ORGN 729 |
Synthesis of quaternary amino acids bearing an alpha-(2'Z)-fluorovinyl branch: Potential PLP enzyme inactivators
| David B. Berkowitz, Roberto de la Salud-Bea, and Wan Jin Jahng. Department of Chemistry, University of Nebraska, Lincoln, NE 68588-0304 |
| Protected alpha-formyl amino acids, themselves available from the corresponding alpha-vinyl amino acids, are stereoselectively transformed into the (Z)-configured a-(2’-fluoro)vinyl amino acids via a three step sequence. The route employs McCarthy’s reagent, diethyl alpha-fluoro-alpha-(phenylsulfonyl)methyl phosphonate, and goes via the intermediate (E)-fluorovinylsulfones and (E)-fluorovinylstannanes. The latter may either be exploited as novel cross-coupling partners for fluorovinyl branch extension, or be globally deprotected, to provide the title compounds. The potential for inactivation of pyridoxal phosphate (PLP) enzymes with this class of unnatural amino acids will be discussed. 
|
| |
|
Proteins, Peptides, and Amino Acids
8:00 AM-12:00 PM, Thursday, August 26, 2004 Pennsylvania Convention Center -- 201A, Oral
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
|