4.5 Review

Recent Advances in the Synthesis of Fluorinated Amino Acids

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 18, 页码 3261-3278

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100032

关键词

Synthetic methods; Asymmetric synthesis; Fluorine; Amino acids

资金

  1. National Natural Science Foundation of China [21072028, 20832008]

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Introduction of fluorine atoms or fluorine-containing groups into amino acids has attracted much attention from bioorganic and medicinal chemists because the resulting fluorinated amino acids have found wide application as potential enzyme inhibitors and antitumor (antibacterial) agents. Additionally, it is well known that replacement of naturally occurring amino acid(s) in some peptide chains with their fluorinated counterparts can significantly increase specific protein-ligand or protein-protein interactions, leading to in-creases in the proteolytic and thermal stabilities of peptide compounds and, as a result, promote their therapeutic properties. This microreview summarizes important advances in the synthesis of fluorinated amino acids since 2005. The contents are simply divided into three groups on the basis of amino acid types: fluorinated alpha-amino acids (F-alpha AAs), fluorinated beta-amino acids (F-beta AAs), and fluorinated cyclic amino acids (F-CAAs).

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