Purification of high-throughput organic synthesis libraries by counter-current chromatography.

Experiments were performed to evaluate whether counter-current chromatography (CCC) could function as an alternative purification method to reversed-phase high-performance liquid chromatography (RP-HPLC) and normal-phase supercritical fluid chromatography (SFC). RP-HPLC and SFC are the routine methods currently used in our high-throughput purification (HTP) facility for the purification of high-throughput organic synthesis (HTOS) libraries and medicinal chemistry reaction mixtures. Pre-equilibration of the solvent mixture layers was not mandatory for effective chromatography when hexanes-ethyl acetate-methanol-water (HEMW) solvent mixtures were used. Key to the use of CCC for high-throughput applications is the ability to effectively select a solvent system appropriate to each library member. Pilot-scale CCC elution time was used to estimate a starting solvent ratio and RP-HPLC retention time was then used to adjust solvent ratios within a particular library. It was also found that dimethyl sulfoxide (DMSO) and DMSO-methanol were suitable as sample injection solvents when using the HEMW solvent systems.

[1]  G. Pauli,et al.  Performance characteristics of countercurrent separation in analysis of natural products of agricultural significance. , 2008, Journal of agricultural and food chemistry.

[2]  Li Di,et al.  Pharmaceutical profiling method for lipophilicity and integrity using liquid chromatography-mass spectrometry. , 2003, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[3]  R. Bowman,et al.  Countercurrent Chromatography with Flow-Through Coil Planet Centrifuge , 1971, Science.

[4]  Yoichiro Ito,et al.  Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[5]  G. Pauli,et al.  G.U.E.S.S.—A Generally Useful Estimate of Solvent Systems for CCC , 2005 .

[6]  F. Lombardo,et al.  ElogPoct: a tool for lipophilicity determination in drug discovery. , 2000, Journal of medicinal chemistry.

[7]  W. Conway Counter-current chromatography , 1991 .

[8]  A. Berthod,et al.  Using the Liquid Nature of the Stationary Phase: The Elution‐Extrusion Method , 2005 .

[9]  S. Markey,et al.  Preparative separation of polar unstable compounds (catecholamines) from a synthetic mixture by high-speed counter-current chromatography , 1986 .

[10]  Hogeboom Gh,et al.  Separation and characterization of some penicillins by the method of counter-current distribution. , 1947 .

[11]  L. Craig,et al.  Automatic Countercurrent Distribution Equipment , 1951 .

[12]  Jill E Hochlowski,et al.  Comparison of preparative HPLC/MS and preparative SFC techniques for the high-throughput purification of compound libraries. , 2004, Journal of combinatorial chemistry.

[13]  G. Pauli,et al.  Extra‐Column Volume in CCC , 2005 .

[14]  G. Pauli,et al.  Countercurrent separation of natural products. , 2008, Journal of natural products.

[15]  Feiyan Liu,et al.  Multi-channel counter-current chromatography for high-throughput fractionation of natural products for drug discovery. , 2008, Journal of chromatography. A.

[16]  M. Knight,et al.  Rapid purification of synthetic bombesin by countercurrent chromatography on the multi-layer coil planet centrifuge , 1985 .

[17]  R. Bowman,et al.  Countercurrent Chromatography: Liquid-Liquid Partition Chromatography without Solid Support , 1970, Science.

[18]  John Isbell,et al.  Changing requirements of purification as drug discovery programs evolve from hit discovery. , 2008, Journal of combinatorial chemistry.

[19]  Y. Ito Origin and Evolution of the Coil Planet Centrifuge: A Personal Reflection of My 40 Years of CCC Research and Development , 2005 .

[20]  R. S. Silva,et al.  Applications of counter-current chromatography in organic synthesis purification of heterocyclic derivatives of lapachol. , 2007, Journal of chromatography. A.

[21]  G. G. Stokes "J." , 1890, The New Yale Book of Quotations.

[22]  Yuanjiang Pan,et al.  Recent Progress in Countercurrent Chromatography , 2007 .

[23]  A. Berthod,et al.  Rapid screening of bioactive components from Zingiber cassumunar using elution-extrusion counter-current chromatography. , 2008, Journal of chromatography. A.