https://scholars.lib.ntu.edu.tw/handle/123456789/564772
標題: | Menthols as Chiral Auxiliaries for Asymmetric Cycloadditive Oligomerization: Syntheses and Studies of β-Proline Hexamers | 作者: | Kudryavtsev K.V. Ivantcova P.M. Muhle-Goll C. Churakov A.V. Sokolov M.N. Dyuba A.V. Arutyunyan A.M. Howard J.A.K. Yu C.-C. JIH-HWA GUH Zefirov N.S. Br?se S. |
公開日期: | 2015 | 卷: | 17 | 期: | 24 | 起(迄)頁: | 6178-6181 | 來源出版物: | Organic Letters | 摘要: | 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. ? 2015 American Chemical Society. |
URI: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-84952683177&doi=10.1021%2facs.orglett.5b03154&partnerID=40&md5=94faea4062a5ec3030959fbd537040d3 https://scholars.lib.ntu.edu.tw/handle/123456789/564772 |
ISSN: | 15237060 | DOI: | 10.1021/acs.orglett.5b03154 | SDG/關鍵字: | antineoplastic agent; azo compound; azomethine; beta-proline; menthol; proline; thiosemicarbazone derivative; analogs and derivatives; catalysis; chemical structure; chemistry; cycloaddition; drug screening; human; male; protein secondary structure; stereoisomerism; synthesis; Antineoplastic Agents; Azo Compounds; Catalysis; Cycloaddition Reaction; Drug Screening Assays, Antitumor; Humans; Male; Menthol; Molecular Structure; Proline; Protein Structure, Secondary; Stereoisomerism; Thiosemicarbazones |
顯示於: | 藥學系 |
在 IR 系統中的文件,除了特別指名其著作權條款之外,均受到著作權保護,並且保留所有的權利。