Tellurocysteine (in some publications referred to as Te-Cys) is an amino acid analogous to

serine Serine (symbol Ser or S) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated − form under biological conditions), a carboxyl group (which is in the deprotonated − form un ...

cysteine Cysteine (symbol Cys or C; ) is a semiessential proteinogenic amino acid with the formula . The thiol side chain in cysteine often participates in enzymatic reactions as a nucleophile. When present as a deprotonated catalytic residue, sometime ...

and

selenocysteine Selenocysteine (symbol Sec or U, in older publications also as Se-Cys) is the 21st proteinogenic amino acid. Selenoproteins contain selenocysteine residues. Selenocysteine is an analogue of the more common cysteine with selenium in place of the s ...

with

tellurium Tellurium is a chemical element with the symbol Te and atomic number 52. It is a brittle, mildly toxic, rare, silver-white metalloid. Tellurium is chemically related to selenium and sulfur, all three of which are chalcogens. It is occasionally fou ...

in place of

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...

sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...

selenium Selenium is a chemical element with the symbol Se and atomic number 34. It is a nonmetal (more rarely considered a metalloid) with properties that are intermediate between the elements above and below in the periodic table, sulfur and tellurium, ...

in its side chain. It is not naturally found in organisms.

Properties

Perhaps due to its low bond energy with carbon (200 kJ/mol compared to 234 kJ/mol for selenium, or 272 kJ/mol for sulfur), tellurocysteine is not present in any known natural organisms and is hence relatively understudied in comparison to selenocysteine. Despite so, certain organisms such as fungi ''

Aspergillus fumigatus ''Aspergillus fumigatus'' is a species of fungus in the genus ''Aspergillus'', and is one of the most common ''Aspergillus'' species to cause disease in individuals with an immunodeficiency. ''Aspergillus fumigatus'', a saprotroph widespread in ...

'' is capable of incorporating tellurocysteine and telluromethionine into amino acids and proteins when exposed to a sulfur-free environment. It has been observed that when incorporated into glutathione transferase, tellurocysteine efficiently inhibited

aminoacylation Aminoacylation is the process of adding an aminoacyl group to a compound. See also * Acylation * tRNA aminoacylation * Transfer RNA-like structures References Organic reactions {{Reaction-stub ...

and increased the efficiency of

glutathione peroxidase Glutathione peroxidase (GPx) () is the general name of an enzyme family with peroxidase activity whose main biological role is to protect the organism from oxidative damage. The biochemical function of glutathione peroxidase is to reduce lipid h ...

Synthesis

L-Tellurocysteine has been prepared from elemental

by first reacting it with methyl (2''R'')-2- ''tert''-butoxycarbonyl)amino3-iodopropionate in a

tetrahydrofuran Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is ma ...

solvent with presence of

lithium triethylborohydride Lithium triethylborohydride is the organoboron compound with the formula Li Et3 BH. Commonly referred to as LiTEBH or Superhydride, it is a powerful reducing agent used in organometallic and organic chemistry. It is a colorless or white liquid bu ...

, yielding a red oil which is acidified and treated with alkali before a treatment with

citric acid Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in t ...

to set its pH to 4.0, resulting in an orange solid after filtering and drying.

References

{{Reflist Amino acids Organotellurium compounds