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Titolo:
MODIFIED CHEMOTACTIC PEPTIDES - SYNTHESIS, CONFORMATION, AND ACTIVITYOF HCO-THP-AC(6)C-PHE-OME
Autore:
TORRINI I; ZECCHINI GP; PARADISI MP; LUCENTE G; MASTROPIETRO G; GAVUZZO E; MAZZA F; POCHETTI G; TRANIELLO S; SPISANI S;
Indirizzi:
UNIV ROMA LA SAPIENZA,CNR,DIPARTIMENTO STUDI FARMACEUT,PIAZZALE ALDO MORO 5 I-00185 ROME ITALY UNIV ROMA LA SAPIENZA,CNR,CTR STUDIO CHIM FARMACO I-00185 ROME ITALY G GLACOMELLO CNR,IST STRUTTURIST CHIM I-00016 MONTEROTONDO ITALY UNIV FERRARA,DIPARTIMENTO BIOCHIM & BIOL MOL I-44100 FERRARA ITALY
Titolo Testata:
Biopolymers
fascicolo: 3, volume: 39, anno: 1996,
pagine: 327 - 337
SICI:
0006-3525(1996)39:3<327:MCP-SC>2.0.ZU;2-8
Fonte:
ISI
Lingua:
ENG
Soggetto:
ALPHA,ALPHA-DISUBSTITUTED AMINO-ACIDS; LEU-PHE-OME; BIOLOGICAL-ACTIVITY; 1-AMINOCYCLOHEXANECARBOXYLIC ACID; MODEL PEPTIDES; ROTATING-FRAME; RESIDUES; ANALOGS; CHAIN; MET;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
31
Recensione:
Indirizzi per estratti:
Citazione:
I. Torrini et al., "MODIFIED CHEMOTACTIC PEPTIDES - SYNTHESIS, CONFORMATION, AND ACTIVITYOF HCO-THP-AC(6)C-PHE-OME", Biopolymers, 39(3), 1996, pp. 327-337

Abstract

HCO-Thp-Ac(6)c-Phe-OMe (3) has been synthesized as a new analogue of the prototypical chemotactic agent HCO-Met-Leu-Phe-OMe (fMLP-OMe). Compound 3 contains 4-aminotetrahydrothiopyran-4-carboxylic acid (Thp) and 1-aminocyclohexane-1-carboxylic acid (Ac(6)c) as achiral, conformationally restricted mimics of Met and Leu, respectively. In the crystal,the formyltripeptide adopts an helical conformation at the Thp and Ac(6)c residues, of the type alpha(R) and alpha(L), respectively, whereas the C-terminal phenylalanine is quasi-extended. A system of two consecutive gamma-turns, centered at the first two residues, better explains the nmr data as compared with an alternative beta-turn structure. The conformation of the new analogue 3 is compared with those of two related peptides containing Thp as N-terminal residue. The biological activity of 3 has been determined on human neutrophils and compared to that of the previously studied model [Ac(6)c(2)] fMLP-OMe. While the above analogue is highly active in the superoxide anion production, the new tripeptide 3 is practically unable to elicit any of the tested biological activities. (C) 1996 John Wiley & Sons, Inc.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 22/09/20 alle ore 15:53:05