title: Asymmetric synthesis of vinylogous β-amino acids and their incorporation into mixed backbone oligomers.
abstract: Chiral vinylogous β-amino acids (VBAA) were synthesized using enantioselective Mannich reactions of aldehydes with in situ generated N-carbamoyl imines followed by a Horner-Wadsworth-Emmons reaction. The efficiency with which these units could be incorporated into oligomers with different moieties on the C- and N-terminal sides was established, as was the feasibility of sequencing oligomers containing VBAAs by tandem mass spectrometry. The data show that VBAAs will be useful building blocks for the construction of combinatorial libraries of peptidomimetic compounds.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 130 Scripps Way, Jupiter, FL 33458, USA. kodadek@scripps.edu.
authors.forename: Hao
authors.initials: H
authors.lastname: Wu
authors.forename: Hongchan
authors.initials: H
authors.lastname: An
authors.forename: Shuting Cynthia
authors.initials: SC
authors.lastname: Mo
authors.forename: Thomas
authors.initials: T
authors.lastname: Kodadek
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D007097:Imines / Q000737:chemistry; D058105:Polymerization; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D000596:Amino Acids; D007097:Imines