Synthesis of a Gln-Phe hydroxy-ethylene dipeptide isostere.
[structure: see text] The protected Gln-Phe hydroxyethylene dipeptide isostere 1 was synthesized as a precursor for preparation of potential inhibitors of Botulinum neurotoxin B metalloprotease. The method allows for the synthesis of additional hydroxyethylene dipeptide isosteres such as 2 with functionalized P1 side chains. The isosteres prepared were coupled with a dipeptide to produce protected pseudotetrapeptide derivatives.
Haug
Bengt Erik
BE
School of Pharmacy, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
Rich
Daniel H
DH
D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D005030:Ethylenes / Q000737:chemistry*; D005973:Glutamine / Q000737:chemistry*; D015394:Molecular Structure; D010649:Phenylalanine / Q000737:chemistry*; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004151:Dipeptides; D005030:Ethylenes; D011480:Protease Inhibitors; D005973:Glutamine; D010649:Phenylalanine; C067254:hydroxyethylene