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1-amino-2-phenylcyclopentane-1-carboxylic acid: A conformationally restricted phenylalanine analogue

  1. Author:
    Casanovas, J.
    Jimenez, A. I.
    Cativiela, C.
    Nussinov, R.
    Aleman, C.

  2. Author Address

    Casanovas, Jordi] Univ Lleida, Escola Politecn Super, Dept Quim, E-25001 Lleida, Spain. [Jimenez, Ana I.; Cativiela, Carlos] Univ Zaragoza, CSIC, Dept Quim Organ, Inst Ciencia Mat Aragon, E-50009 Zaragoza, Spain. [Nussinov, Ruth] NCI, Basic Res Program, SAIC Frederick Inc, Ctr Canc Res Nanobiol Program, Frederick, MD 21702 USA. [Nussinov, Ruth] Tel Aviv Univ, Sackler Sch Med, Dept Human Genet, IL-69978 Tel Aviv, Israel. [Aleman, Carlos] Univ Politecn Cataluna, Dept Engn Quim, ETS Engn Ind Barcelona, E-08028 Barcelona, Spain.
    1. Year: 2008
  2. Journal: Journal of Organic Chemistry
    1. 73
    2. 2
    3. Pages: 644-651
  4. Type of Article: Article
  1. Abstract:

    DFT calculations at the B3LYP/6-311G(d,p) level have been used to investigate the intrinsic conformational preferences of 1-amino-2-phenylcyclopentane-1-carboxylic acid (c(5)Phe), a constrained analogue of phenylalanine in which the alpha and beta carbons are included in a cyclopentane ring. Specifically, the N'-acetyl-N'-methylamide derivatives of the cis and trans stereoisomers, where cis and trans refer to the relative position between the amino group and the phenyl ring, have been calculated. Solvent effects have been examined using a self-consistent reaction field (SCRF) method. Results indicate that the conformational space of the cis stereoisomer is much more restricted than that of the trans derivative both in the gas phase and in solution.

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External Sources

  1. PMID: 18081347

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