1-Amino-2-Phenylcyclopentane-1-carboxylic Acid: A Conformationally Restricted Phenylalanine Analogue

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• 作者：Jordi Casanovas ; Ana I. Jim&eacute ; nez ; Carlos Cativiela ; Ruth Nussinov ; Carlos Alemá ; n
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：January 18, 2008
• 年：2008
• 卷：73
• 期：2
• 页码：644 - 651
• 全文大小：268K
• 年卷期：v.73,no.2(January 18, 2008)
• ISSN：1520-6904

文摘

DFT calculations at the B3LYP/6-311G(d,p) level have been used to investigate the intrinsic conformationalpreferences of 1-amino-2-phenylcyclopentane-1-carboxylic acid (c₅Phe), a constrained analogue ofphenylalanine in which the and 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 relativeposition between the amino group and the phenyl ring, have been calculated. Solvent effects have beenexamined using a self-consistent reaction field (SCRF) method. Results indicate that the conformationalspace of the cis stereoisomer is much more restricted than that of the trans derivative both in the gasphase and in solution.