Telluromethionine

Telluromethionine
Names
	IUPAC name (2S)-2-amino-4-methyltellanylbutanoic acid
	Other names TeMet
Identifiers
3D model (JSmol)	L: Interactive image;
ChemSpider	L: 9033023 ; D/L: 9911402 ;
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 ;
	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). (what is ?) 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

^ ^a ^b 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.
^ 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.
^ 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.
^ 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.

[:0-1] 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.

[Moroder_Musiol_2019_p.-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.

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