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B4651

Sigma-Aldrich

3-Bromo-3-methyl-2-(2-nitrophenylthio)-3H-indole

≥85%

Synonym(s):

2-(2-Nitrophenylsulfenyl)-3-methyl-3-bromoindolenine, 3-Bromo-3-methyl-2-(2-nitrophenylmercapto)-3H-indole, BNPS-skatol

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About This Item

Empirical Formula (Hill Notation):
C15H11BrN2O2S
CAS Number:
27933-36-4
Molecular Weight:
363.23
Beilstein/REAXYS Number:
1491457
EC Number:
248-737-9
MDL number:
MFCD00037978
UNSPSC Code:
12352200
PubChem Substance ID:
24891797

assay

≥85%

storage temp.

−20°C

SMILES string

CC1(Br)C(Sc2ccccc2[N+]([O-])=O)=Nc3ccccc13

InChI

1S/C15H11BrN2O2S/c1-15(16)10-6-2-3-7-11(10)17-14(15)21-13-9-5-4-8-12(13)18(19)20/h2-9H,1H3

InChI key

BXTVQNYQYUTQAZ-UHFFFAOYSA-N

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Application

Peptide cleavage reagent specific for the carboxyl side of tryptophan residues.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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V Rahali et al.
Journal of protein chemistry, 18(1), 1-12 (1999-03-11)
A comparative study of various procedures for tryptophanyl peptide bond cleavage by BNPS-skatole [2-(2-nitrophenyl)-3-methyl-3-bromoindolenine] was carried out on native and on reduced and alkylated bovine beta-lactoglobulin (BLG). The reaction yield and the composition of the derived products were studied in
J E Moskaitis et al.
Neurochemical research, 11(2), 299-315 (1986-02-01)
The interactions of sodium dodecyl sulfate with a number of proteins were examined at a variety of pH values ranging from 4.8 to 11.6. The dodecyl sulfate-induced precipitation of some of these proteins was observed within a relatively limited range
Hee-Kyoung Lee et al.
Biochemical and biophysical research communications, 315(1), 1-9 (2004-03-12)
Squalene epoxidase (SE) catalyzes the conversion of squalene to (3S)-2,3-oxidosqualene. Photolabeling and site-directed mutagenesis were performed on recombinant rat SE (rrSE) in order to identify the location of the substrate-binding site and the roles of key residues in catalysis. Truncated
H Xue et al.
Biochemistry and cell biology = Biochimie et biologie cellulaire, 75(6), 709-715 (1997-01-01)
A concerted conformational change in Bacillus subtilis tryptophanyl-tRNA synthetase (TrpRS) was evident from previous fluorescence on the quenching of the single Trp residue Trp-92 in the 4FTrp-AMP complexed enzyme. In this study, chemical modifications of the B. subtilis TrpRS were
M M Vestling et al.
Rapid communications in mass spectrometry : RCM, 8(9), 786-790 (1994-09-01)
Mass spectrometry has been used to define the reaction of BNPS-skatole (3-bromo-3-methyl-2-(o-nitrophenylsulfenyl)indolenine) with selected proteins and peptides, confirming the cleavage of the protein chain at tryptophan residues, characterizing the products, and identifying the side reactions. A short procedure for carrying
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