I  U  P  A  C






News & Notices

Organizations & People

Standing Committees

Divisions

Projects

Reports

Publications
..CI
..PAC
..Macro. Symp.

..Books
..Solubility Data

Symposia

AMP

Links of Interest

Search the Site

Home Page

 

Pure Appl. Chem. Vol. 72, No. 3, pp. 347-354, 2000

 

Novel reagents and reactions for drug design*

T. J. Baker, Y. Rew, and M. Goodman**

Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093-0343, USA

Abstract: In this presentation, we cover new results from two of our synthetic endeavors: guanidinylation reagents and novel bridged opioids. In the first part, we describe the applications of the diurethane-triflylguanidines to prepare target bioactive structures including peptides, heterocyclic drugs, and aminoglycoside derivatives. The formation of novel guanidinoglycosides led to a family of effective binders to the RNA recognition element of the HIV-1 Rev protein. In the second part, the syntheses of sulfur and amine-bridged cyclic opioids is described. These analogs exhibit enhanced binding, both in vitro and in vivo. Specifically, H-Tyr-c[D-ValL -Gly-Phe-D/L-AlaL ]-OH (ValL and AlaL denote the lanthionine amino acid ends linked by a monosulfide bridge) is potent and highly d -receptor selective while Tyr-c[(Ng CH3 )-D-A2 bu-Gly-Phe-NHCH2CH2 -] though nonselective is one of the most potent opioids prepared to date. These molecules are representative of our design of novel peptidomimetic opioids.

*Lecture presented at the 5th International IUPAC Symposium on Bioorganic Chemistry (ISBOC-5), Pune, India, 30 January - 4 February, 2000.
**Corresponding author

Back to Contents for access to full text

 


Page last modified 23 June 2000.
Copyright ©2000 International Union of Pure and Applied Chemistry.
Questions or comments about IUPAC, please contact, the Secretariat.
Questions regarding the website, please contact web manager.