Synthesis of Selenocysteine and Selenomethionine Derivatives from Sulfur‐Containing Amino Acids

Abstract

Selenium-containing amino acids have attracted increasing interest from view points of the importance as active centers of several selenoenzymes, the biological synthesis, the metabolism, and the use for structure determination of proteins. In this article, our recent progresses in the transformation from sulfur-containing amino acids to selenocysteine (SeCys) and selenomethionine (SeMet) derivatives are reviewed along with the surveys of general organic methodologies for the synthesis of SeCys and SeMet derivatives in the literature. The S-->Se modification (i.e., the chemical atomic mutation) would be a useful approach to peptide synthesis involving selenoamino acid residues.

A study of [Au(ethylenediamine)Cl2]Cl interaction with L-methionine and DL-seleno-methionine by1H and13C NMR spectroscopy

“…Met is an essential α-amino acid classified as nonpolar, and together with L-cysteine, constitute the two sulfur-containing proteinogenic amino acids [10]. It is also one of the most important bio-ligands that affect the efficacy of antitumor complexes.…”

“…Gold complexes have been studied extensively as antiarthritic and anticancer agents during the last four decades [1][2][3][4][5][6][7][8][9][10][11][12][13]. Auranofin and Myocrisin are some examples of gold(I) drugs that have been used for the treatment of rheumatoid arthritis [7,13].…”

Using chemical approaches to study selenoproteins—Focus on thioredoxin reductases

“…For a few years, the derivative Fmoc-Sec(Mob), was available from NovaBiochem for > $2,000 per gram, and as far as this author is aware, the derivative is no longer commercially available. Two recent reviews have been published on methods for making L -selenocystine [32,33], so I will not elaborate further other than to say a common method (used by us) is to make L -selenocystine from elemental selenium and L -β-chloro-alanine. A second major problem is the compatibility of Sec with the various protecting groups that have been used for Cys.…”

The Selenium Supplementation Influences Olive Tree Production and Oil Stability Against Oxidation and Can Alleviate the Water Deficiency Effects

“…Once administrated because of its chemical similarity to sulfur (S) Se is generally taken up by the plant via sulfate transporters and then metabolized via the S assimilation pathway (Sors et al, 2005), which may incorporate this micronutrient into organic forms such as SeCys and SeMet. Recently, interest in seleno-amino acids has increased because they integrate the active centers of several selenoenzymes, which are involved in biological synthesis and plant metabolism, and are used for protein structure determinations (Iwaoka et al, 2008). For example, the study performed by Torres et al (2014) on EVOO obtained from olive groves in Argentina grown on soil containing Se, has shown the presence of seleno-amino acids such as SeMeSeCys and selenocysteine.…”