Abstract
The new fMLF analogues 1-4, incorporating chimeric S-proline-methionine residues (namely the homochiral cis-4(S)-methylthio-(S)-proline (10) and the heterochiral trans-4(R)-methylthio-(S)-proline) (17) in place of the native S-methionine, have been prepared; their solution conformation and activity as agonists or antagonists of formylpeptide receptors have been studied. In addition to peptides 1-4, which maintain the Met gamma-thiomethyl-ether function, the analogues Boc-PLF-OMe (18) and For-PLF-OMe (19) devoid, as compared with 1-4, of position 1 side chain, have been synthesized and their activity examined.
MeSH terms
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Cytoplasmic Granules / drug effects
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Cytoplasmic Granules / enzymology
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Humans
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Magnetic Resonance Spectroscopy / methods
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Methionine / chemistry*
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Molecular Conformation
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Muramidase / drug effects
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N-Formylmethionine Leucyl-Phenylalanine* / analogs & derivatives
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N-Formylmethionine Leucyl-Phenylalanine* / chemistry
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N-Formylmethionine Leucyl-Phenylalanine* / pharmacology
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Neutrophils / drug effects
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Neutrophils / enzymology
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Oligopeptides / chemistry*
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Proline / chemistry*
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Stereoisomerism
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Structure-Activity Relationship
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Thiazoles
Substances
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Oligopeptides
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Thiazoles
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trans-4(R)-methylthio-(S)-proline
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N-Formylmethionine Leucyl-Phenylalanine
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Proline
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Methionine
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Muramidase