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Asymmetric Synthesis of b , g -Substituted Glutamic Acids

Asymmetric Synthesis of b , g -Substituted Glutamic Acids. Hruby, V. J., and Guoxia Han Department of Chemistry University of Arizona. Introduction. The Importance of Glutamic Acid: a -MSH: Ac-Ser-Tyr-Ser-Met- Glu 5 -His-Phe-Arg-Trp-Gly-Lys- Pro-Val-NH 2

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Asymmetric Synthesis of b , g -Substituted Glutamic Acids

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  1. Asymmetric Synthesis of b,g-Substituted Glutamic Acids Hruby, V. J., and Guoxia Han Department of Chemistry University of Arizona

  2. Introduction The Importance of Glutamic Acid: a-MSH: Ac-Ser-Tyr-Ser-Met-Glu5-His-Phe-Arg-Trp-Gly-Lys- Pro-Val-NH2 SRIF: Ser-Ala-Asn-Ser-Asn-Pro-Ala-Met-Ala-Pro-Arg- Glu12-Arg-Lys-Ala-Gly-Cys-Lys-Asn-Phe-Phe-Trp- Lys-Thr-Phe-Thr-Ser-Cys-OH Why Side Chain Substitution? Constrained amino acids Constrained peptides Receptor selective and potent ligands

  3. Retrosynthetic Pathway A

  4. Retrosynthetic Route B

  5. Retrosynthetic Route C

  6. Recent Work

  7. Just in…

  8. Future Plan

  9. Acknowledgements Dr. Victor J. Hruby Dr. Jon Rainier Dr. Koert Hans-Dieter Arndt NIH and USPHS ACS Medicinal Division Contact Email and Web: hruby@u.arizona.edu http://www.chem.arizona.edu ghan@u.arizona.edu

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