Ketomethylenebestatin: synthesis and aminopeptidase inhibition
Herranz, R; Castro-Pichel, J; García-López, MT; Gómez-Monterrey, I; Pérez, C; Vinuesa, S
| HERO ID | 4923736 |
|---|---|
| In Press | No |
| Year | 1993 |
| Title | Ketomethylenebestatin: synthesis and aminopeptidase inhibition |
| Authors | Herranz, R; Castro-Pichel, J; García-López, MT; Gómez-Monterrey, I; Pérez, C; Vinuesa, S |
| Journal | Archiv der Pharmazie |
| Volume | 326 |
| Issue | 7 |
| Page Numbers | 395-398 |
| Abstract | The synthesis of (6R,5S,2RS)-6-amino-5-hydroxy-2-isobutyl-4-oxo-7- phenylheptanoic acid (9), a carbaanalogue of the aminopeptidase (AP) inhibitor bestatin (1) is described. This synthesis was carried out by a malonic ester alkylation with the suitably protected halomethyl ketone of (2S,3R)-AHPBA*), followed by a second alkylation with isobutyl bromide of the resulting 4-ketodiester, and subsequent decarboxylation and deprotection. The inhibitory potencies of the 1:1 diastereomeric mixture 9 against AP-B, AP-M and Leu-AP were approximately 10-fold lower than those of bestatin. |
| Doi | 10.1002/ardp.19933260705 |
| Pmid | 8357301 |
| Wosid | WOS:A1993LP44300004 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |