title: Dicyclopropylmethyl peptide backbone protectant.
abstract: The N-dicyclopropylmethyl (Dcpm) residue, introduced into amino acids via reaction of dicyclopropylmethanimine hydrochloride with an amino acid ester followed by sodium cyanoborohydride or triacetoxyborohydride reduction, can be used as an amide bond protectant for peptide synthesis. Examples which demonstrate the amelioration of aggregation effects include syntheses of the alanine decapeptide and the prion peptide (106-126). Avoidance of cyclization to the aminosuccinimide followed substitution of Fmoc-(Dcpm)Gly-OH for Fmoc-Gly-OH in the assembly of sequences containing the sensitive Asp-Gly unit.
authors.affiliation: Department of Chemistry, University of Massachusetts, Amherst, Massachusetts 01003, USA. carpino@chem.umass.edu
authors.forename: Louis A
authors.initials: LA
authors.lastname: Carpino
authors.forename: Khaled
authors.initials: K
authors.lastname: Nasr
authors.forename: Adel Ali
authors.initials: AA
authors.lastname: Abdel-Maksoud
authors.forename: Ayman
authors.initials: A
authors.lastname: El-Faham
authors.forename: Dumitru
authors.initials: D
authors.lastname: Ionescu
authors.forename: Peter
authors.initials: P
authors.lastname: Henklein
authors.forename: Holger
authors.initials: H
authors.lastname: Wenschuh
authors.forename: Michael
authors.initials: M
authors.lastname: Beyermann
authors.forename: Eberhard
authors.initials: E
authors.lastname: Krause
authors.forename: Michael
authors.initials: M
authors.lastname: Bienert
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000596:Amino Acids; D003521:Cyclopropanes; D004151:Dipeptides; D009842:Oligopeptides; C017033:aspartylglycine