| Identification | More | [Name]
BIOTIN-NHS | [CAS]
35013-72-0 | [Synonyms]
5-(2-OXO-HEXAHYDRO-THIENO[3,4-D]IMIDAZOL-6-YL)-PENTANOIC ACID 2,5-DIOXO-PYRROLIDIN-1-YL ESTER
BIOTIN (LONG ARM) NHS
BIOTIN-NHS
BIOTIN-N-HYDROXYSUCCINIMIDE
(+)-BIOTIN-N-HYDROXYSUCCINIMIDE ESTER
BIOTIN-N-HYDROXYSUCCINIMIDE ESTER
(+)-BIOTIN N-SUCCINIMIDYL ESTER
BIOTIN-OSU
BIOTIN SE
BIOTIN SUCCINIMIDYL ESTER
BIOTINYL-N-HYDROXY-SUCCINIMIDE
(+)-BIOTINYL-N-SUCCINIMIDYL ESTER
BNHS
D-(+)BIOTIN N-HYDROXYSUCCINIMIDE ESTER
D-BIOTIN-N-HYDROXYSUCCINIMIDE ESTER
D-BIOTIN, SE
D-BIOTIN, SUCCINIMIDYL ESTER
D-BIOTINYL-OSU
NHS-BIOTIN
NHS-D-BIOTIN | [EINECS(EC#)]
609-055-0 | [Molecular Formula]
C14H19N3O5S | [MDL Number]
MFCD00078531 | [Molecular Weight]
341.38 | [MOL File]
35013-72-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
212-214 °C
| [density ]
1.45±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
DMF: ≤50 mg/mL Stable for at least one month in dry DMF
| [form ]
powder
| [pka]
13.89±0.40(Predicted) | [color ]
White to off-white | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Usage]
Amino reactive biotin reagent for preparing biotinylated surfaces or polypeptides. | [BRN ]
4720781 | [InChI]
InChI=1S/C14H19N3O5S/c18-10-5-6-11(19)17(10)22-12(20)4-2-1-3-9-13-8(7-23-9)15-14(21)16-13/h8-9,13H,1-7H2,(H2,15,16,21)/t8-,9-,13-/m0/s1 | [InChIKey]
YMXHPSHLTSZXKH-RVBZMBCESA-N | [SMILES]
C1(=O)N[C@]2([H])[C@H](CCCCC(ON3C(=O)CCC3=O)=O)SC[C@]2([H])N1 | [CAS DataBase Reference]
35013-72-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [F ]
10-23 | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Description]
N-Hydroxysuccinimide (NHS) activates carboxylic acid groups (on biotin) to facilitate coupling reactions. Biotin-NHS is a compound used to attach biotin to primary amines under alkaline conditions (pH~8-9). For example, lysines on the surface of proteins, including antibodies, are ideal targets for biotinylation with this compound. | [Chemical Properties]
White Solid | [Uses]
amine reactive biotinylation reagent | [Uses]
Amino reactive biotin reagent for preparing biotinylated surfaces or polypeptides. | [Uses]
Biotin-NHS is used in the biotinylation of proteins and peptides. Couples with primary amine in the pH range 6.5-8.5.
| [reaction suitability]
reaction type: Biotinylations | [Synthesis]
GENERAL STEPS: To a mixed solution of D-biotin (0.82 mmol, 200 mg) and N-hydroxybutanediimide (0.89 mmol, 102 mg) was added 3-(ethyliminomethylamino)-N,N-dimethylpropan-1-amine hydrochloride (0.96 mmol, 184 mg). The reaction mixture was stirred at room temperature overnight and then concentrated to give a white solid. The crude product was mixed with isopropanol, heated to 70 °C and cooled. The pure product was obtained by filtration as a white powder in 91% yield (0.75 mmol, 255 mg). | [Purification Methods]
Recrystallise the ester from refluxing isoPrOH and dry it in a vacuum over P2O5 + KOH. [Jasiewicz et al. Exp Cell Biol 100 213 1976.] | [References]
[1] Journal of the American Chemical Society, 2007, vol. 129, # 45, p. 13987 - 13996
[2] New Journal of Chemistry, 2013, vol. 37, # 11, p. 3762 - 3769
[3] Organic Letters, 2013, vol. 15, # 16, p. 4130 - 4133
[4] Journal of Materials Chemistry, 2004, vol. 14, # 17, p. 2638 - 2642
[5] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 784 - 791 |
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