title: Synthesis of a selenocysteine-containing peptide by native chemical ligation.
abstract: [reaction in text] A new method for the synthesis of selenocysteine derivatives and selenocysteine-containing peptides is described. Fmoc-Se-p-methoxybenzylselenocysteine (1) was prepared and used for solid-phase synthesis of peptides with an N-terminal unprotected selenocysteine. Subsequent native chemical ligation with a peptide thioester provided a 17-mer that corresponds to the C-terminus of ribonucleotide reductase with selenocysteine in place of cysteine.
authors.affiliation: Department of Chemistry, University of Illinois at Urbana-Champaign, 600 S. Mathews Ave., Urbana, Illinois 61801, USA.
authors.forename: M D
authors.initials: MD
authors.lastname: Gieselman
authors.forename: L
authors.initials: L
authors.lastname: Xie
authors.forename: W A
authors.initials: WA
authors.lastname: van Der Donk
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D012264:Ribonucleotide Reductases / Q000737:chemistry; D017279:Selenocysteine / Q000138:chemical synthesis* / Q000737:chemistry; D020539:Sequence Analysis, Protein; D017386:Sequence Homology, Amino Acid; D013329:Structure-Activity Relationship
chemical_list: D010455:Peptides; D017279:Selenocysteine; D012264:Ribonucleotide Reductases