Abstract
A new class of chiral stationary phases (CSP) with peptide chiral selectors was prepared by solid-phase synthesis with a tert-butoxycarbonyl-L-amino acid on silica. The type of amino acid that is favorable for this class of CSP is discussed. Using the CSP with the phenylalanine peptide selector, the effect of peptide length on the enantioselectivity was investigated in normal-phase mode. The applicability of the CSP with a phenylalanine peptide to chiral ligand-exchange chromatography was also examined.
References
Muderawan IW, Ong TT, Ng SC (2006) J Sep Sci 29:1849–1871. doi:10.1002/jssc.200500491
Berthod A, Chen X, Kullman JP, Armstrong DW, Gasparrini F, D’Acquarica I, Villani C, Carotti A (2000) Anal Chem 72:1767–1780. doi:10.1021/ac991004t
Yashima E, Yamamoto C, Okamoto Y (1996) J Am Chem Soc 118:4036–4048. doi:10.1021/ja960050x
Danel C, Foulon C, Guelzim A, Park CH, Bonte JP, Vaccher C (2005) Chirality 17:600–607. doi:10.1002/chir.20206
Pirkle WH, Finn JM, Schreiner JL, Hamper BC (1981) J Am Chem Soc 103:3964–3966. doi:10.1021/ja00403a076
Schill G, Wainer IW, Barkan SA (1986) J Chromatogr 365:73–88. doi:10.1016/S0021-9673(01)81544-2
Lämmerhofer M, Lindner W (1996) J Chromatogr A 741:33–48. doi:10.1016/0021-9673(96)00137-9
Dobashi A, Dobashi Y, Kinoshita K, Hara S (1988) Anal Chem 60:1985–1987. doi:10.1021/ac00169a032
Huang J, Chen H, Li T (2006) J Chromatogr A 1113:109–115. doi:10.1016/j.chroma.2006.01.128
Shundo A, Sakurai T, Takafuji M, Nagaoka S, Ihara H (2005) J Chromatogr A 1073:169–174. doi:10.1016/j.chroma.2004.08.062
Chen Y, Yu DH (1993) J App Polym Sci 49:851–861. doi:10.1002/app.1993.070490511
Allenmark SG, Andersson S (1994) J Chromatogr A 666:167–179. doi:10.1016/0021-9673(94)80379-X
Ohyama K, Oyamada K, Kishikawa N, Ohba Y, Wada M, Maki T, Nakashima K, Kuroda N (2008) J Chromatogr A 1208:242–245. doi:10.1016/j.chroma.2008.08.121
Pozdnev VF (1976) Chem Nat Compd 10:782–784
West BD, Preis S, Schroeder CH, Link KP (1961) J Am Chem Soc 83:2676–2679. doi:10.1021/ja01473a020
Kaiser E, Bossinger CD, Colescott RL, Olsen DB (1980) Anal Chim Acta 118:149–151. doi:10.1016/S0003-2670(01)93726-2
Guan-Sajonz H, Guiochon G (1996) J Chromatogr A 743:247–259. doi:10.1016/0021-9673(96)00300-7
Gö M, Hesselink T, Gö N, Scheraga HA (1974) Macromolecule 7:459–467. doi:10.1021/ma60040a013
Mossel E, Formaggio F, Valle G, Crisma M, Toniolo C, Doi M, Ishida T, Broxterman QB, Kamphuis J (1998) Lett Pept Sci 5:223–225. doi:10.1023/A:1008809532026
Harrington WF, Sela M (1958) Biochim Biophys Acta 27:24–41. doi:10.1016/0006-3002(58)90289-0
Davankov VA, Navratil JD, Walton HF (eds) (1988) Ligand exchange chromatography. CRC press, Boca Raton
Acknowledgment
The authors thank Daiso Co., Ltd. (Osaka) for the kind gift of 3-aminopropyl silyl silica gel.
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Ohyama, K., Oyamada, K., Kishikawa, N. et al. Investigation of Novel Peptide Chiral Selectors Prepared by Solid-Phase Synthesis with a tert-Butoxycarbonyl Amino Acid. Chroma 70, 1501–1504 (2009). https://doi.org/10.1365/s10337-009-1345-z
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DOI: https://doi.org/10.1365/s10337-009-1345-z