N7009
2-Nitro-5-thiocyanatobenzoic acid
≥98% (HPLC)
Synonym(s):
2-Nitro-5-thiocyanobenzoic acid, NTCB
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About This Item
Linear Formula:
O2NC6H3(SCN)CO2H
CAS Number:
Molecular Weight:
224.19
Beilstein:
2124001
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26
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product name
2-Nitro-5-thiocyanatobenzoic acid, powder
Assay
≥98% (HPLC)
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
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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
Hsin-Yao Tang et al.
Analytical biochemistry, 334(1), 48-61 (2004-10-07)
The reagent 2-nitro-5-thiocyanatobenzoic acid (NTCB) is commonly used to cyanylate and cleave proteins at cysteine residues, but this two-step reaction requires lengthy incubations and produces highly incomplete cleavages. In previous reports, incomplete cleavage was attributed to a competing beta-elimination reaction
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
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