Advances in the Synthesis of Bioactive Unnatural Amino Acids and Peptides

R. Saladino, G. Botta, M. Crucianelli

Abstract

The key role of proteins and amino acids in the structure and function of living matter has stimulated extensive studies. Modified amino acids with enhanced biological activity, proteolitic stability and bioavailability are of increasing interest in protein design and engineering as drug candidates. In the last few years, several efforts have been devoted to the synthesis of amino acids having unusual side chains and unnatural chirality, commonly referred to as “nonproteinogenic” or “unnatural” amino acids, even though some of them can be isolated from natural sources. In this review we describe recent advances in the amino acid side-chain transformations and backbone modifications by oxidative and fluorination procedures.

Keywords: Unnatural amino acids, peptidomimetics, biological activity, synthesis, structural preperties, fluorination, cycloaddition reactions, N-benzyloxycarbonyl, α-ketoamide, diisobutylaluminum hydride, sulfoxide

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Mini-Reviews in Medicinal Chemistry

Title:Advances in the Synthesis of Bioactive Unnatural Amino Acids and Peptides

Volume: 12 Issue: 4

Author(s): R. Saladino, G. Botta, M. Crucianelli

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Abstract: The key role of proteins and amino acids in the structure and function of living matter has stimulated extensive studies. Modified amino acids with enhanced biological activity, proteolitic stability and bioavailability are of increasing interest in protein design and engineering as drug candidates. In the last few years, several efforts have been devoted to the synthesis of amino acids having unusual side chains and unnatural chirality, commonly referred to as “nonproteinogenic” or “unnatural” amino acids, even though some of them can be isolated from natural sources. In this review we describe recent advances in the amino acid side-chain transformations and backbone modifications by oxidative and fluorination procedures.

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R. Saladino, G. Botta, M. Crucianelli , Advances in the Synthesis of Bioactive Unnatural Amino Acids and Peptides, Mini-Reviews in Medicinal Chemistry 2012; 12 (4) . https://dx.doi.org/10.2174/138955712799829276

DOI https://dx.doi.org/10.2174/138955712799829276	Print ISSN 1389-5575
Publisher Name Bentham Science Publisher	Online ISSN 1875-5607

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