View PDF Version
 
DOI: 10.1039/A802374C (Paper) Reference Section for: Chem. Commun., 1998, 1759-1760

Enantioselectivity vs. kinetic resolution in antibody catalysis: formation of the (S) product despite preferential binding of the (R) intermediate

(Note: The full text of this document is currently only available in the PDF Version )

Doron Shabat, Ehud Keinan, Doron Shabat, Hagit Shulman, Harel Itzhaky and Jean-Louis Reymond

Abstract

Antibody 14D9, which catalyzes the stereoselective transformation of achiral enol ethers into the corresponding (S)-ketals, resolves a racemic mixture of structurally similar chiral enol ethers by selective conversion of the (R)-enol ether into the (R)-ketal, raising the possibility that the (S) transition state is preferencially stabilized by the antibody despite a better binding of the (R) intermediate.

References

  1. P. G. Schultz and R. A. Lerner, Science, 1995, 269, 1835 CAS; E. Keinan and R. A. Lerner, Isr. J. Chem., 1996, 36, 113 CAS; R. A. Lerner, S. J. Benkovic and P. G. Schultz, Science, 1991, 252, 659 CAS; N. R. Thomas, Nat. Prod. Rep., 1996, 479 RSC.
  2. T. L. Li, R. A. Lerner and K. D. Janda, Acc. Chem. Res., 1997, 30, 115 CrossRef CAS.
  3. J.-P. Charbonnier, B. Golinelli-Pimpaneau, B. Gigant, D. S. Tawfik, R. Chap, D. G. Schindler, S.-H. Kim, B. S. Green, Z. Eshhar and M. Knossow, Science, 1997, 275, 1140 CrossRef CAS; G. J. Wedemayer, P. A. Patten, L. H. Wang, P. G. Schultz and R. C. Stevens, Science, 1997, 276, 1665 CrossRef CAS.
  4. J.-L. Reymond, K. D. Janda and R. A. Lerner, Angew. Chem., Int. Ed. Engl., 1991, 30, 1711 CrossRef; S. C. Sinha, E. Keinan and J.-L. Reymond, Proc. Natl. Acad. Sci. U.S.A., 1993, 90, 11 910 CAS; S. C. Sinha, E. Keinan and J.-L. Reymond, J. Am. Chem. Soc., 1993, 115, 4893 CrossRef CAS; J.-L. Reymond, J.-L. Reber and R. A. Lerner, Angew. Chem., Int. Ed. Engl., 1994, 33, 475 CrossRef; S. C. Sinha and E. Keinan, J. Am. Chem. Soc., 1995, 117, 3653 CrossRef CAS.
  5. D. Shabat, S. C. Sinha, J.-L. Reymond and E. Keinan, Angew. Chem., 1996, 35, 2628 CAS.
  6. D. Shabat, H. Itzaky, J.-L. Reymond and E. Keinan, Nature, 1995, 374, 143 CrossRef CAS.
  7. S. C. Sinha and E. Keinan, Isr. J. Chem., 1996, 36, 185 CAS.
  8. Separation of the enantiomers was carried out using a normal phase chiral column (Chiralcel OD, Chiral Technologies Inc.) with hexane-PriOH (80∶20) at a flow rate of 1 ml min–1; the retention times of (S)-5 and (R)-5 are 9.13 and 12.23 min, respectively.
  9. J. L. Kurz, J. Am. Chem. Soc., 1963, 85, 987 CrossRef CAS; J. Kraut, Science, 1988, 242, 533 CAS; J.-L. Reymond and Y. Chen, Isr. J. Chem., 1996, 36, 199 CAS.
  10. J.-L. Reymond, G. K. Jahangiri, C. Stoudt and R. A. Lerner, J. Am. Chem. Soc., 1993, 115, 3909 CrossRef CAS.
  11. G. K. Jahangiri and J.-L. Reymond, J. Am. Chem. Soc., 1994, 116, 11 264 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.