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DBD-NCS [=4-(N,N-Dimethylaminosulfonyl)-7-isothiocyanato-2,1,3-benzoxadiazole] [for HPLC Labeling and Edman Degradation]
(CAS RN:147611-81-2 Product Number:A5575)

Structure

DBD-NCS
Synonym 4-(N,N-Dimethylaminosulfonyl)-7-isothiocyanatobenzofurazan
Synonym 4-(N,N-Dimethylaminosulfonyl)-7-isothiocyanato-2,1,3-benzoxadiazole

General Information

Product Number A5575

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Purity/Analysis Method
Storage Temperature 0-10°C
M.F. / M.W. C9H8N4O3S2=284.31
CAS RN 147611-81-2
Related CAS RN
MDL Number MFCD03844763
Packaging and Container
  • Product Details
  • Safety & Regulations

Specification

Elemental analysis(Nitrogen) 19.1 to 20.0 %
Melting point 124.0 to 128.0 deg-C
Effect test of HPLC derivatization Effective as labeling agent for L-Phenylalanine

References

Reaxys-RN 7384123
PubChem SID 87563192

GHS

Pictogram
Signal Word Warning
Hazard Statements
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
Precautionary Statements
  • P264
  • :Wash hands and face thoroughly after handling.
  • P280
  • :Wear protective gloves, eye protection.
  • P302+P352+P332+P313+P362+P364
  • :IF ON SKIN: Wash with plenty of water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.
  • P305+P351+P338+P337+P313
  • :IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

Transport Information

HS Number 2934999090

Application

HPLC Labeling Reagent for Amines

The compound 1 is an HPLC fluorescence labeling reagent, which has a 2,1,3-benzoxadiazole skeleton and an isothiocyano group, and easily reacts with an amino group to form the corresponding thiourea. The resultant thiourea is stable enough to reach the detector without any decomposition under reversed phase HPLC. An excellent chromatogram can be obtained by fluorescence detection at the excitation and emission wavelengths of 384 nm and 520 nm, respectively. The detection limit for its quantity is an order of sub-picomol (S/N = 3). 1 itself does not fluoresce but shows an excellent stability in forms of both crystal and solution, and its derivatives are also stable. This compound can be used for amino acid sequence analysis (Edman Degradation) by binding with the N-terminal amino acid of peptides or proteins, followed by acid reatment.

Application example:
[Method by Manual Edman Degradation]
Peptide (insulin Chain B 500 pmol)
   │
   │ ・ Dissolve in 20 μL of 50% pyridine / H2O.
   │ ・ Add 5 μL of 1% triethylamine / CH3CN and 10 μL of 20 mM HPLC labeling reagent 1 / pyridine,
   │   and react the mixture at 50 ºC for 15 min under the atmosphere of inert gas.
   │ ・ After cooling to room temperature, wash the reactant solution 3 times
   │   with 200 μL of heptane / dichlorormethane (6/4).
   │ ・ Dry the washed solution at 50 ºC for 15 min by using a centrifugation evaporator.
   │ ・ Add 30 μL of 1% BF3•Et2O / CH3CN to the mixture and incubate the mixture at 50 ºC for 5 min.
   │ ・ Further dry the reactant solution under nitrogen gas.
   │ ・ Add 20 μL of H2O, and then extract 2 times with 100 μL of benzene / AcOEt (1/4).
   │
   │―――――(Aqueous phase) A peptide will be eluted out.
   │
  (Organic phase)
   │
   │ ・ Dry the extracted organic phase under nitrogen gas.
   │ ・ Dissolve the mixture in 2 μL of CH3CN.
   │ ・ Add 8 μL of 0.4 M HCl and hydrolyze the mixture at 50 ºC for 5 min.
   │ ・ Treat the reactant with 5 μL of 4 M HCl and 0.5 M NaNO2 at room temperature for 10 min
   │   and oxidize it.
   │ ・ Neutralize the reactant with 23 μL of 1 M NaNO2, and remove an excessive oxidant
   │   by adding 20 μL of 0.15 M methionine.
   │  
  Use 20 μL of this solution as an HPLC sample solution.

References

PubMed Literature

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