Tryptophan Analogues with Fixed Side-Chain Orientation: Expanding the Scope.
Chembiochem
; 22(2): 330-335, 2021 01 15.
Article
em En
| MEDLINE
| ID: mdl-33463878
ABSTRACT
A generalized synthetic strategy is proposed here for the synthesis of asymmetric ß-indoylated amino acids by 8-aminoquinoline (8AQ)-directed C(sp3)-H functionalization of suitably protected precursors. Peptides containing one of the four stereoisomers of (indol-3-yl)-3-phenylalanine at position 2 of the parent peptide KwFwLL-NH2 (w=d-Trp) cover a wide range of activities as ghrelin receptor inverse agonists, among them the most active described until now. This application exemplarily shows how ß-indoylated amino acids can be used for the systematic variation of the position of an indole group in a bioactive peptide.
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MEDLINE
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En
Ano de publicação:
2021
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Article