(R)-(-)-NBD-Py-NCS [=(R)-(-)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7-nitro-2,1,3-benzoxadiazole] [HPLC Labeling Reagent for e.e. Determination]

The compound 1 is an HPLC fluorescence labeling reagent for optical purity determination. This compound easily reacts with amino groups, which are directly linked to an asymmetric carbon atom, and produces diastereomers of thiourea. 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 488 nm and 590 nm, respectively.
Since both (R)- and (S)-isomers of the derivatization reagents are commercially available on the market, it is possible to change the 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 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 °C 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.

TCI Products Pamphlet
HPLC Labeling Reagents ( PDF 10MB )