title: Synthesis of modular dipeptide mimetics on the basis of diazabicycloalkanes and derivatives thereof with sulphur containing side chains.
abstract: We present the synthesis of new modular dipeptide mimetics based on diazabicycloalkane backbones. These diazabicycloalkanes are ligands for the prostate specific membrane antigen (PSMA), a well known tumor marker. Our previously described synthetic route to enantiomerically pure diazabicycloalkanes is extended to yield polyfunctional diazabicycloalkanes with a modular character using a new ring closing methodology. This, finally, allows us to attach linker moieties to different positions of the diazabicycloalkane scaffold providing conjugation sites to other functional molecules such as markers or cytostatic compounds. Furthermore, successful synthesis of sulphur-containing dipeptide analogues as for example CysX(AA)- or HCysX(AA)-mimetics on the basis of diazabicycloalkanes is described.
authors.affiliation: Institut für Organische Chemie, Universität Hamburg, Hamburg, Germany.
authors.forename: D C
authors.initials: DC
authors.lastname: Grohs
authors.forename: W
authors.initials: W
authors.lastname: Maison
mesh_terms: D001372:Aza Compounds / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004151:Dipeptides / Q000138:chemical synthesis*; D008024:Ligands; D017430:Prostate-Specific Antigen / Q000378:metabolism
chemical_list: D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D004151:Dipeptides; D008024:Ligands; D017430:Prostate-Specific Antigen; D003545:Cysteine