Selenocystine

Selenocystine
Identifiers
CAS Number	L: 29621-88-3; DL: 2897-21-4; D: 26932-45-6;
3D model (JSmol)	L: Interactive image; DL: Interactive image; D: Interactive image;
Beilstein Reference	1969559
ChEBI	DL: CHEBI:28553;
ChemSpider	L: 179613; DL: 14376;
ECHA InfoCard	100.130.419
EC Number	L: 608-382-6; DL: 636-685-3;
KEGG	L: C05704;
PubChem CID	L: 207306; DL: 15104; D: 33648;
UNII	L: 261B157KR8; DL: 493154PTZ7; D: 36B4M60N9C;
CompTox Dashboard (EPA)	L: DTXSID001044310 ;
	InChI InChI=1S/C6H12N2O4Se2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1 Key: JULROCUWKLNBSN-IMJSIDKUSA-N; DL: InChI=1S/C6H12N2O4Se2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12) Key: JULROCUWKLNBSN-UHFFFAOYSA-N; D: InChI=1S/C6H12N2O4Se2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m1/s1 Key: JULROCUWKLNBSN-QWWZWVQMSA-N;
	SMILES L: C([C@@H](C(=O)O)N)[Se][Se]C[C@@H](C(=O)O)N; DL: C(C(C(=O)O)N)[Se][Se]CC(C(=O)O)N; D: C([C@H](C(=O)O)N)[Se][Se]C[C@H](C(=O)O)N;
Properties
Chemical formula	C6H12N2O4Se2
Molar mass	334.114 g·mol−1
Appearance	white solid
Melting point	222 °C (432 °F; 495 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H331, H373, H410
Precautionary statements	P260, P261, P264, P270, P271, P273, P301+P316, P304+P340, P316, P319, P321, P330, P391, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Selenocystine is the amino acid with the formula (HO₂CCH(NH₂)CH₂Se)₂. It is the oxidized derivative of the canonical amino acid selenocysteine (HO₂CCH(NH₂)CH₂SeH). The compound can also be prepared synthetically from serine.^[2] Because selenocysteine is not easily isolated or handled, it is often generated by reduction of selenocystine in situ.^[3] The selenium–selenium bond length is 2.321 Å, which is 14% longer than the disulfide bond in cystine at 2.040 Å.^[4]

References

^ "L-Selenocystine". pubchem.ncbi.nlm.nih.gov.
^ Muttenthaler, Markus; Alewood, Paul F. (2008). "Selenopeptide chemistry". Journal of Peptide Science. 14 (12): 1223–1239. doi:10.1002/psc.1075. PMID 18951416. S2CID 27755359.
^ Tapiero, H.; Townsend, D.M; Tew, K.D (2003). "The antioxidant role of selenium and seleno-compounds". Biomedicine & Pharmacotherapy. 57 (3–4): 134–144. doi:10.1016/S0753-3322(03)00035-0. PMC 6361120. PMID 12818475.
^ Görbitz, Carl Henrik; Levchenko, Vladimir; Semjonovs, Jevgenijs; Sharif, Mohamed Yusuf (2015). "Crystal structure of seleno-L-cystine dihydrochloride". Acta Crystallogr. E. 71 (Pt 6): 726–729. Bibcode:2015AcCrE..71..726G. doi:10.1107/S205698901501021X. PMC 4459342. PMID 26090162.

[1] "L-Selenocystine". pubchem.ncbi.nlm.nih.gov.

[2] Muttenthaler, Markus; Alewood, Paul F. (2008). "Selenopeptide chemistry". Journal of Peptide Science. 14 (12): 1223–1239. doi:10.1002/psc.1075. PMID 18951416. S2CID 27755359.

[3] Tapiero, H.; Townsend, D.M; Tew, K.D (2003). "The antioxidant role of selenium and seleno-compounds". Biomedicine & Pharmacotherapy. 57 (3–4): 134–144. doi:10.1016/S0753-3322(03)00035-0. PMC 6361120. PMID 12818475.

[4] Görbitz, Carl Henrik; Levchenko, Vladimir; Semjonovs, Jevgenijs; Sharif, Mohamed Yusuf (2015). "Crystal structure of seleno-L-cystine dihydrochloride". Acta Crystallogr. E. 71 (Pt 6): 726–729. Bibcode:2015AcCrE..71..726G. doi:10.1107/S205698901501021X. PMC 4459342. PMID 26090162.

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