALIDES
DOMAIN
DESIGN
ARYL
AMINOCARBONYLATION
BROMIDES
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Summary:Access to phosphotyrosine (pTyr) mimetics requires multistep syntheses, and therefore late stage incorporation of these mimetics into peptides is not feasible. Here, we develop and employ metallaphotoredox catalysis using 4-halogenated phenylalanine to afford a variety of protected pTyr mimetics in one step. This methodology was shown to be tolerant of common protecting groups and applicable to the late stage pTyr mimetic modification of protected and unprotected peptides, and peptides of biological relevance.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01200