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N7009

Sigma-Aldrich

2-Nitro-5-thiocyanatobenzoic acid

≥98% (HPLC)

Sinónimos:

2-Nitro-5-thiocyanobenzoic acid, NTCB

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About This Item

Fórmula lineal:
O2NC6H3(SCN)CO2H
Número de CAS:
30211-77-9
Peso molecular:
224.19
Beilstein/REAXYS Number:
2124001
EC Number:
250-093-9
MDL number:
MFCD00007139
UNSPSC Code:
12352209
PubChem Substance ID:
24897806
NACRES:
NA.26

product name

2-Nitro-5-thiocyanatobenzoic acid, powder

assay

≥98% (HPLC)

Quality Level

200

form

powder

color

yellow

mp

156-157 °C (lit.)

storage temp.

2-8°C

SMILES string

OC(=O)c1cc(SC#N)ccc1[N+]([O-])=O

InChI

1S/C8H4N2O4S/c9-4-15-5-1-2-7(10(13)14)6(3-5)8(11)12/h1-3H,(H,11,12)

InChI key

NQUNIMFHIWQQGJ-UHFFFAOYSA-N

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Application


  • Site-Specific Conversion of Cysteine in a Protein to Dehydroalanine Using 2-Nitro-5-thiocyanatobenzoic Acid: This research demonstrates the use of 2-Nitro-5-thiocyanatobenzoic acid in protein engineering to modify cysteine residues, which is critical for developing therapeutic proteins and understanding protein structure-function relationships (Qiao et al., 2021).

  • Scrapie prion protein structural constraints obtained by limited proteolysis and mass spectrometry: Highlights the utility of 2-Nitro-5-thiocyanatobenzoic acid in the study of prion proteins, providing insights into protein misfolding diseases which can lead to novel therapeutic approaches (Sajnani et al., 2008).

  • Localization of a substrate binding domain of the human reduced folate carrier to transmembrane domain 11 by radioaffinity labeling and cysteine-substituted accessibility methods: Utilizes 2-Nitro-5-thiocyanatobenzoic acid in biochemical assays to understand transporter proteins, essential for drug delivery and targeting (Hou et al., 2005).

  • A novel procedure for the preparation of biologically active recombinant peptides using a cyanylation reaction: Describes a method using 2-Nitro-5-thiocyanatobenzoic acid for peptide synthesis, beneficial for the development of peptide-based pharmaceuticals (Koyama et al., 1994).

Biochem/physiol Actions

2-nitro-5-thiocyanatobenzoic acid (NTCB) is commonly used to cyanylate and cleave proteins at cysteine residues.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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R Daniel et al.
The Journal of biological chemistry, 272(43), 26934-26939 (1997-10-27)
Escherichia coli dihydroorotase contains six cysteines/subunit, which are potential ligands of structural and catalytic zinc metals at protein sites of the enzyme. Specific thiol reagents modify, in nondenaturing conditions only, two of these cysteines; these two residues are thought to
Maya Belghazi et al.
Molecular and cellular endocrinology, 247(1-2), 175-182 (2006-02-07)
Luteinizing hormone (LH) like all other glycoprotein hormones is composed of two dissimilar subunits, alpha and beta, that are non-covalently associated. The heterodimer is stabilized by a region of the beta-subunit called the "seatbelt" because it wraps around the alpha-subunit
J Bubis et al.
Archives of biochemistry and biophysics, 395(2), 146-157 (2001-11-08)
Modification of transducin (T) with iodoacetic acid (IAA) inhibited its light-dependent guanine nucleotide-binding activity. Approximately 1 mol of [(3)H]IAA was incorporated per mole of T. Cys(347), located on the alpha-subunit of T (T(alpha)), was identified as the major labeled residue
Z Xie et al.
Journal of neurochemistry, 93(4), 1038-1046 (2005-04-29)
Apolipoprotein J (apoJ; also known as clusterin and sulfated glycoprotein (SGP)-2) is associated with senile plaques in degenerating regions of Alzheimer's disease brains, where activated microglia are also prominent. We show a functional link between apoJ and activated microglia by
N Tanaka et al.
Biochemistry, 40(20), 5914-5920 (2001-05-16)
We investigated the pressure effect on the conformation of beta-amylase by monitoring the chemical reaction of the unpaired cysteine. Sweet potato beta-amylase is composed of four identical subunits, each of which contains six cysteine residues. These residues are inert to
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