Menthols as Chiral Auxiliaries for Asymmetric Cycloadditive Oligomerization: Syntheses and Studies of 尾-Proline Hexamers
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- 作者：Konstantin V. Kudryavtsev ; Polina M. Ivantcova ; Claudia Muhle-Goll ; Andrei V. Churakov ; Mikhail N. Sokolov ; Artem V. Dyuba ; Alexander M. Arutyunyan ; Judith A. K. Howard ; Chia-Chun Yu ; Jih-Hwa Guh ; Nikolay S. Zefirov ; Stefan Br盲se
- 刊名：Organic Letters
- 出版年：2015
- 出版时间：December 18, 2015
- 年：2015
- 卷：17
- 期：24
- 页码：6178-6181
- 全文大小：331K
- ISSN：1523-7052
文摘
To produce a novel class of structurally ordered poly-尾-prolines, an emergent method for synthesizing chiral 尾-peptide molecular frameworks was developed based on 1,3-dipolar cycloaddition chemistry of azomethine ylides. Functionalized short 尾-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 尾-peptides revealed secondary structure features that were generated primarily by Z/E-尾-peptide bond isomerism. Anticancer in cellulo activity of the new 尾-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 尾-proline oligomers.