期刊
CHEMBIOCHEM
卷 22, 期 2, 页码 330-335出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.202000424
关键词
ghrelin; metadynamics; NMR spectroscopy; peptide; tryptophan
资金
- Helmholtz-Institut for Metabolismus-, Adipositas- und Gefassforschung [HIMAG-111]
A generalized synthetic strategy is proposed for asymmetric beta-indoylated amino acids by 8-aminoquinoline (8AQ)-directed C(sp(3))-H functionalization. The peptides with (indol-3-yl)-3-phenylalanine at position 2 have shown a wide range of activities as ghrelin receptor inverse agonists, demonstrating the potential for systematic variation of indole group position in bioactive peptides.
A generalized synthetic strategy is proposed here for the synthesis of asymmetric beta-indoylated amino acids by 8-aminoquinoline (8AQ)-directed C(sp(3))-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 beta-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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