Biocytin

HCID 83814

Basic information

CAS
576-19-2
Standard SMILES
N[C@@H](CCCCNC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)C(=O)O
InChIKey
BAQMYDQNMFBZNA-MNXVOIDGSA-N
Molecular formula
C16H28N4O4S
Average molar mass
372.5 g/mol
Monoisotopic mass
372.18312656

Names & identifiers

Preferred name
Biocytin
IUPAC
(2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-aminohexanoic acid
English name
Biocytin
Molecular formula
C16H28N4O4S
Molecular weight
372.48

Names & synonyms

Biocytin576-19-2Biotinyl-L-lysineepsilon-N-Biotinyl-L-lysineG6D6147J22CHEBI:27870DTXSID30973172(2S)-6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-2-aminohexanoic acid(2S)-6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-2-aminohexanoic acid(2S)-6-(5-((3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-4-yl)pentanoylamino)-2-aminohexanoic acid(2S)-6-(5-((3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-4-yl)pentanoylamino)-2-azaniumylhexanoate(2S)-6-(5-((3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno(3,4-d)imidazolidin-4-yl)pentanamido)-2-aminohexanoic acid
Show more names
d-BiocytinBCTL-BIOCYTINH-LYS(BIOT)-OHH-Lys(biotinyl)BIOCYTIN FREE BASEBiocytin (εL-Lys(biotinyl)-OH
RefChem:119845DTXCID401400629H-Lys(biotinyl)-OHN'-Biotinyl-L-lysineMFCD00077319N6-[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1-oxopentyl]-L-LysineL-Lysine,N6-[5-[(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1-oxopentyl]-C16H28N4O4S

Database identifiers

CAS
576-19-2
PubChem CID
83814
ChEBI
CHEBI:27870
UNII
G6D6147J22
Nikkaji
J9.428E

Properties

Computed structural properties

XLogP
-2.4
Topological polar surface area
159 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
6
Rotatable bonds
11
Heavy atoms
25

Physicochemical properties

Melting point
245 °C · ~245 °C (dec.) (lit.)
alpha
25 · D25 +53° (c = 1.05 in 0.1N NaOH)
Boiling point
748 · 748.0±60.0 °C(Predicted)
Density
1.234 · 1.234
storage temp.
-20 °C · -20°C
solubility
Aqueous Base (Slightly), Water (Slightly, Sonicated)

Safety & regulation

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
hs_code
29362900
Storage Class
11 - Combustible Solids

Chemistry & industry

Applications · 4 items

DescriptionBiocytin is a conjugate of biotin and lysine known formally as ε-N-(d-biotinyl)-L-lysine. The addition of lysine to biotin increases the chain length extending from biotin, allowing the synthesis of medium-chain reagents. It also provides terminal carboxyl and amino groups for derivatization or conjugation to proteins and other molecules. Covalent linking reactions typically involve carbodiimide or NHS-ester crosslinking chemistries. Biocytin is also used as an anterograde, retrograde, or intracellular neuroanatomical tracer that is fixable with aldehyde-based fixatives. For this and other applications, biocytin is detected with avidin or streptavidin probes.

UsesUseful for the synthesis of Biocytin containing peptides to study the mechanism of reactions catalyzed by biotin - containing enzymes

UsesBiocytin can be used as a versatile fluorescent marker for neuroanatomical investigations and for a biotinidase assay.

UsesBiocytin is used as a substrate to study the specificity and kinetics of biotinidase(s), to measure biotinidase deficiency and as a model compound to study various uptake mechanisms of cells and tissues. Biocytin has been used to label neurons, medium spiny neurons and optic nerves.

Suppliers101 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]

Additional notes

DefinitionChEBI: A monocarboxylic acid amide that results from the formal condensation of the carboxylic acid group of biotin with the N6-amino group of L-lysine.

Related reactions

1 records

Compound notes

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