Biocytin

Biocytin is a chemical compound that is an amide formed from the vitamin biotin and the amino acid L-lysine. As an intermediate in the metabolism of biotin, biocytin occurs naturally in blood serum and urine.

Biocytin
Names
IUPAC name
N6-{5-[(3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}-L-lysine
Systematic IUPAC name
(2S)-2-Amino-6-{5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamido}hexanoic acid
Other names
Biotinyl-L-lysine; Nε-(+)-Biotinyl-L-lysine
Identifiers
3D model (JSmol)
Abbreviations Bct
ChEBI
ChemSpider
UNII
  • InChI=1S/C16H28N4O4S/c17-10(15(22)23)5-3-4-8-18-13(21)7-2-1-6-12-14-11(9-25-12)19-16(24)20-14/h10-12,14H,1-9,17H2,(H,18,21)(H,22,23)(H2,19,20,24)/t10-,11-,12-,14-/m0/s1 checkY
    Key: BAQMYDQNMFBZNA-MNXVOIDGSA-N checkY
  • InChI=1/C16H28N4O4S/c17-10(15(22)23)5-3-4-8-18-13(21)7-2-1-6-12-14-11(9-25-12)19-16(24)20-14/h10-12,14H,1-9,17H2,(H,18,21)(H,22,23)(H2,19,20,24)/t10-,11-,12-,14-/m0/s1
    Key: BAQMYDQNMFBZNA-MNXVOIDGBH
  • O=C1N[C@@H]2[C@@H](SC[C@@H]2N1)CCCCC(=O)NCCCC[C@@H](C(=O)O)N
Properties
C16H28N4O4S
Molar mass 372.48 g·mol−1
Melting point ~245 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The enzyme biotinidase cleaves biocytin and makes biotin available to be reused by other enzymes. Because biocytin is the natural substrate of the enzyme biotinidase, biocytin can be used to measure the biotinidase activity and therefore diagnose biotinidase deficiency.

Biocytin is also used in scientific research as a histological stain for nerve cells.[1]

References
  1. Mishra, Anurag; Dhingra, Kirti; Schüz, Almut; Logothetis, Nikos K.; Canals, Santiago (2010). "Improved Neuronal Tract Tracing with Stable Biocytin-Derived Neuroimaging Agents". ACS Chemical Neuroscience. 1 (2): 129–38. doi:10.1021/cn900010d. PMC 3368650. PMID 22778821.
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