title: Enantioselective synthesis of N(alpha)-Fmoc protected (2S,3R)-3-phenylpipecolic acid. A constrained phenylalanine analogue suitably protected for solid-phase peptide synthesis.
abstract: Reported herein is the first enantioselective preparation of (2S,3R)-3-phenylpipecolic acid as a conformationally constrained phenylalanine analogue bearing N(alpha)-protection suitable for solid-phase peptide synthesis. Stereochemistries at both the 2- and 3-positions are derived inductively from a single chiral center provided by the commercially available Evans chiral auxiliary, (4S)-4-benzyl-1,3-oxazolidin-2-one. By constraining phi and chi(1) torsion angles, this novel amino acid analogue can serve as a useful tool for the induction of defined geometry in phenylalanine-containing peptides.
authors.affiliation: Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Bldg. 376, Boyles Street, NCI-Frederick, P.O. Box B, Frederick, Maryland 21702-1201, USA.
authors.forename: Ding-Guo
authors.initials: DG
authors.lastname: Liu
authors.forename: Yang
authors.initials: Y
authors.lastname: Gao
authors.forename: Xiangzhu
authors.initials: X
authors.lastname: Wang
authors.forename: James A
authors.initials: JA
authors.lastname: Kelley
authors.forename: Terrence R
authors.initials: TR
authors.lastname: Burke
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C452279:3-phenylpipecolic acid; D002264:Carboxylic Acids; D005449:Fluorenes; D010080:Oxazoles; D010455:Peptides; D010875:Pipecolic Acids; C064210:oxazolidine; D010649:Phenylalanine