| Autor: |
Gispen, W.H., Schaaper, W.M.M.., Adan, R.A.H., Posthuma, T.A., Oosterom, J., Meloen, R.H. |
| Jazyk: |
angličtina |
| Rok vydání: |
1998 |
| Předmět: |
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| Zdroj: |
Letters in peptide science, 5(2-3), 205. ESCOM Science Publishers |
| ISSN: |
0929-5666 |
| Popis: |
Cyclic lactam analogs of -melanocyte stimulating hormone (-MSH) have been shown to be potent agonists in the frog skin bioassay [Al-Obeidi, F. et al., J. Med. Chem., 32 (1989) 2555], demonstrating melanocortin-1 (MC1) receptor activity. We synthesized cyclic -MSH(1-13) and -MSH(4-10) lactam analogs. The peptides were synthesized using Fmoc chemistry. We improved the cyclization procedure: side chains of Asp5 and Lys10 from the deprotected peptide were coupled in DMF to form a cyclic lactam, using an excess of PyBOP reagent and DIEA as a base. The cyclization reaction was completed within 1 h and was almost quantitative. We also synthesized an -MSH analog cyclized via a disulphide bridge. The peptides were tested for their selectivity for the rat MC4 receptor. Cyclization and substitutions at position 7 dramatically influenced the selectivity for the rMC4 receptor. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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