title: Facile degradative lactonization of Gln-Arg and Gln-Phe hydroxyethylene dipeptide derivatives.
abstract: We have found that hydroxyrthylene (HE) dipeptide analogs of Gln-Arg and Gln-Phe are usually susceptible to acid catalyzed lactonization. The synthesis of substrate-based transition state analog inhibitors of botulinum neurotoxin metalloprotease inhibitors that contain the Gln-Arg or the Gln-Phe HE units is complicated by this facile degradative lactonization.
authors.affiliation: School of Pharmacy and Department of Chemistry, University of Wisconsin-Madison, USA.
authors.forename: B E
authors.initials: BE
authors.lastname: Haug
authors.forename: M
authors.initials: M
authors.lastname: Brewer
authors.forename: D H
authors.initials: DH
authors.lastname: Rich
mesh_terms: D001120:Arginine / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry*; D005973:Glutamine / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010649:Phenylalanine / Q000737:chemistry*
chemical_list: D004151:Dipeptides; D005030:Ethylenes; D007783:Lactones; D005973:Glutamine; D010649:Phenylalanine; C067254:hydroxyethylene; D001120:Arginine