Transfer of the Chiral Information of Natural Amino Acids in Biomimetic Organic Syntheses

Károly Micskei, Csongor Hajdu, Tamás Patonay, Claudia Zucchi, Luciano Caglioti, Gyula Pályi

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Abstract

In their complexes, natural amino acids are typically coordinated through the α-amino and carboxyl (ate) groups as bidentate ligands forming stable five-membered rings. The stability, structure, reactivity, and solubility of these complexes are influenced in a broad range by the structure of the α-substituent. Several classifications based on the structure of these side chains have been done, which are widely used in biochemistry to interpret (or predict) the behavior of amino acids, as well as their oligo- and polycondensates. One of the most important features is the polarity of the side chain. The following natural amino acids can be regarded typically apolar: Ala, Val, Leu, He, Pro, Phe, Tyr, Trp, Cys, and Met. These representatives are characterized by low solubility and micelle formation in water. The members of other group (Lys, Arg, His, Asp, Glu, Asn, and Gin) bear polar, mostly dissociable groups in their side chain, which assures a good solvation in water and higher solubility. Although the majority of the natural amino acids possess groups with typical ligand properties in the side chain, in aqueous solution these are only weakly or not coordinated. Only three natural amino acids can be regarded as tridentate (His, Asp, and Cys). All natural amino acids, with the exception of Gly, contain at least one stereogenic center (the α-carbon atom) and belong to the L-series in majority of cases.

Original languageEnglish
Title of host publicationProgress in Biological Chirality
PublisherElsevier Inc.
Pages221-235
Number of pages15
ISBN (Print)9780080443966
DOIs
Publication statusPublished - Sep 2004

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ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

Micskei, K., Hajdu, C., Patonay, T., Zucchi, C., Caglioti, L., & Pályi, G. (2004). Transfer of the Chiral Information of Natural Amino Acids in Biomimetic Organic Syntheses. In Progress in Biological Chirality (pp. 221-235). Elsevier Inc.. https://doi.org/10.1016/B978-008044396-6/50020-4