title: Menthols as Chiral Auxiliaries for Asymmetric Cycloadditive Oligomerization: Syntheses and Studies of β-Proline Hexamers.
abstract: 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.
authors.affiliation: 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.
authors.forename: Konstantin V
authors.initials: KV
authors.lastname: Kudryavtsev
authors.affiliation: Department of Chemistry, M.V. Lomonosov Moscow State University , Leninskie Gory 1/3, Moscow 119991, Russian Federation.
authors.forename: Polina M
authors.initials: PM
authors.lastname: Ivantcova
authors.affiliation: Institute of Organic Chemistry, Karlsruhe Institute of Technology , Fritz-Haber-Weg 6, Karlsruhe 76131, Germany.
authors.forename: Claudia
authors.initials: C
authors.lastname: Muhle-Goll
authors.affiliation: Institute of General and Inorganic Chemistry, Russian Academy of Sciences , Leninskii prosp. 31, Moscow 119991, Russian Federation.
authors.forename: Andrei V
authors.initials: AV
authors.lastname: Churakov
authors.affiliation: Department of Chemistry, M.V. Lomonosov Moscow State University , Leninskie Gory 1/3, Moscow 119991, Russian Federation.
authors.forename: Mikhail N
authors.initials: MN
authors.lastname: Sokolov
authors.affiliation: A.N. Belozersky Institute of Physico-Chemical Biology, M.V. Lomonosov Moscow State University , Leninskie Gory 1/40, Moscow 119991, Russian Federation.
authors.forename: Artem V
authors.initials: AV
authors.lastname: Dyuba
authors.affiliation: A.N. Belozersky Institute of Physico-Chemical Biology, M.V. Lomonosov Moscow State University , Leninskie Gory 1/40, Moscow 119991, Russian Federation.
authors.forename: Alexander M
authors.initials: AM
authors.lastname: Arutyunyan
authors.affiliation: Department of Chemistry, University of Durham , South Road, Durham DH1 3LE, U.K.
authors.forename: Judith A K
authors.initials: JA
authors.lastname: Howard
authors.affiliation: School of Pharmacy, National Taiwan University , Linsen S. Rd. 33, Taipei 100, Taiwan.
authors.forename: Chia-Chun
authors.initials: CC
authors.lastname: Yu
authors.affiliation: School of Pharmacy, National Taiwan University , Linsen S. Rd. 33, Taipei 100, Taiwan.
authors.forename: Jih-Hwa
authors.initials: JH
authors.lastname: Guh
authors.affiliation: 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.
authors.forename: Nikolay S
authors.initials: NS
authors.lastname: Zefirov
authors.affiliation: Institute of Organic Chemistry, Karlsruhe Institute of Technology , Fritz-Haber-Weg 6, Karlsruhe 76131, Germany.|Institute of Toxicology and Genetics, Karlsruhe Institute of Technology , Hermann-von-Helmholtz-Platz 1, Eggenstein-Leopoldshafen 76344, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Bräse
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001391:Azo Compounds / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008297:Male; D008610:Menthol / Q000737:chemistry*; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D017433:Protein Structure, Secondary; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D001391:Azo Compounds; D013882:Thiosemicarbazones; C512188:azomethine; D008610:Menthol; D011392:Proline; C072401:beta-proline