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(R)-(-)-DBD-Py-NCS [=(R)-(-)-4-(N,N-Dimethylaminosulfonyl)-7-(3-isothiocyanatopyrrolidin-1-yl)-2,1,3-benzoxadiazole] [for HPLC Labeling]
(CAS RN:163927-31-9 Product Number:A5568)

Structure

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(R)-(-)-DBD-Py-NCS
Synonym (R)-(-)-4-(N,N-Dimethylaminosulfonyl)-7-(3-isothiocyanatopyrrolidin-1-yl)benzofurazan
Synonym (R)-(-)-4-(N,N-Dimethylaminosulfonyl)-7-(3-isothiocyanatopyrrolidin-1-yl)-2,1,3-benzoxadiazole

General Information

Product Number A5568

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Purity/Analysis Method >98.0%(HPLC)
Storage Temperature 0-10°C
M.F. / M.W. C13H15N5O3S2=353.42
CAS RN 163927-31-9
Related CAS RN
MDL Number MFCD00671493
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Specification

Purity(HPLC) min. 98.0 area%
Optical purity(LC) min. 99.0 ee%
Specific rotation [a]20/D -280.0 to -290.0 deg(C=0.4, CH3CN)
Effect test of HPLC derivatization Effective as labeling agent for DL-1-Phenylethylamine

Data of Reference

ee >99.0%(HPLC)

References

PubChem SID 87563185

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 isomers to Edman Degradation.

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

References

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