Screening of a parallel combinatorial library for selectors for chiral chromatography

Analytical Chemistry

Volumn 71, Issue 19, 1999, Pages 4178-4182

  Wang, Yan ^a   Li, Tingyu ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHIRAL CHROMATOGRAPHY; CIRCULAR DICHROISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMOBILIZATION;

EID: 0033215492     PISSN: 00032700     EISSN: None     Source Type: Journal    
DOI: 10.1021/ac9905017     Document Type: Article

References (25)

1. Wu, Y.; Wang, Y.; Yang, A.; Li, T. Anal. Chem. 1999, 71, 1688-1691.
2. Bunin, B. A. The Combinatorial Index; Academic Press: New York, 1998; pp 5-8. See also: Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
3. Bunin, B. A. The Combinatorial Index; Academic Press: New York, 1998; pp 5-8. See also: Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
4. (a) Pirkle, W. H.; Welch, C. J.; Lamm, B. J. Org. Chem. 1992, 57, 3854-3860.
5. (b) Welch, C. J. J. Chromatogr. A 1994, 666, 3-26.
6. (a) Armstrong, D. W. Pittcon '98, New Orleans, March 1-5, 1998.
7. (b) Armstrong, D. W.; Tang, Y.; Chen, S.; Zhou, Y.; Bagwill, C.; Chen, J.-R. Anal. Chem. 1994, 66, 1473-1484.
8. (c) Armstrong, D. W.; Rundlett, K. L.; Chen, J.-R. Chirality 1994, 6, 496-509.
9. Welch, C. J.; Protopopova, M. N.; Bhat, G. Enantiomer 1998, 3, 471-476.
10. Our efforts to synthesize peptides onto silica gel directly have been discouraging. Yang, A.; Gehring, A. P.; Li, T., to be submitted for publication.
11. Lewandowski, K.; Murer, P.; Svec, F.; Frechet, J. M. Chem. Commun. 1998, 2237.
12. All experiments were performed at RT (about 22°C) unless otherwise noted.
13. For the synthesis of this compound and its related chiral studies, see: (a) Pirkle, W. H.; Pochapsky, T. C. J. Am. Chem. Soc. 1986, 108, 352-354. (b) Pirkle, W. H.; Deming, K. C.; Burke, J. A. Chirality 1991, 3, 183-187.
14. For the synthesis of this compound and its related chiral studies, see: (a) Pirkle, W. H.; Pochapsky, T. C. J. Am. Chem. Soc. 1986, 108, 352-354. (b) Pirkle, W. H.; Deming, K. C.; Burke, J. A. Chirality 1991, 3, 183-187.
15. For other examples of peptide libraries in chiral separation, see: (a) Jung, G.; Hofstetter, H.; Feiertag, S.; Stoll, D.; Hofstetter, O.; Wiesmuller, K.-H.; Schurig, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2148-2150. (b) Weingarten, M. D.; Sekanina, K.; Still, W. C. J. Am. Chem. Soc. 1998, 120, 9112-9113. (c) Chiari, M.; Desperati, V.; Manera, E.; Longhi, R. Anal. Chem. 1998, 70, 4967-4973. (d) Murer, P.; Lewandowski, K.; Svec, F.; Frechet, J. M. J. Anal. Chem. 1999, 71, 1278-1284. See also ref 5.
16. For other examples of peptide libraries in chiral separation, see: (a) Jung, G.; Hofstetter, H.; Feiertag, S.; Stoll, D.; Hofstetter, O.; Wiesmuller, K.-H.; Schurig, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2148-2150. (b) Weingarten, M. D.; Sekanina, K.; Still, W. C. J. Am. Chem. Soc. 1998, 120, 9112-9113. (c) Chiari, M.; Desperati, V.; Manera, E.; Longhi, R. Anal. Chem. 1998, 70, 4967-4973. (d) Murer, P.; Lewandowski, K.; Svec, F.; Frechet, J. M. J. Anal. Chem. 1999, 71, 1278-1284. See also ref 5.
17. For other examples of peptide libraries in chiral separation, see: (a) Jung, G.; Hofstetter, H.; Feiertag, S.; Stoll, D.; Hofstetter, O.; Wiesmuller, K.-H.; Schurig, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2148-2150. (b) Weingarten, M. D.; Sekanina, K.; Still, W. C. J. Am. Chem. Soc. 1998, 120, 9112-9113. (c) Chiari, M.; Desperati, V.; Manera, E.; Longhi, R. Anal. Chem. 1998, 70, 4967-4973. (d) Murer, P.; Lewandowski, K.; Svec, F.; Frechet, J. M. J. Anal. Chem. 1999, 71, 1278-1284. See also ref 5.
18. For other examples of peptide libraries in chiral separation, see: (a) Jung, G.; Hofstetter, H.; Feiertag, S.; Stoll, D.; Hofstetter, O.; Wiesmuller, K.-H.; Schurig, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2148-2150. (b) Weingarten, M. D.; Sekanina, K.; Still, W. C. J. Am. Chem. Soc. 1998, 120, 9112-9113. (c) Chiari, M.; Desperati, V.; Manera, E.; Longhi, R. Anal. Chem. 1998, 70, 4967-4973. (d) Murer, P.; Lewandowski, K.; Svec, F.; Frechet, J. M. J. Anal. Chem. 1999, 71, 1278-1284. See also ref 5.
19. The Hi-top system, Polyfiltronics, 100 Weymouth Street, Rockland, MA 02370.
20. Poole, C. F.; Poole, S. K. Chromatography today; Elsevier: New York, 1991; pp 350-353.
21. 0 was measured with 1,3,5-tri-tert-butylbenzene as the void volume marker according to Pirkle, W. H.; Welch, C. J. J. Liq. Chromatogr. A 1991, 14, 1-8.
22. R-1 contains about 4% S-1, S-1 contains about 4% R-1. See ref 1.
23. This yield is calculated on the basis of the manufacturer's certification of the AmPS resin. 110% yield indicates that the actual surface amino concentration is higher than manufacturer's suggested value. Therefore, this coupling yield may not reflect accurately the efficiency of the coupling reaction. However, the subsequent coupling of Fmoc-Leu to Abu-AmPS, in which the Abu amount is determined accurately by the Fmoc cleavage method (see ref 16), should be a very reliable measurement of the quality of the coupling reaction. Similar argument could be made concerning the AmTG resin.
24. Method 12: Estimation of level of first residue. NovaBiochem Catalog & Peptide Synthesis Handbook; Nova Biochem: San Diego, CA, 1999; p S43. See also Experimental Section.
25. Pancoska, P.; Bitto, E.; Janota, V.; Keiderling, T. A. In Vibrational Optical Activity: From Fundamentals to Biological Applications; The Faraday Division of the Royal Society of Chemistry: London, 1994; pp 287-311.