Synthesis,conformation and biological activity of centrally modified pseudopeptidic analogues of For-Met-Leu-Phe-OMe |
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Authors: | C Giordano G Lucente A Masi M Paglialunga Paradisi A Sansone S Spisani |
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Institution: | (1) Dipartimento di Studi Farmaceutici, Università degli Studi di Roma ‘La Sapienza’, Rome, Italy;(2) Sezione di Roma, Dipartimento di Studi Farmaceutici, Istituto di Chimica Biomolecolare del CNR, Università degli Studi di Roma ‘La Sapienza’, Rome, Italy;(3) Dipartimento di Biochimica e Biologia Molecolare, Università di Ferrara, Ferrara, Italy |
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Abstract: | Summary. For-Met-βAlaψCSNH]-Phe-OMe (3), For-Met-βAlaψCH2NH]-Phe-OMe (5), For-Met-NH-pC6H4-SO2-Phe-OMe (8a), For-Met-NH-mC6H4-SO2-Phe-OMe (8b) and the corresponding N-Boc precursors (2, 4, 7a, b) have been synthesized and their activity towards human neutrophils has been evaluated in comparison with that shown by the
reference tripeptide For-Met-Leu-Phe-OMe (fMLF-OMe). Chemotaxis, lysozyme release and superoxide anion production have been
measured. 1H NMR titration experiments and IR spectra have been discussed in order to ascertain the preferred solution conformation adopted
by the tripeptide 3 with particular reference to the presence of a folded conformation centred at the centrally positioned thionated β-residue. |
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Keywords: | : Chemotactic peptides – Conformation – Neutrophils – Pseudopeptides – β -Thiopeptides |
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