Thiol-disulfide exchange yields multivalent dendrimers of melamine.
[reaction: see text] Thiol-disulfide exchange can be used to prepare multivalent conjugates of a small molecule or octapeptide displayed on dendrimers based on melamine. Exchange of four or eight thiopyridyl groups by captopril occurs at room temperature in methanol almost quantitatively. Exchange using the peptide requires higher temperatures and guanidinium chloride in DMF. While exchange on the tetravalent scaffold with four peptides is almost quantitative, sterics retard formation of the octavalent conjugate: the hexavalent conjugate forms readily.
Umali
Alona P
AP
Department of Chemistry, Texas A&M University, College Station, Texas 77843-3255, USA.
Simanek
Eric E
EE
D040761:Biomimetic Materials / Q000737:chemistry; D002216:Captopril / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D008958:Models, Molecular; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D009842:Oligopeptides / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013696:Temperature; D014227:Triazines / Q000737:chemistry*
D004220:Disulfides; D009842:Oligopeptides; D013438:Sulfhydryl Compounds; D014227:Triazines; D002216:Captopril; C011907:melamine; D000432:Methanol