Advertisement

Chiral effects of alkyl-substituted derivatives of N,O-bismethacryloyl ethanolamine on the performance of one monomer molecularly imprinted polymers (OMNiMIPs)

  • Jason LeJeune
  • David A. SpivakEmail author
Original Paper

Abstract

New monomers were synthesized and evaluated for their molecular imprinting performance by a recently discovered methodology referred to as one monomer molecularly imprinted polymers (OMNiMIPs). The structural design of the new monomers was based on a lead compound methacrylamidoethyl methacrylate (1) used for the synthesis of OMNiMIP1, and introduced alkyl groups of various sizes at the α-amino position of the lead compound. Enantioselectivity, determined by liquid chromatography, was used to compare the performance of the imprinted polymers. Methyl substitution provided crosslinker 5 (2-methacrylamidopropyl methacrylate), which upon imprint polymerization afforded OMNiMIP5 with approximately the same enantioselectivity (α = 3.8) as OMNiMP1 (α = 3.7) made with the lead compound (1). The other two monomers (6 and 7) with larger alkyl substitutions (isopropyl and sec-butyl respectively) resulted in OMNiMIPs with low selectivity values (α = 1.0 and 1.2 respectively). Last, a strong influence of diastereomeric complexes on OMNiMIP5 selectivity was determined, with L/L and D/D monomer/template pairs giving α values of 3.6–3.8, while L/D and D/L monomer/template pairs had α values of 2.3–2.4. There is no intrinsic enantioselectivity seen for the OMNiMIP5 control polymer made without template at all, giving an α value of 1.03.

Keywords

Molecular imprinting Resolution OMNiMIPs Crosslinkers Enantioselectivity Chromatography 

Notes

Acknowledgements

We would like to thank Alan Bussard for assistance with the porosimetry measurements. D.A.S. wishes to thank the National Science Foundation for CAREER Program award CHE-0134290.

Supplementary material

216_2007_1364_MOESM1_ESM.doc (1.9 mb)
Supplementary Material (DOC 1.89 Mb)

References

  1. 1.
    Alexander C, Andersson HS, Andersson LI, Ansell RJ, Kirsch N, Nicholls IA, O’Mahony J, Whitcombe M (2006) J Mol Recognit 19:106–180CrossRefGoogle Scholar
  2. 2.
    Mosbach K (2006) Sci Am 295:87–91CrossRefGoogle Scholar
  3. 3.
    Yan M, Ramstrom O (2005) Molecularly imprinted materials: science and technology. Marcel Dekker, New York, pp 1–734Google Scholar
  4. 4.
    Zimmerman SC, Lemcoff MG (2004) Chem Commun 5–17Google Scholar
  5. 5.
    Marty JD, Mauzac M (2005) Adv Polym Sci 172:1–35Google Scholar
  6. 6.
    Spivak DA, Shea KJ (1999) J Org Chem 64:4627–4634CrossRefGoogle Scholar
  7. 7.
    Shea KJ, Stoddard GJ, Shavelle DM, Wakui F, Choate RM (1990) Macromolecules 23:4497–507CrossRefGoogle Scholar
  8. 8.
    Spivak DA, Sibrian-Vazquez M (2002) Bioseparation 10:331–336CrossRefGoogle Scholar
  9. 9.
    Sibrian-Vazquez M, C Spivak DA (2003) Macromolecules 36:5105–5113CrossRefGoogle Scholar
  10. 10.
    Sibrian-Vazquez M, Spivak DA (2004) J Polym Sci Part A Polym Chem 42:3668–3675CrossRefGoogle Scholar
  11. 11.
    Sibrian-Vazquez M, Spivak DA (2003) J Org Chem 68:9604–9611CrossRefGoogle Scholar
  12. 12.
    Sibrian-Vazquez M, Spivak DA (2004) J Am Chem Soc 126:7827–7833CrossRefGoogle Scholar
  13. 13.
    Simon R, Houck S, Spivak DA (2005) Anal Chim Acta 542:104–110CrossRefGoogle Scholar
  14. 14.
    Chiacchio U, Corsaro A, Gambera G, Rescifina A, Piperno A, Romeo R, Romeo G (2002) Tetrahedron Asymmetry 13:1915CrossRefGoogle Scholar
  15. 15.
    Bailey TR, Dickman DA, Meyers AI (1985) J Am Chem Soc 107:7974CrossRefGoogle Scholar
  16. 16.
    Yamazaki N, Nakahama S, Hirao A, Itsuno S (1983) J Chem Soc Perkin Trans I 8:1673Google Scholar
  17. 17.
    Gavioli E, Maier NM, Haupt K, Mosbach K, Linder W (2005) Anal Chem 77:5009–5018CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2007

Authors and Affiliations

  1. 1.Chemistry DepartmentLouisiana State UniversityBaton RougeUSA

Personalised recommendations