Norbornene-PEG-Biotin (Norb-Bio) Probe
The norbornene-PEG-biotin (norb-bio) probe is a cysteine sulfenic acid trap for use on proteins and live cells to study the effects of oxidative stress.
The strained alkene reacts selectively with sulfenic acids through a strain-promoted group transfer reaction to yield a sulfoxide product. The biotin tag is incorporated for ease of enrichment and detection in protein and cell assay applications using various streptavidin systems (eg. western blot, affinity purification). The norb-bio probe is able to detect oxidized proteins in live cells through both endogenous and exogenous (eg. addition of H2O2) introduction of ROS.
From the laboratory of Justin M. Chalker, PhD, Flinders University.
The norbornene-PEG-biotin (norb-bio) probe is a cysteine sulfenic acid trap for use on proteins and live cells to study the effects of oxidative stress.
The strained alkene reacts selectively with sulfenic acids through a strain-promoted group transfer reaction to yield a sulfoxide product. The biotin tag is incorporated for ease of enrichment and detection in protein and cell assay applications using various streptavidin systems (eg. western blot, affinity purification). The norb-bio probe is able to detect oxidized proteins in live cells through both endogenous and exogenous (eg. addition of H2O2) introduction of ROS.
From the laboratory of Justin M. Chalker, PhD, Flinders University.
| Product Type: | Small Molecule |
| Name: | Norb-bio |
| Chemical Formula: | C24H38N4O5S |
| Molecular Weight: | 494.65 g/mol |
| Format: | White to off-white solid |
| Solubility: |
Soluble in MeOH and DMSO (≤300 mM), Soluble in aqueous (eg. buffer) after pre-solubilizing in DMSO (up to 300 mM) for final concentration in aqueous of 6 mM at 2 %v/v DMSO or less. |
| Spectral Information: |
IR (νmax, ATR): 3291, 2942, 2869, 1703, 1639, 1551, 1464, 1309, 1248, 1214, 1129, 987, 867, 724 cm–1 1H NMR (600 MHz, MeOD): δ = 6.14 (2H, m, CHCH=CHCH), 4.49 (1H, dd, J = 8.3, 4.5 Hz, CONHCHCH2S), 4.30 (1H, dd, J = 7.9, 4.4 Hz, CONHCHCHS), 3.62 (4H, m, 2 x CH2 PEG), 3.55 (4H, m, 2 x CH2 PEG), 3.37 (4H, m, 2 x CH2 PEG), 3.20 (1H, m, SCH), 2.93 (1H, dd, J = 12.8, 5.0 Hz, CONHCHCHAHBS), 2.87 (2H, m, CHCH=CHCH), 2.71 (1H, d, J = 12.7 Hz, CONHCHCHAHBS), 2.22 (2H, t, J = 7.1 Hz, CH2CONH), 2.13 (1H, m, CH=CHCHCH), 1.87 (1H, dt, J = 11.7, 4.0 Hz, CH=CHCHCHAHB), 1.77-1.57 (5H, contains 2 x CH2 Biotin and CHCHAHBCH), 1.44 (2H, p, J = 7.5 Hz, CH2 Biotin), 1.31 (2H, contains CH=CHCHCHAHB and CHCHAHBCH) 13C NMR (150 MHz, MeOD): δ = 178.6, 176.2, 166.1, 139.0, 137.3, 71.3, 70.7, 70.6, 63.4, 61.6, 57.0, 48.6 (overlaps with NMR solvent peak), 47.1, 45.2, 42.8, 41.0, 40.4, 40.3, 36.7, 31.2, 29.8, 29.5, 26.8; |
| Melting Point: | 126-131C |
| Rf Value: | 10% MeOH in DCM, 0.32 |
| Storage: | -20C |
| Shipped: | Room temperature |
- Alcock LJ, Farrell KD, Akol MT, Jones GMH, Tierney M, Kramer HB, Pukala TL, Bernardes GJL, Perkins MV, Chalker JM, Norbornene probes for the study of cysteine oxidation, Tetrahedron, 2018, 74, 1220-1228.
- Alcock LJ, Oliveira BL, Deery MJ, et al. Norbornene Probes for the Detection of Cysteine Sulfenic Acid in Cells. ACS Chem Biol. 2019;14(4):594-598.
- Alcock LJ, Langini M, Stühler K, et al. Proteome-Wide Survey of Cysteine Oxidation by Using a Norbornene Probe. Chembiochem. 2020;21(9):1329‐1334.
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