title: Synthesis and reactions of fluorous carbobenzyloxy (FCbz) derivatives of alpha-amino acids.
abstract: Fluorous carbobenzyloxy ((F)Cbz) reagents RfCH(2)CH(2)C(6)H(4)CH(2)OC(O)OSu (where Su is succinimidoyl and Rf is C(6)F(13) and C(8)F(17)) have been used to make (F)Cbz derivatives of 18 of the 20 natural amino acids. The potential utility of this new family of reagents in both standard fluorous synthesis with spe separation and fluorous quasiracemic synthesis is illustrated with representative reactions of the (F)Cbz-Phe derivatives.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA. curran@pitt.edu
authors.forename: Dennis P
authors.initials: DP
authors.lastname: Curran
authors.forename: Muriel
authors.initials: M
authors.lastname: Amatore
authors.forename: David
authors.initials: D
authors.lastname: Guthrie
authors.forename: Matthew
authors.initials: M
authors.lastname: Campbell
authors.forename: Eisan
authors.initials: E
authors.lastname: Go
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Luo
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D005459:Fluorides / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001555:Benzene Derivatives; D007202:Indicators and Reagents; D005459:Fluorides