Synthesis of β‑Thiol Phenylalanine for Applications in One-Pot Ligation–Desulfurization Chemistry

Synthesis of β‑Thiol Phenylalanine for Applications in One-Pot Ligation–Desulfurization Chemistry

The efficient synthesis of a β-thiol phenylalanine derivative is described starting from Garner’s aldehyde. The utility of this amino acid in peptide ligation–desulfurization chemistry is described, including the trifluoroethanethiol (TFET)-promoted one-pot assembly of the 62 residue peptide hormone...

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Veröffentlicht in:Organic letters 2015-05, Vol.17 (9), p.2070-2073
Hauptverfasser: Malins, Lara R, Giltrap, Andrew M, Dowman, Luke J, Payne, Richard J
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Ligation
Molecular Structure
Neoplasm Proteins - chemistry
Peptide Hormones - chemistry
Peptides - chemistry
Phenylalanine - analogs & derivatives
Phenylalanine - chemical synthesis
Phenylalanine - chemistry
Sulfhydryl Compounds - chemical synthesis
Sulfhydryl Compounds - chemistry
Trifluoroethanol - analogs & derivatives
Trifluoroethanol - chemistry
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Zusammenfassung:The efficient synthesis of a β-thiol phenylalanine derivative is described starting from Garner’s aldehyde. The utility of this amino acid in peptide ligation–desulfurization chemistry is described, including the trifluoroethanethiol (TFET)-promoted one-pot assembly of the 62 residue peptide hormone augurin.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00597