title: Facile production of mono-substituted urea side chains in solid phase peptide synthesis.
abstract: A method is reported for the straightforward generation of urea-containing peptides during Boc solid phase peptide synthesis. Primary amine side chains are converted to mono-alkyl ureas in two steps via an intermediate p-nitrophenyl carbamate. Use of p-methoxybenzyl amine as an ammonia equivalent affords mono-alkyl final products from standard resin cleavage methods, without the need for additional steps. The reaction is highly efficient and applicable to variable length side chains and peptides.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Maria L
authors.initials: ML
authors.lastname: Diss
authors.forename: Alan J
authors.initials: AJ
authors.lastname: Kennan
mesh_terms: D000595:Amino Acid Sequence; D002219:Carbamates; D002851:Chromatography, High Pressure Liquid; D008969:Molecular Sequence Data; D010455:Peptides / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D012996:Solutions; D014508:Urea / Q000737:chemistry*
chemical_list: D002219:Carbamates; D010455:Peptides; D012996:Solutions; D014508:Urea