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Degradingdehydroabietylisothiocyanate as a chiral derivatizing reagent for enantiomeric separations by capillary electrophoresis.
Electrophoresis. 2006 Sep; 27(17):3428-33.E

Abstract

Abietic acid is a naturally occurring enantiomeric diterpenic acid. Its absolute optical purity and very stable stereochemistry structure makes it an excellent starting material for preparing chiral derivatizing reagents for chromatographic or electrophoretic applications. This paper describes the synthesis and evaluation of a novel chiral derivatization reagent, i.e., degradingdehydroabietylisothiocyanate (DDHAIC) derived from dehydroabietic acid. Its applicability for the enantioseparation of racemic amino acids by CE was demonstrated. DDHAIC reacted readily with amino acids at an elevated temperature (70 degrees C). The resulting derivatives were highly stable and separable by MEKC. Separation of amino acid-DDHAIC diastereomers was achieved with a running buffer consisting of 50 mM Na(2)HPO(4) (pH 9.0), 18 mM SDS, and 25% v/v ACN. Under the conditions selected, diastereomers formed from ten pairs of tested amino acid enantiomers including D/L-Asn, D/L-Met, D/L-Leu, D/L-Phe, D/L-Trp, D/L-Ser, D/L-Val, D/L-Ala, D/L-Thr, and R/S-vigabatrin were well resolved. The resolution values were in the range of 0.95-8.9.

Authors+Show Affiliations

Zhao S
College of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin, China.
Wang H
No affiliation info available
Zhang R
No affiliation info available
Tang L
No affiliation info available
Liu YM
No affiliation info available

MeSH

Amino AcidsElectrophoresis, CapillaryIndicators and ReagentsIsothiocyanatesPhenanthrenesStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16892482

Citation

Zhao, Shulin, et al. "Degradingdehydroabietylisothiocyanate as a Chiral Derivatizing Reagent for Enantiomeric Separations By Capillary Electrophoresis." Electrophoresis, vol. 27, no. 17, 2006, pp. 3428-33.
Zhao S, Wang H, Zhang R, et al. Degradingdehydroabietylisothiocyanate as a chiral derivatizing reagent for enantiomeric separations by capillary electrophoresis. Electrophoresis. 2006;27(17):3428-33.
Zhao, S., Wang, H., Zhang, R., Tang, L., & Liu, Y. M. (2006). Degradingdehydroabietylisothiocyanate as a chiral derivatizing reagent for enantiomeric separations by capillary electrophoresis. Electrophoresis, 27(17), 3428-33.
Zhao S, et al. Degradingdehydroabietylisothiocyanate as a Chiral Derivatizing Reagent for Enantiomeric Separations By Capillary Electrophoresis. Electrophoresis. 2006;27(17):3428-33. PubMed PMID: 16892482.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Degradingdehydroabietylisothiocyanate as a chiral derivatizing reagent for enantiomeric separations by capillary electrophoresis. AU - Zhao,Shulin, AU - Wang,Hengshan, AU - Zhang,Rongcan, AU - Tang,Lidong, AU - Liu,Yi-Ming, PY - 2006/8/8/pubmed PY - 2006/11/14/medline PY - 2006/8/8/entrez SP - 3428 EP - 33 JF - Electrophoresis JO - Electrophoresis VL - 27 IS - 17 N2 - Abietic acid is a naturally occurring enantiomeric diterpenic acid. Its absolute optical purity and very stable stereochemistry structure makes it an excellent starting material for preparing chiral derivatizing reagents for chromatographic or electrophoretic applications. This paper describes the synthesis and evaluation of a novel chiral derivatization reagent, i.e., degradingdehydroabietylisothiocyanate (DDHAIC) derived from dehydroabietic acid. Its applicability for the enantioseparation of racemic amino acids by CE was demonstrated. DDHAIC reacted readily with amino acids at an elevated temperature (70 degrees C). The resulting derivatives were highly stable and separable by MEKC. Separation of amino acid-DDHAIC diastereomers was achieved with a running buffer consisting of 50 mM Na(2)HPO(4) (pH 9.0), 18 mM SDS, and 25% v/v ACN. Under the conditions selected, diastereomers formed from ten pairs of tested amino acid enantiomers including D/L-Asn, D/L-Met, D/L-Leu, D/L-Phe, D/L-Trp, D/L-Ser, D/L-Val, D/L-Ala, D/L-Thr, and R/S-vigabatrin were well resolved. The resolution values were in the range of 0.95-8.9. SN - 0173-0835 UR - https://www.unboundmedicine.com/medline/citation/16892482/Degradingdehydroabietylisothiocyanate_as_a_chiral_derivatizing_reagent_for_enantiomeric_separations_by_capillary_electrophoresis_ L2 - https://doi.org/10.1002/elps.200600008 DB - PRIME DP - Unbound Medicine ER -

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