Biocytin supplier | CasNO.576-19-2

Name
Biocytin
EINECS
CAS No. 576-19-2
Article Data12
CAS DataBase
Density 1.234g/cm³
Solubility
Melting Point 241-243 °C
Formula C₁₆H₂₈N₄O₄S
Boiling Point 748 °C at 760 mmHg
Molecular Weight 372.489
Flash Point 406.2 °C
Transport Information
Appearance White Solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms L-Lysine, N~6~-[5-[(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1-oxopentyl]-;N~6~-{5-[(3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}-L-lysine;L-Lysine, N6-(5-(hexahydro-2-oxo-1H-thieno(3,4-d)imidazol-4-yl)-1-oxopentyl)-, (3aS-(3aalpha,4beta,6aalpha))-;N-EPSILON-D-BIOTINYL-L-LYSINE;Biotinyl-L-lysine;L-BIOCYTIN;
PSA 158.85000
LogP 2.15940

Synthetic route

: N-(4-((S)-5'-oxo-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,2'-[1,3,2]oxazaborolidin]-4'-yl)butyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

: 576-19-2
biocytin

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 2h;	73%

: 56-87-1
L-lysine

: 91853-90-6
biotin chloride

: 576-19-2
biocytin

Conditions

Conditions	Yield
With sodium hydroxide; chloroform

: 857358-40-8
N2-formyl-N6-[5-((3aS)-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-valeryl]-L-lysine

: 576-19-2
biocytin

Conditions

Conditions	Yield
With hydrogenchloride

: 608-16-2
biotin methyl ester

: 576-19-2
biocytin

Conditions

Conditions	Yield
With toluene; 1,2,4-Trichlorobenzene

: 62062-43-5
Boc-Lys(biotinyl)-OH

: 576-19-2
biocytin

Conditions

Conditions	Yield
With methoxybenzene; trifluoroacetic acid

: 56-87-1
L-lysine

biotin-ethyl ester: biotin-ethyl ester

: 576-19-2
biocytin

Conditions

Conditions	Yield
With toluene; 1,2,4-Trichlorobenzene

: 35013-72-0
biotin N-Hydroxysuccinimide ester

: 576-19-2
biocytin

Conditions

Conditions	Yield
Stage #1: biotin N-Hydroxysuccinimide ester With sodium hydrogencarbonate In water; N,N-dimethyl-formamide Stage #2: With ethylenediaminetetraacetic acid In water
Multi-step reaction with 2 steps 1: sodium hydroxide / 1,4-dioxane; water / 20 °C / pH 8 - 8.5 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / 1,4-dioxane / 22 - 25 °C / pH 8 - 8.5 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 1 h / 22 - 25 °C View Scheme

: 19729-28-3
Nα-formyl-L-lysine

: 576-19-2
biocytin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: aqueous HCl View Scheme

: 91853-90-6
biotin chloride

: 576-19-2
biocytin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: toluene; 1,2,4-trichloro-benzene View Scheme
Multi-step reaction with 2 steps 1: pyridine 2: aqueous HCl View Scheme

: 1155-64-2
N6-[(benzyloxy)carbonyl]-L-lysine

: 576-19-2
biocytin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid anhydride / und Hydrieren des Reaktionsprodukts an Palladium 2: pyridine 3: aqueous HCl View Scheme

: 13734-28-6
Boc-Lys-OH

: 576-19-2
biocytin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Py, aq. NaOH 2: aq. CF3CO2H, anisole View Scheme

: 33755-53-2
D-(+)-biotin 2-nitrophenyl ester

: 576-19-2
biocytin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Py, aq. NaOH 2: aq. CF3CO2H, anisole View Scheme

: 62062-42-4
5-((3aS)-2-oxo-1-trifluoroacetyl-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid 4-nitro-phenyl ester

: 576-19-2
biocytin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. EtOH / Heating 2: Py, aq. NaOH 3: aq. CF3CO2H, anisole View Scheme

: 58-85-5
biotin

: 576-19-2
biocytin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 4-nitro-phenol, Py / 50 °C 2: aq. EtOH / Heating 3: Py, aq. NaOH 4: aq. CF3CO2H, anisole View Scheme
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C 2: sodium hydroxide / 1,4-dioxane; water / 20 °C / pH 8 - 8.5 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 1 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 22 - 25 °C 2: sodium hydroxide / 1,4-dioxane / 22 - 25 °C / pH 8 - 8.5 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 1 h / 22 - 25 °C View Scheme

: 146987-10-2
N-α-Fmoc-N-ε-biotinyl-L-lysine

: 576-19-2
biocytin

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 1h;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 22 - 25℃; for 1h;

: 56-87-1
L-lysine

: 58-85-5
biotin

: 576-19-2
biocytin

Conditions

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide In dichloromethane at 45℃; for 2h; pH=7.4;

: 192222-85-8
[CpFe(CO)2(η1-N-3-isothiocyanatophtalimidato)]

: 576-19-2
biocytin

: [CpFe(CO)2(NC8H3O2NHC(S)NHCH(COOH)(CH2)4NHCO(CH2)4C5H7N2OS)]

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide (Ar); stirring of soln. of CpFe(CO)2(NC8H3O2NCS), biocytin and Et3N in water at room temp. for 2 h; evapn. to dryness, dissolving in water, acidification to pH 3 with 0.6 MHCl, pptn., elem. anal.;	94%

: 57903-15-8
2-(methylsulfonyl)ethyl succinimidyl carbonate

: 576-19-2
biocytin

: (S)-2-(2-Methanesulfonyl-ethoxycarbonylamino)-6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile for 16h; Ambient temperature;	93%

: 192222-87-0
[CpFe(CO)2(η1-N-4-isothiocyanatophtalimidato)]

: 7732-18-5
water

: 576-19-2
biocytin

: [CpFe(CO)2(NC8H3O2NHC(S)NHCH(COOH)(CH2)4NHCO(CH2)4C5H7N2OS)] monohydrate

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide (Ar); stirring of soln. of CpFe(CO)2(NC8H3O2NCS), biocytin and Et3N in water at room temp. for 2 h; evapn. to dryness, dissolving in water, acidification to pH 3 with 0.6 MHCl, pptn., elem. anal.;	93%

...Expand

: 87736-89-8
1-<<4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoyl>oxy>-2,5-pyrrolidinedione

: 576-19-2
biocytin

: Nα-(4-(1-azi-2,2,2-trifluoroethyl)benzoyl)-L-biocytin

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide Ambient temperature;	91%

: 91990-88-4
p-benzoylbenzoic acid N-hydroxysuccinimide ester

: 576-19-2
biocytin

: 165898-24-8
Nα-(4-benzoylbenzoyl)-L-biocytin

Conditions

Conditions	Yield
With sodium hydroxide In water; N,N-dimethyl-formamide	90%
With sodium hydroxide In N,N-dimethyl-formamide Ambient temperature;	82%

: 126695-58-7
succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate

: 576-19-2
biocytin

: 165898-22-6
2-(4-azido-2,3,5,6-tetrafluorobenzamido)-6-[5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-6-yl)pentanamido]hexanoic acid

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 20℃;	89%
With sodium hydroxide In N,N-dimethyl-formamide Ambient temperature;	85%

: 125680-85-5
1-<<<2-nitro-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>phenoxy>acetyl>oxy>-2,5-pyrrolidinedione

: 576-19-2
biocytin

: 178484-35-0
(S)-2-{2-[2-Nitro-4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-acetylamino}-6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; N,N-dimethyl-formamide; acetonitrile for 1h; Ambient temperature;	89%

: 546094-91-1
[CpFe(CO)2(η1-N-4-isothiocyanatobenzenesulfonamido)]

: 7732-18-5
water

: 576-19-2
biocytin

: [CpFe(CO)2(NHSO2C6H4NHC(S)NHCH(COOH)(CH2)4NHCO(CH2)4C5H7N2OS)] thihydrate

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide (Ar); stirring of soln. of CpFe(CO)2(NHSO2C6H4NCS), biocytin and Et3N inwater at room temp. for 2 h; evapn. to dryness, dissolving in water, acidification to pH 3 with 0.6 MHCl, pptn., elem. anal.;	62%

...Expand

: 38050-71-4
9-methoxy-9-BBN

: 576-19-2
biocytin

: N-(4-((S)-5'-oxo-9λ4-boraspiro[bicyclo[3.3.1]nonane-9,2'-[1,3,2]oxazaborolidin]-4'-yl)butyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide

Conditions

Conditions	Yield
In methanol; hexane for 4h; Reflux;	58%

: 53053-08-0
4-azidobenzoic acid N-hydroxysuccinimide ester

: 576-19-2
biocytin

: C23H31N7O5S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 22 - 25℃;	30.4%
With N-ethyl-N,N-diisopropylamine at 20℃;

: 42855-00-5
nitroveratryloxycarbonyl chloride

: 576-19-2
biocytin

: (S)-2-(4,5-Dimethoxy-2-nitro-benzyloxycarbonylamino)-6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid

Conditions

Conditions	Yield
With sodium carbonate In tetrahydrofuran; water for 3h;

: 576-19-2
biocytin

: 249749-25-5
(S)-2-(4-Azido-2,3,5,6-tetrafluoro-benzoylamino)-6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / aq. NaOH / dimethylformamide / 20 °C 2: 77 percent / dicyclohexylcarbodiimide / dimethylformamide / 12 h / 20 °C View Scheme

: 576-19-2
biocytin

: 4-Azido-N-{(S)-1-(2-{2-[4-(4-chloro-2-fluoro-phenylamino)-6-methoxy-quinazolin-7-yloxy]-ethoxy}-ethylcarbamoyl)-5-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentyl}-2,3,5,6-tetrafluoro-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 89 percent / aq. NaOH / dimethylformamide / 20 °C 2: 77 percent / dicyclohexylcarbodiimide / dimethylformamide / 12 h / 20 °C 3: 98 percent / dimethylformamide / 12 h / 20 °C View Scheme

: 576-19-2
biocytin

: (S)-2-(4,5-Dimethoxy-2-nitro-benzyloxycarbonylamino)-6-[5-((3aR,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid cyanomethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium carbonate / H2O; tetrahydrofuran / 3 h 2: triethylamine / dimethylformamide View Scheme

: 576-19-2
biocytin

: 1-(N-(Nα-(4-benzoylbenzoyl)-L-biocytinoyl)amino)-6-(N'-pepstatinoylamino)hexane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 82 percent / aq. NaOH / dimethylformamide / Ambient temperature 2: 86 percent / diisopropylethylamine, HOAT, EDAC / dimethylformamide / Ambient temperature 3: HCl / dioxane / 1 h / Ambient temperature 4: diisopropylethylamine, HOAT, EDAC / dimethylformamide / Ambient temperature View Scheme

: 576-19-2
biocytin

: N-{(S)-1-(6-Amino-hexylcarbamoyl)-5-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentyl}-4-benzoyl-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 82 percent / aq. NaOH / dimethylformamide / Ambient temperature 2: 86 percent / diisopropylethylamine, HOAT, EDAC / dimethylformamide / Ambient temperature 3: HCl / dioxane / 1 h / Ambient temperature View Scheme

: 576-19-2
biocytin

: 165898-25-9
1-(N-(Nα-(4-benzoylbenzoyl)-L-biocytinoyl)amino)-6-(N'-boc-amino)hexane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / aq. NaOH / dimethylformamide / Ambient temperature 2: 86 percent / diisopropylethylamine, HOAT, EDAC / dimethylformamide / Ambient temperature View Scheme

: 576-19-2
biocytin

: 168639-65-4
{(S)-1-(2-Amino-ethylcarbamoyl)-5-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentyl}-carbamic acid 2-methanesulfonyl-ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / Et3N / H2O; acetonitrile / 16 h / Ambient temperature 2: 70 percent / Et3N, HOBt, CMC metho-p-toluene sulfonate / H2O; acetonitrile / 16 h / Ambient temperature 3: aq. TFA / Ambient temperature View Scheme

: 576-19-2
biocytin

: 168639-75-6
{(S)-1-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-5-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentyl}-carbamic acid 2-methanesulfonyl-ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / Et3N / H2O; acetonitrile / 16 h / Ambient temperature 2: 70 percent / Et3N, HOBt, CMC metho-p-toluene sulfonate / H2O; acetonitrile / 16 h / Ambient temperature View Scheme

: 576-19-2
biocytin

: {(S)-1-{2-[3-(4-Hydroxy-phenyl)-propionylamino]-ethylcarbamoyl}-5-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentyl}-carbamic acid 2-methanesulfonyl-ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / Et3N / H2O; acetonitrile / 16 h / Ambient temperature 2: 70 percent / Et3N, HOBt, CMC metho-p-toluene sulfonate / H2O; acetonitrile / 16 h / Ambient temperature 3: aq. TFA / Ambient temperature 4: 73 percent / DIPEA / acetonitrile; H2O / 20 h / Ambient temperature View Scheme

Biocytin Specification

The Biocytin with the cas number 576-19-2, is also called N~6~-{5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl}-L-lysine .The product y of this chemical is Biotin Derivatives .It is useful for the synthesis of Biocytin containing peptides to study the mechanism of reactions catalyzed by biotin - containing enzymes.

The properties of the Biocytin are: (1)#H bond acceptors: 8 ; (2)#H bond donors: 6 ; (3)#Freely Rotating Bonds: 12 ; (4)Polar Surface Area: 98.7 Å² ; (5)Index of Refraction: 1.547 ; (6)Molar Refractivity: 95.8 cm³ ; (7)Molar Volume: 301.7 cm³ ; (8)Polarizability: 37.98×10^-24cm³; (9)Surface Tension: 50.2 dyne/cm ; (10)Enthalpy of Vaporization: 118.65 kJ/mol ; (11)Vapour Pressure: 1.75×10^-24 mmHg at 25°C.

Biological activity of this chemical are: (1)Versatile marker used in anterograde, retrograde and intracellular neuroanatomical investigations and in biotinidase assays; (2)Displays high solubility in aqueous solutions and has a low molecular weight facilitating injection using micropipettes; (3) Can be incorporated with a variety of avidin and streptavidin conjugates for detection by light, fluorescence or electron microscope.

This product can be supplied by the following suppliers: (1)3B Pharmachem International (Wuhan) Co.,Ltd.; (2)Nanjing Chemlin Chemical Co., Ltd.; (3)Guangzhou WeiBo Chemical Co., Ltd.; (4)Leap Labchem Co.,Ltd.; (5)Advanced Technology & Industrial Co., Ltd.; (6)MOLEKULA Ltd. ; (7)Toronto Research Chemicals; (8)Medical Isotopes.

You can still convert the following datas into molecular structure :
1.O=C1N[C@@H]2[C@@H](SC[C@@H]2N1)CCCCC(=O)NCCCC[C@@H](C(=O)O)N
2.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

Product Name

Biocytin

Synthetic route

Biocytin Specification

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