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Biotin-ONp Novabiochem®
Sigma-Aldrich
8.51027
Biotin-ONp
(+)-Biotin 4-nitrophenyl ester 98%
Sigma-Aldrich
861650
(+)-Biotin 4-nitrophenyl ester
NHS-dPEG®4-biotin
Sigma-Aldrich
QBD10200
NHS-dPEG®4-biotin
Biotin-NHS
Sigma-Aldrich
203112
Biotin-NHS
Novabiochem®
98%

Description

Synonyms
Biotin-ONp, Biotin p-nitrophenyl ester,5-(2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid p-nitrophenyl ester
4-Nitrophenyl (+)-biotinate, d-Biotin p-nitrophenyl ester, BNP
(+)-Biotin-PEO4-NHS-propionate, NHS-PEO4-Biotin, Polyethylene glycol
Biotin-NHS, Biotin N-hydroxysuccinimide Ester
CAS Number
33755-53-2
33755-53-2
459426-22-3
35013-72-0
Molecular Formula
Empirical Formula (Hill Notation)
: C16H19N3O5S
Empirical Formula (Hill Notation)
: C16H19N3O5S
Empirical Formula (Hill Notation)
: C25H40N4O10S
Empirical Formula (Hill Notation)
: C14H19N3O5S
Molecular Weight
: 365.40
Molecular Weight
: 365.40
Molecular Weight
: 588.67
Molecular Weight
: 341.38
MDL Number
MFCD15141972
MFCD15141972
MFCD00078531
Quality Designations
200
100

Properties

Assay:
≥97.0% (HPLC)
≥98% (TLC)
Assay:
98%
Assay:
>90%
Assay:
≥90% (NMR)
color:
color:
color:
color:
white to off-white
functional group:
functional group:
ester
nitro
thioether
functional group:
functional group:
shipped in:
shipped in:
shipped in:
ambient
shipped in:
ambient
InChI:
1S/C16H19N3O5S/c20-14(24-11-7-5-10(6-8-11)19(22)23)4-2-1-3-13-15-12(9-25-13)17-16(21)18-15/h5-8,12-13,15H,1-4,9H2,(H2,17,18,21)/t12-,13-,15-/m0/s1
InChI:
1S/C16H19N3O5S/c20-14(24-11-7-5-10(6-8-11)19(22)23)4-2-1-3-13-15-12(9-25-13)17-16(21)18-15/h5-8,12-13,15H,1-4,9H2,(H2,17,18,21)/t12-,13-,15-/m0/s1
InChI:
1S/C25H40N4O10S/c30-20(4-2-1-3-19-24-18(17-40-19)27-25(34)28-24)26-8-10-36-12-14-38-16-15-37-13-11-35-9-7-23(33)39-29-21(31)5-6-22(29)32/h18-19,24H,1-17H2,(H,26,30)(H2,27,28,34)/t18-,19-,24-/m0/s1
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)
InChI key:
YUDNXDTXQPYKCA-YDHLFZDLSA-N
InChI key:
YUDNXDTXQPYKCA-YDHLFZDLSA-N
InChI key:
DTLVBHCSSNJCMJ-JXQFQVJHSA-N
InChI key:
YMXHPSHLTSZXKH-UHFFFAOYSA-N
manufacturer/tradename:
Novabiochem®
manufacturer/tradename:
manufacturer/tradename:
manufacturer/tradename:
Calbiochem®
application(s):
peptide synthesis
application(s):
application(s):
application(s):
mp:
163-165 °C
mp:
163-165 °C (lit.)
mp:
mp:
optical activity:
optical activity:
[α]25/D +51°, c = 2 in DMF: AcOH (99:1)
optical activity:
optical activity:
form:
powder
form:
powder
form:
solid or viscous liquid
form:
solid
polymer architecture:
polymer architecture:
polymer architecture:
shape: linear
functionality: monofunctional
polymer architecture:
product line:
Novabiochem®
product line:
product line:
product line:
reaction suitability:
reaction type: Biotinylations
reaction suitability:
reaction suitability:
reagent type: cross-linking reagent
reaction type: Biotinylations
reactivity: amine reactive
reagent type: linker
reaction suitability:
SMILES string:
S1[C@H]([C@H]3NC(=O)N[C@H]3C1)CCCCC(=O)Oc2ccc(cc2)[N+](=O)[O-]
SMILES string:
[O-][N+](=O)c1ccc(OC(=O)CCCC[C@@H]2SCC3NC(=O)NC23)cc1
SMILES string:
O=C(ON1C(CCC1=O)=O)CCOCCOCCOCCOCCNC(CCCCC2C3NC(NC3CS2)=O)=O
SMILES string:
S1C(C3NC(=O)NC3C1)CCCCC(=O)ON2C(=O)CCC2=O
solubility:
solubility:
methanol: 25 mg/mL, clear, colorless to greenish-yellow
solubility:
solubility:
DMSO: 100 mg/mL
storage condition:
storage condition:
storage condition:
storage condition:
OK to freeze
desiccated
storage temp.:
15-25°C
storage temp.:
storage temp.:
−20°C
storage temp.:
2-8°C
Quality Level:
200
Quality Level:
Quality Level:
Quality Level:
100

Usage and Safety

Application
  • Mechanistic studies of a cell-permeant peptide designed to enhance myosin light chain phosphorylation: This study discusses the synthesis and applications of cell-permeant peptides involving biotin-ONP for enhanced cellular processes (Almansour, 2017).
  • Structure-function analysis of tight junction-directed permeation enhancer PIP250: Provides insights into the utility of biotin-ONP in analyzing the structure and function of peptides used to enhance cellular permeation (Taverner et al., 2023).
(+)-Biotin 4-nitrophenyl ester may be used in the preparation of biotin tagged ARC (adenosine-oligoarginine conjugate) derivative during cellular protein uptake studies. It may also be used to prepare biotinylated quinazoline derivatives, which shows inhibitory activities against VEGFR-2 (vascular endothelial growth factor receptor-2) tyrosine kinase. (+)-Biotin 4-nitrophenyl ester undergoes hydrolysis in the presence of Na[17O]H to form [17O2]biotin, which can be used in solid-state 17O NMR spectroscopic experiments to analyze large protein-ligand complexes.

Automate your Biotin tagging with Synple Automated Synthesis Platform (SYNPLE-SC002)
Risk and Safety
Storage Class Code:

11 - Combustible Solids

WGK:

WGK 3

Flash Point(F):

Not applicable

Flash Point(C):

Not applicable

Storage Class Code:

11 - Combustible Solids

WGK:

WGK 3

Flash Point(F):

Not applicable

Flash Point(C):

Not applicable

Personal Protective Equipment:

Eyeshields, Gloves, type N95 (US)

Storage Class Code:

11 - Combustible Solids

Flash Point(F):

Not applicable

Flash Point(C):

Not applicable

Storage Class Code:

11 - Combustible Solids

WGK:

WGK 3

Flash Point(F):

Not applicable

Flash Point(C):

Not applicable