title: New reagents, reactions, and peptidomimetics for drug design.
abstract: It has been a major focus in our laboratories to prepare novel reagents and peptidomimetic structures for drug design. We have designed and prepared novel guanidinylation reagents that can be employed in solution or as solid phase reagents. We and others have utilized the reagent 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) for amide bond formation to couple sterically hindered structures. These couplings proceed with remarkably strong resistance to racemization. In the area of peptidomimetics, we have incorporated novel building blocks to create biologically active compounds. These building blocks include thioether and alkylamine bridges, beta-methylated, and beta,beta-dimethylated amino acid residues. These mimetic structures have been incorporated into specific target molecules such as opioids to obtain cyclic peptidomimetics with potent and selective biological activity.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343, USA. mgoodman@ucsd.edu
authors.forename: M
authors.initials: M
authors.lastname: Goodman
authors.forename: C
authors.initials: C
authors.lastname: Zapf
authors.forename: Y
authors.initials: Y
authors.lastname: Rew
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D015195:Drug Design; D004745:Enkephalins / Q000737:chemistry; D019791:Guanidine / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D008956:Models, Chemical; D010755:Organophosphates / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D013440:Sulfides; D014227:Triazines / Q000737:chemistry*
chemical_list: C410327:3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; D000588:Amines; D000596:Amino Acids; D004745:Enkephalins; D007202:Indicators and Reagents; D010755:Organophosphates; D010455:Peptides; D013440:Sulfides; D014227:Triazines; C001520:lanthionine; D019791:Guanidine; D000409:Alanine