Selenocystine - Misplaced Pages

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/s1Key: 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/s1Key: JULROCUWKLNBSN-QWWZWVQMSA-N
SMILES L: C((C(=O)O)N)C(C(=O)O)N DL: C(C(C(=O)O)N)CC(C(=O)O)N D: C((C(=O)O)N)C(C(=O)O)N
Properties
Chemical formula	C₆H₁₂N₂O₄Se₂
Molar mass	334.114 g·mol
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 , 100 kPa). Infobox references

Chemical compound

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. Because selenocysteine is not easily isolated or handled, it is often generated by reduction of selenocystine in situ. The selenium–selenium bond length is 2.321 Å, which is 14% longer than the disulfide bond in cystine at 2.040 Å.

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.

Encoded (proteinogenic) amino acids

General topics

By properties

Aliphatic	Branched-chain amino acids (Valine Isoleucine Leucine) Methionine Alanine Proline Glycine
Aromatic	Histidine Tyrosine Tryptophan Phenylalanine
Polar, uncharged	Asparagine Glutamine Serine Threonine
Positive charge (pK_a)	Lysine (≈10.8) Arginine (≈12.5) Histidine (≈6.1) Pyrrolysine
Negative charge (pK_a)	Aspartic acid (≈3.9) Glutamic acid (≈4.1) Selenocysteine (≈5.4) Cysteine (≈8.3) Tyrosine (≈10.1)

Amino acids types: Encoded (proteins)
Essential
Non-proteinogenic
Ketogenic
Glucogenic
Secondary amino
Imino acids
D-amino acids
Dehydroamino acids

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