Telluromethionine

Telluromethionine

Names
IUPAC name (2S)-2-amino-4-methyltellanylbutanoic acid
Other names TeMet
Identifiers
3D model (JSmol)	L: Interactive image
ChemSpider	L: 9033023  Y D/L: 9911402  Y
PubChem CID	L: 10857732
InChI InChI=1S/C5H11NO2Te/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 Y
SMILES L:C[Te]CCC(C(=O)O)N
Properties
Chemical formula	C 5H 11NO 2Te
Molar mass	244.7 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N (what is  YN ?) Infobox references

Telluromethionine (sometimes shortened to TeMet ^[1] ) is a rare and natural amino acid. ^[2] It is a heavy analog of methionine and selenomethionine containing tellurium. Telluromethionine has been suggested as a probe for structural biochemistry, as it can be incorporated into proteins and used for X-ray crystallography and NMR measurements. ^[3]

In aqueous solutions, telluromethioning oxidizes to a telluroxide, but can be recovered by use of DTT. Telluromethionine is not very stable in wheat germ extract, which impacts its translation rate. In the extract, elemental tellurium seems to form, suggesting a degradation mechanism, but this is not well understood. ^[1] However, enriching proteins with tellurium in auxotrophic E. coli was successfully used to express several recombinant proteins. ^[4]

References

1. Ogra, Yasumitsu; Kitaguchi, Takashi; Suzuki, Noriyuki; Suzuki, Kazuo T. (2008-01-01). "In vitro translation with [34S]-labeled methionine, selenomethionine, and telluromethionine" . Analytical and Bioanalytical Chemistry. 390 (1): 45–51. doi:10.1007/s00216-007-1546-y. ISSN   1618-2650. PMID   17846751.
2. Moroder, Luis; Musiol, Hans-Jürgen (2019-12-19). "Amino acid chalcogen analogues as tools in peptide and protein research". Journal of Peptide Science. 26 (2). Wiley: e3232. doi:10.1002/psc.3232. hdl: 21.11116/0000-0005-A122-E . ISSN   1075-2617. PMID   31856429.
3. Boles, J O; Lebioda, L; Dunlap, R B; Odom, J D (1995-01-01). "Telluromethionine in structural biochemistry". SAAS Bulletin, Biochemistry and Biotechnology. 8: 29–34. ISSN   1052-6781. PMID   7546573.
4. Budisa, Nediljko; Karnbrock, Wilhelm; Steinbacher, Stefan; Humm, Andreas; Prade, Lars; Neuefeind, Torsten; Moroder, Luis; Huber, Robert (1997-07-25). "Bioincorporation of telluromethionine into proteins: a promising new approach for X-ray structure analysis of proteins11Edited by K. Nagai" . Journal of Molecular Biology. 270 (4): 616–623. doi:10.1006/jmbi.1997.1132. ISSN   0022-2836. PMID   9245591.