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CAS RN: 147611-81-2 | Product Number: A5575

DBD-NCS [=4-(N,N-Dimethylaminosulfonyl)-7-isothiocyanato-2,1,3-benzoxadiazole] [for HPLC Labeling and Edman Degradation]


Purity:
Synonyms:
  • 4-(N,N-Dimethylaminosulfonyl)-7-isothiocyanatobenzofurazan
  • 4-(N,N-Dimethylaminosulfonyl)-7-isothiocyanato-2,1,3-benzoxadiazole
Documents:
100MG
€227.00
2   4  

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Product Number A5575
Molecular Formula / Molecular Weight C__9H__8N__4O__3S__2 = 284.31  
Physical State (20 deg.C) Solid
Storage Temperature 0-10°C
Condition to Avoid Heat Sensitive
CAS RN 147611-81-2
Reaxys Registry Number 7384123
PubChem Substance ID 87563192
MDL Number

MFCD03844763

Specifications
Appearance Light orange to Yellow to Green powder to crystal
Elemental analysis(Nitrogen) 19.1 to 20.0 %
Melting point 124.0 to 128.0 °C
Effect test of HPLC derivatization Effective as labeling agent for L-Phenylalanine
Properties (reference)
Melting Point 126 °C
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
Related Laws: / Compliance with laws, Regulations
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 °C 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 °C 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 °C 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 °C 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.

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