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Titolo:
MODIFIED CHEMOTACTIC PEPTIDES - SYNTHESIS, CONFORMATION, AND BIOLOGICAL-ACTIVITY OF FOR-THP-LEU-DELTA(Z)PHE-OME
Autore:
TORRINI I; ZECCHINI GP; PARADISI MP; LUCENTE G; GAVUZZO E; MAZZA F; POCHETTI G; TRANIELLO S; SPISANI S; CERICHELLI G;
Indirizzi:
UNIV ROMA LA SAPIENZA,CNR,DIPARTIMENTO STUDI FARMACEUT I-00185 ROME ITALY UNIV ROMA LA SAPIENZA,CNR,CTR STUDIO CHIM FARMACO I-00185 ROME ITALY UNIV FERRARA,IST CHIM BIOL I-44100 FERRARA ITALY UNIV ROMA LA SAPIENZA,CNR,CTR STUDIO MECCANISMI REAZ I-00185 ROME ITALY CNR,IST STRUTTURIST CHIM MONTEROTONDO ITALY
Titolo Testata:
Biopolymers
fascicolo: 10, volume: 34, anno: 1994,
pagine: 1291 - 1302
SICI:
0006-3525(1994)34:10<1291:MCP-SC>2.0.ZU;2-2
Fonte:
ISI
Lingua:
ENG
Soggetto:
BETA-TURN CONFORMATIONS; PHE-OME; CRYSTAL; PROTEINS; ANALOGS; MET; NEUTROPHILS; RESIDUES; DESIGN;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
30
Recensione:
Indirizzi per estratti:
Citazione:
I. Torrini et al., "MODIFIED CHEMOTACTIC PEPTIDES - SYNTHESIS, CONFORMATION, AND BIOLOGICAL-ACTIVITY OF FOR-THP-LEU-DELTA(Z)PHE-OME", Biopolymers, 34(10), 1994, pp. 1291-1302

Abstract

For-Thp-Leu-Delta(2)Phe-OMe (2), an analogue of the chemotactic tripeptide For-Met-Leu-Phe-OMe, containing 4-aminotetrahydrothiopyran-4-carboxylic acid (Thp) and (2)-2,3-didehydrophenylalanine (Delta(2)Phe) asachiral, conformationally restricted mimics of Met and Phe, respectively, has been synthesized. In the crystal the new formyltripeptide adopts a type I beta-turn conformation stabilized by a weak H bond between the formylic oxygen and the Delta(2)Phe NH. H-1-nmr analysis based on NH solvent accessibility and nuclear Overhauser effect experiments suggests that the beta-turn is not preferred in CDCl3 solution where a gamma-turn, centered at the Thp residue, prevails. The biological activity of 2 has been determined on human neutrophils and compared to that of previously studied analogues. The tripeptide 2 is practically unable to elicit superoxide anion production and lysozyme release, while slight, but not statistically significant activity was induced in chemotaxis. The role of the orientation of the aromatic ring with respect to the backbone adjacent atoms is discussed. (C) 1994 John Wiley and Sons, Inc.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 23/09/20 alle ore 09:03:38