Facile degradative lactonization of Gln-Arg and Gln-Phe hydroxyethylene dipeptide derivatives.
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.
Haug
B E
BE
School of Pharmacy and Department of Chemistry, University of Wisconsin-Madison, USA.
Brewer
M
M
Rich
D H
DH
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*
D004151:Dipeptides; D005030:Ethylenes; D007783:Lactones; D005973:Glutamine; D010649:Phenylalanine; C067254:hydroxyethylene; D001120:Arginine