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
NACRES:
NA.26
PubChem Substance ID:
UNSPSC Code:
12352209
EC Number:
250-093-9
MDL number:
Beilstein/REAXYS Number:
2124001
Product Name
2-Nitro-5-thiocyanatobenzoic acid, powder
InChI key
NQUNIMFHIWQQGJ-UHFFFAOYSA-N
InChI
1S/C8H4N2O4S/c9-4-15-5-1-2-7(10(13)14)6(3-5)8(11)12/h1-3H,(H,11,12)
SMILES string
OC(=O)c1cc(SC#N)ccc1[N+]([O-])=O
assay
≥98% (HPLC)
form
powder
color
yellow
mp
156-157 °C (lit.)
storage temp.
2-8°C
Quality Level
Related Categories
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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
J M Litersky et al.
The Biochemical journal, 316 ( Pt 2), 655-660 (1996-06-01)
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Maya Belghazi et al.
Molecular and cellular endocrinology, 247(1-2), 175-182 (2006-02-07)
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J Wu et al.
Analytical biochemistry, 235(2), 161-174 (1996-03-15)
A simple methodology has been developed to characterize the number and location of free cysteine and cystine groups in peptides and proteins, using chemical modification and matrix-assisted laser desorption/ ionization time-of flight mass spectrometry (MALDITOF MS). This new approach employs
Henning Koehn et al.
Journal of proteomics, 73(2), 323-330 (2009-10-03)
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