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Org Lett. 2015 Dec 18;17(24):6178-81. doi: 10.1021/acs.orglett.5b03154. Epub 2015 Dec 1.

Menthols as Chiral Auxiliaries for Asymmetric Cycloadditive Oligomerization: Syntheses and Studies of β-Proline Hexamers.

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Department of Chemistry, M.V. Lomonosov Moscow State University , Leninskie Gory 1/3, Moscow 119991, Russian Federation.
Institute of Physiologically Active Compounds, Russian Academy of Sciences , Chernogolovka, Moscow Region 142432, Russian Federation.
Institute of Organic Chemistry, Karlsruhe Institute of Technology , Fritz-Haber-Weg 6, Karlsruhe 76131, Germany.
Institute of General and Inorganic Chemistry, Russian Academy of Sciences , Leninskii prosp. 31, Moscow 119991, Russian Federation.
A.N. Belozersky Institute of Physico-Chemical Biology, M.V. Lomonosov Moscow State University , Leninskie Gory 1/40, Moscow 119991, Russian Federation.
Department of Chemistry, University of Durham , South Road, Durham DH1 3LE, U.K.
School of Pharmacy, National Taiwan University , Linsen S. Rd. 33, Taipei 100, Taiwan.
Institute of Toxicology and Genetics, Karlsruhe Institute of Technology , Hermann-von-Helmholtz-Platz 1, Eggenstein-Leopoldshafen 76344, Germany.


To produce a novel class of structurally ordered poly-β-prolines, an emergent method for synthesizing chiral β-peptide molecular frameworks was developed based on 1,3-dipolar cycloaddition chemistry of azomethine ylides. Functionalized short β-peptides with up to six monomeric residues were efficiently synthesized in homochiral forms using a cycloadditive oligomerization approach. X-ray, NMR, and CD structural analyses of the novel β-peptides revealed secondary structure features that were generated primarily by Z/E-β-peptide bond isomerism. Anticancer in cellulo activity of the new β-peptides toward hormone-refractory prostate cancer cells was observed and was dependent on the absolute configuration of the stereogenic centers and the chain length of the β-proline oligomers.

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