Synthesis of a tripeptide derivative containing the Phe-Arg hydroxyethylene dipeptide isostere.
The protected hydroxyethylene dipeptide isostere of Phe-Arg and the tripeptide derivative 1 were synthesized as components of potential peptidase inhibitors. Key to the success of these syntheses is selective rhodium-catalyzed hydroboration in the presence of a readily reduced lactone. A convenient one-pot conversion of azides to diprotected guanidines was developed on the basis of the Staudinger reaction.
Brewer
M
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Department of Chemistry and School of Pharmacy, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
Rich
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D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D005030:Ethylenes / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004151:Dipeptides; D005030:Ethylenes; D007202:Indicators and Reagents; D009842:Oligopeptides; C048251:phenylalanylarginine; C067254:hydroxyethylene