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 Edit this at Wikidata
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 Edit this at Wikidata
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
  • 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:[1]
Pictograms
 GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
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
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.[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

  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. doi:10.1107/S205698901501021X. PMC 4459342. PMID 26090162.