Selenocystine

Selenocystine
Identifiers
3D model (JSmol)
1969559
ChEBI
ChemSpider
ECHA InfoCard 100.130.419 Edit this at Wikidata
EC Number
  • L: 608-382-6
  • DL: 636-685-3
KEGG
UNII
  • 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
C6H12N2O4Se2
Molar mass 334.114 g·mol−1
Appearance white solid
Melting point 222 °C (432 °F; 495 K)
Hazards
GHS labelling:[1]
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H331, H373, H410
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).

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. Bibcode:2015AcCrE..71..726G. doi:10.1107/S205698901501021X. PMC 4459342. PMID 26090162.