Home
Resources
Publications
Liquid chromatography/atmospheric Pressure Chemical Ionization Tandem Mass Spectrometry Enantiomeric Separation of Dl-Threo-Methylphenidate, (Ritalin) Using a Macrocyclic Antibiotic as the Chiral Selector

Liquid chromatography/atmospheric Pressure Chemical Ionization Tandem Mass Spectrometry Enantiomeric Separation of Dl-Threo-Methylphenidate, (Ritalin) Using a Macrocyclic Antibiotic as the Chiral Selector

L Ramos, R Bakhtiar, T Majumdar, M Hayes, F Tse

Rapid Commun Mass Spectrom. 1999;13(20):2054-62.

PMID: 10510420

Abstract:

Vancomycin, a macrocyclic antibiotic, is an amphoteric glycopeptide produced by Streptomyces orientalis which has proven to be a viable chiral selector for high performance liquid chromatograph (HPLC) (D. W. Armstrong, Y. Tang, S. Chen, Y. Zhou, C. Bagwill and J-R. Chen, Anal. Chem. (1994; 66: 1473). While it is related to other glycopeptide antibiotics, vancomycin has a number of unique structural features, including 18 stereogenic centers, five aromatic rings, and two side chains one of which is a carbohydrate dimer. Therefore, a vancomycin-based stationary phase appears to be multimodal in that it can be utilized in both normal-phase and reversed-phase liquid chromatography. Consequently, the enantiomeric separation may be operative via several mechanisms, including pi-pi complexation, dipole stacking, inclusion, hydrogen bonding, or combinations of these interactions. LC/MS/MS is a powerful tool for quantitative analysis when evaluated on the basis of speed, specificity, reliability and sensitivity. For these reasons, the present paper explored the feasibility of bonded macrocyclic glycopeptide phases for chiral LC/MS/MS quantitative analysis. Methylphenidate was used as a model compound. A rapid chiral bioanalytical method (<7.5 min) for the determination of the enantiomers of methylphenidate was developed. A lower limit of quantification (LLOQ) of 87 pg/mL was attained for the human plasma assay. This is to our knowledge the first example of enantioselective reversed-phase LC/MS/MS for methylphenidate. The chiral column was relatively cost effective and exhibited excellent performance with no separation deterioration observed after approximately 2500 injections.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP19395405-B	Methylphenidate Related Compound A		19395-40-5	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: