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The Importance of the Methionine Configuration in for-Met-Leu-Phe-OMe Biological Activities

✍ Scribed by Susanna Spisani; Giorgio Cavicchioni

Book ID
102564991
Publisher
Elsevier Science
Year
2000
Tongue
English
Weight
64 KB
Volume
28
Category
Article
ISSN
0045-2068

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✦ Synopsis

for-D-Met-L-Leu-L-Phe-OMe was synthesized in order to understand the importance of the methionine configuration on human neutrophil biological activity. Our results show that both chemotactic response and lysozyme release are lower than those of the parent fMLP-OMe, indicating that the specific receptor pocket possesses a well-located, restricted positive area that does not completely face the D-Met residue. The triggering of superoxide anion production does not seem to be sensitive to this variation of the configuration.

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## Abstract The α/β^3^‐mixed tripeptides R‐CO‐β^3^‐HMet‐Leu‐Phe‐OMe (**1a**,**b**), R‐CO‐Met‐β^3^‐HLeu‐Phe‐OMe (**2a**,**b**) and R‐CO‐Met‐Leu‐β^3^‐HPhe‐OMe (**3a**,**b**) (**a**, R = __tert__‐butyloxy‐; **b**, R = H−), analogues of the potent chemoattractant For‐Met‐Leu‐Phe‐OMe, have been synthesi