title: A solid-phase synthetic strategy for labeled peptides: synthesis of a biotinylated derivative of the delta opioid receptor antagonist TIPP (Tyr-Tic-Phe-Phe-OH).
abstract: A general solid-phase synthetic strategy for labeled peptides was developed and used to prepare a biotinylated derivative of the delta opioid receptor antagonist TIPP (Tyr-Tic-Phe-Phe-OH). A monoprotected hydrophilic diamine linker was attached to an aldehyde-containing solid-phase resin by reductive amination, followed by introduction of biotin and peptide synthesis to yield Tyr-Tic-Phe-Phe-Asp-NH(CH(2)CH(2)O)(2)CH(2)CH(2)NH-biotin (2). The high delta receptor affinity and selectivity of 2 demonstrate the applicability of this design approach for labeled peptide derivatives.
authors.affiliation: Department of Pharmaceutical Sciences, School of Pharmacy, University of Maryland, Baltimore, Maryland 21201, USA.
authors.forename: Vivek
authors.initials: V
authors.lastname: Kumar
authors.forename: Jane V
authors.initials: JV
authors.lastname: Aldrich
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000586:Amination; D000595:Amino Acid Sequence; D019921:Biotinylation; D003959:Diamines / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D010084:Oxidation-Reduction; D017465:Receptors, Opioid, delta / Q000037:antagonists & inhibitors* / Q000378:metabolism; D044005:Tetrahydroisoquinolines
chemical_list: D000447:Aldehydes; D003959:Diamines; D009842:Oligopeptides; D017465:Receptors, Opioid, delta; D044005:Tetrahydroisoquinolines; C082263:tyrosyl-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-phenylalanyl-phenylalanine