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.

Catalog Number Product DataSheet Size AVAILABILITY Price Qty
EFL008
Norbornene-PEG-Biotin (Norb-Bio) Probe
10mg In stock
Regular Price:$220.00
On Sale:
Specifications

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

Provider
From the laboratory of Justin M. Chalker, PhD, Flinders University.
Comments
Recommended between 1-3 mM concentration depending on application and sample volume. Norb-bio can be prepared as a < 300 mM solution in DMSO for direct labelling applications on proteins, cell lysates, and in living cells.
References
  1. 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.
  2. 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.
  3. 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.

If you publish research with this product, please let us know so we can cite your paper.

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