title: Complex polyfluoride additives in Fmoc-amino acid fluoride coupling processes. Enhanced reactivity and avoidance of stereomutation.
abstract: [reaction: see text] Isolated Fmoc amino acid fluorides have previously been shown to be among the most efficient reagents for peptide bond formation. Now, it has been found that anionic, polyhydrogen fluoride additives are capable of diverting many of the classical peptide coupling processes to acid fluoride couplings. Examples include the use of N-HBTU or N-HATU and the carbodiimide technique. As HF-containing species, these additives provide a more suitable medium for the coupling of systems that are sensitive to loss of configuration at the reactive carboxyl function.
authors.affiliation: Department of Chemistry, University of Massachusetts, Amherst, Massachusetts 01003, USA.
authors.forename: Louis A
authors.initials: LA
authors.lastname: Carpino
authors.forename: Dumitru
authors.initials: D
authors.lastname: Ionescu
authors.forename: Ayman
authors.initials: A
authors.lastname: El-Faham
authors.forename: Michael
authors.initials: M
authors.lastname: Beyermann
authors.forename: Peter
authors.initials: P
authors.lastname: Henklein
authors.forename: Christiane
authors.initials: C
authors.lastname: Hanay
authors.forename: Holger
authors.initials: H
authors.lastname: Wenschuh
authors.forename: Michael
authors.initials: M
authors.lastname: Bienert
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides; D005459:Fluorides