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Post-Assembly Modification of Head-to-Tail Cyclic Peptides by Methionine-Directed β-C(sp 3 )-H Arylation.
- Source :
-
Organic letters [Org Lett] 2022 Aug 12; Vol. 24 (31), pp. 5767-5771. Date of Electronic Publication: 2022 Aug 02. - Publication Year :
- 2022
-
Abstract
- Peptide modification by C(sp <superscript>3</superscript> )-H functionalization of internal residues remains a major challenge due to the inhibitory effect of peptide bonds. In this work, we developed a methionine-directed β-C(sp <superscript>3</superscript> )-H arylation method for internal alanine functionalization. By tuning the σ <subscript>C-C</subscript> bond rotation of internal Ala through head-to-tail cyclization, we overcame the inhibitory effect and functionalized a wide range of head-to-tail cyclic peptides with aryl iodides with excellent position selectivity.
- Subjects :
- Catalysis
Cyclization
Methionine
Palladium chemistry
Peptides, Cyclic
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 24
- Issue :
- 31
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 35916500
- Full Text :
- https://doi.org/10.1021/acs.orglett.2c02253