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N7009

Sigma-Aldrich

2-Nitro-5-thiocyanato-benzoesäure

≥98% (HPLC)

Synonym(e):

2-Nitro-5-thiocyanobenzoesäure, NTCB

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About This Item

Lineare Formel:
O2NC6H3(SCN)CO2H
CAS-Nummer:
30211-77-9
Molekulargewicht:
224.19
Beilstein:
2124001
EG-Nummer:
250-093-9
MDL-Nummer:
MFCD00007139
UNSPSC-Code:
12352209
PubChem Substanz-ID:
24897806
NACRES:
NA.26

product name

2-Nitro-5-thiocyanato-benzoesäure, powder

Assay

≥98% (HPLC)

Qualitätsniveau

200

Form

powder

Farbe

yellow

mp (Schmelzpunkt)

156-157 °C (lit.)

Lagertemp.

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)

InChIKey

NQUNIMFHIWQQGJ-UHFFFAOYSA-N

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Anwendung


  • 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. Wirkung

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

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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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 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
J M Litersky et al.
The Biochemical journal, 316 ( Pt 2), 655-660 (1996-06-01)
Phosphorylation of tau protein at Ser-262 has been shown to diminish its ability to bind to taxol-stabilized microtubules. The paired helical filaments (PHFs) found in Alzheimer's disease brain are composed of PHF-tau, which is hyperphosphorylated at multiple sites including Ser-262.
H J Shin et al.
Biochemical and biophysical research communications, 271(3), 801-806 (2000-05-18)
Acetolactate synthase (ALS) is the common enzyme in the biosynthesis of valine, leucine, and isoleucine. The role of four cysteinyl residues in tobacco ALS was determined using site-directed mutagenesis and cysteine-specific cleavage. The C411A mutation abolished the enzymatic activity, as
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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