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
Show more names
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
- Formal charge
- 0
- Complexity
- 491
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)
- form
- Solid
- pka
- 2.53 · 2.53±0.24(Predicted)
- color
- White to Off-White
- Appearance
- White to off-white powder
- optical activity
- 20 · [α]20/D +53°, c = 1.05% in 0.1 M NaOH(lit.)
- Water Solubility
- Soluble in water (50 mM)
- Merck
- 13 · 13,1227
- BRN
- 97197 · 97197
- InChIKey
- BAQMYDQNMFBZNA-MNXVOIDGSA-N
- SMILES
- C(O)(=O)[C@H](CCCCNC(=O)CCCC[C@H]1[C@@]2([H])NC(=O)N[C@@]2([H])CS1)N
- FDA UNII
- 6 D6147J22 · G6D6147J22
- UNSPSC Code
- 12352209 · 12352209
- NACRES
- 26 · NA.26
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- WGK Germany
- 3 · 3
- HS Code
- 29362900 · 29362900
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29362900
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
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
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
Compound notes
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