Synthesis of beta -pyrazinyl-L-alanine (Paa) and of peptide derivatives
Petermann, C; Fauchere, JL
| HERO ID | 4933595 |
|---|---|
| In Press | No |
| Year | 1983 |
| Title | Synthesis of beta -pyrazinyl-L-alanine (Paa) and of peptide derivatives |
| Authors | Petermann, C; Fauchere, JL |
| Journal | Helvetica Chimica Acta |
| Volume | 66 |
| Issue | 5 (1983) |
| Page Numbers | 1513-1518 |
| Abstract | The title compound was prepared via a malonic ester synthesis starting with a-chloromethylpyrazine, and ending, after an asymmetric enzymatic hydrolysis of the racemic N-acetyl- beta -2-pyrazinylalanine to the L-form of the new amino acid. The optical purity was ascertained by super(1)H-NMR analysis at 360 MHz of the diastereoisomeric dipeptides L-pyrazinylalanine-L-leucine and D-pyrazinylalanine-L-leucine. Hydrophobic, steric and electronic parameters for its side chain were also estimated. The new amino acid could be introduced in the place of phenylalanine in the enkephalin-like pentapeptide (D-alanyl super(2), leucine super(5))enkephalin, thus showing good stability towards the classical methods of peptide synthesis. |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | enkephalin; dipeptides; beta -pyrazinyl-L-alanine |