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Enantiomeric separation of D,L-tryptophan and D,L-kynurenine by HPLC using pre-column fluorescence derivatization with R(-)-DBD-PyNCS.
Biomed Chromatogr. 2011 Jul; 25(7):743-7.BC

Abstract

The enantiomeric separation of D,L-tryptophan (Trp) and D,L-kynurenine (KYN) was investigated by high-performance liquid chromatography using pre-column fluorescence derivatization with a chiral fluorescent labeling reagent, R(-)-4-(3-isothiocyanatopyrrolidin-1-yl)-7- (N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole [R(-)-DBD-PyNCS]. Using an octadecylsilica column, namely, an Inertsil ODS-3 column (250 x 2.0 mm; i.d., 3 μm), four fluorescence peaks of D- and L-Trp as well as D- and L-KYN derivatized with R(-)-DBD-PyNCS were clearly observed, and their chemical structures were confirmed by HPLC-time-of-flight-mass spectrometry. Simultaneous separation was achieved under the mobile phase condition of 1.5% acetic acid in H₂O-CH₃CN (60:40), and the separation factors of D,L-Trp and D,L-KYN derivatized with R(-)-DBD-PyNCS were 1.22 and 1.19, respectively. Fluorescence detection was carried out by setting the emission wavelength at 565 nm, and the excitation wavelength at 440 nm, and the detection limits were approximately 0.3-0.5 pmol (signal-to-noise ratio of 3).

Authors+Show Affiliations

Department of Analytical Chemistry, Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi-shi, Chiba 274-8510, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

21656531

Citation

Iizuka, Hideaki, et al. "Enantiomeric Separation of D,L-tryptophan and D,L-kynurenine By HPLC Using Pre-column Fluorescence Derivatization With R(-)-DBD-PyNCS." Biomedical Chromatography : BMC, vol. 25, no. 7, 2011, pp. 743-7.
Iizuka H, Hirasa Y, Kubo K, et al. Enantiomeric separation of D,L-tryptophan and D,L-kynurenine by HPLC using pre-column fluorescence derivatization with R(-)-DBD-PyNCS. Biomed Chromatogr. 2011;25(7):743-7.
Iizuka, H., Hirasa, Y., Kubo, K., Ishii, K., Toyo'oka, T., & Fukushima, T. (2011). Enantiomeric separation of D,L-tryptophan and D,L-kynurenine by HPLC using pre-column fluorescence derivatization with R(-)-DBD-PyNCS. Biomedical Chromatography : BMC, 25(7), 743-7. https://doi.org/10.1002/bmc.1525
Iizuka H, et al. Enantiomeric Separation of D,L-tryptophan and D,L-kynurenine By HPLC Using Pre-column Fluorescence Derivatization With R(-)-DBD-PyNCS. Biomed Chromatogr. 2011;25(7):743-7. PubMed PMID: 21656531.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantiomeric separation of D,L-tryptophan and D,L-kynurenine by HPLC using pre-column fluorescence derivatization with R(-)-DBD-PyNCS. AU - Iizuka,Hideaki, AU - Hirasa,Yasushi, AU - Kubo,Kazumi, AU - Ishii,Kana, AU - Toyo'oka,Toshimasa, AU - Fukushima,Takeshi, Y1 - 2010/10/29/ PY - 2010/03/26/received PY - 2010/07/16/revised PY - 2010/08/09/accepted PY - 2011/6/10/entrez PY - 2011/6/10/pubmed PY - 2011/10/8/medline SP - 743 EP - 7 JF - Biomedical chromatography : BMC JO - Biomed Chromatogr VL - 25 IS - 7 N2 - The enantiomeric separation of D,L-tryptophan (Trp) and D,L-kynurenine (KYN) was investigated by high-performance liquid chromatography using pre-column fluorescence derivatization with a chiral fluorescent labeling reagent, R(-)-4-(3-isothiocyanatopyrrolidin-1-yl)-7- (N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole [R(-)-DBD-PyNCS]. Using an octadecylsilica column, namely, an Inertsil ODS-3 column (250 x 2.0 mm; i.d., 3 μm), four fluorescence peaks of D- and L-Trp as well as D- and L-KYN derivatized with R(-)-DBD-PyNCS were clearly observed, and their chemical structures were confirmed by HPLC-time-of-flight-mass spectrometry. Simultaneous separation was achieved under the mobile phase condition of 1.5% acetic acid in H₂O-CH₃CN (60:40), and the separation factors of D,L-Trp and D,L-KYN derivatized with R(-)-DBD-PyNCS were 1.22 and 1.19, respectively. Fluorescence detection was carried out by setting the emission wavelength at 565 nm, and the excitation wavelength at 440 nm, and the detection limits were approximately 0.3-0.5 pmol (signal-to-noise ratio of 3). SN - 1099-0801 UR - https://www.unboundmedicine.com/medline/citation/21656531/Enantiomeric_separation_of_DL_tryptophan_and_DL_kynurenine_by_HPLC_using_pre_column_fluorescence_derivatization_with_R____DBD_PyNCS_ L2 - https://doi.org/10.1002/bmc.1525 DB - PRIME DP - Unbound Medicine ER -