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CAS RN: 163927-32-0 | Product Number: A5569

(S)-(+)-DBD-Py-NCS [=(S)-(+)-4-(N,N-Dimethylaminosulfonyl)-7-(3-isothiocyanatopyrrolidin-1-yl)-2,1,3-benzoxadiazole] [for HPLC Labeling]


Purity: >98.0%(HPLC)
Synonyms:
  • (S)-(+)-4-(N,N-Dimethylaminosulfonyl)-7-(3-isothiocyanatopyrrolidin-1-yl)benzofurazan
  • (S)-(+)-4-(N,N-Dimethylaminosulfonyl)-7-(3-isothiocyanatopyrrolidin-1-yl)-2,1,3-benzoxadiazole
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Product Number A5569
Purity / Analysis Method >98.0%(HPLC)
Molecular Formula / Molecular Weight C__1__3H__1__5N__5O__3S__2 = 353.42  
Physical State (20 deg.C) Solid
Storage Temperature 0-10°C
Store Under Inert Gas Store under inert gas
Condition to Avoid Air Sensitive,Heat Sensitive
CAS RN 163927-32-0
PubChem Substance ID 87563186
MDL Number

MFCD00671494

Specifications
Appearance Light yellow to Brown powder to crystal
Purity(HPLC) min. 98.0 area%
Melting point 157.0 to 161.0 °C
Properties (reference)
Specific Rotation 285° (C=0.4,CH3CN)
GHS
Related Laws: / Compliance with laws, Regulations
Transport Information:
HS Number 2935909099
Application
HPLC Labeling Reagent for Chiral Amines and Thiols

The compound 1 is an HPLC fluorescence labeling reagent for optical purity determination. This compound easily reacts with amino or mercapto groups, which are directly linked to the asymmetric carbon atom and produces diastereomers of thiourea or dithiocarbamate. These diasteromers can be separated by reversed phase HPLC, and an excellent chromatogram can be obtained by fluorescence detection at the excitation and emission wavelengths of 460 nm and 550 nm, respectively. [The detection limit: thiopronine = 0.5 pmol (S/N = 2)]
Since both (R)- and (S)-isomers of the derivatization reagents are commercially available on the market, it is possible to change an elution order of the derivatized diastereomers by selecting either enantiomer of the derivatization reagent. Thus, an enantiomer of the aminocompound, whose existing quantity is very small, can be eluted out first and quantified with a high precision. Moreover, there are reports for the application of these somers to Edman Degradation.

Application example:
Add 10 µL of 5 mM HPLC labeling reagent 1 / acetonitrile solution in 10 µL of 1 mM amine / acetnitrile-H2O (1:1) solution (containing 2% triethylamine) to a vessel, close the cap of the reaction vessel and incubate the mixture at 55 °C for 10 min. Then, add 480 µL of a mixture solution of 1 M acetic acid and acetnitrile-H2O (1:1) solution, and dilute this reactant mixture 10x by acetonitrile. Use 5 µL of this diluted solution as an HPLC sample solution.

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