Synthesis, conformation and biological activity of centrally modified pseudopeptidic analogues of For-Met-Leu-Phe-OMe

Amino Acids

Volumn 33, Issue 3, 2007, Pages 477-487

  Giordano, C ^a   Lucente, G ^a   Masi, A ^a   Paglialunga Paradisi, M ^a   Sansone, A ^a   Spisani, S ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

Author keywords

Thiopeptides; Chemotactic peptides; Conformation; Neutrophils; Pseudopeptides

Indexed keywords

BETA ALANINE; LYSOZYME; PHENYLALANINE; PSEUDOPEPTIDE; SUPEROXIDE; TRIPEPTIDE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMOTAXIS; CONFORMATION; HUMAN; HUMAN CELL; NEUTROPHIL; PRIORITY JOURNAL;

CHEMOTAXIS, LEUKOCYTE; HUMANS; MOLECULAR STRUCTURE; N-FORMYLMETHIONINE LEUCYL-PHENYLALANINE; NEUTROPHILS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES; SOLVENTS; SUPEROXIDES;

EID: 34548324180     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-006-0422-y     Document Type: Article

References (27)

1. 5c). A joint computational and experimental study Org Biomol Chem 1 1980 1988
2. M Aschi A Mollica G Lucente M Paglialunga Paradisi F Mazza 2006 Conformational properties of β-residue-containing oligopeptides in apolar solvent J Mol Struct 785 176 181
3. A Calcagni E Gavuzzo G Lucente F Mazza E Morera M Paglialunga Paradisi D Rossi 2000 Peptides containing the sulfonamide junction. 2. Structure and conformation of Z-Tau-Pro-D-Phe-NhiPr Biopolymers 54 379 387
4. MP Cava MI Levinson 1985 Thionation reactions of Lawesson's reagent Tetrahedron 41 5061 5087
5. AR Dentino PA Raj KK Bhandary ME Wilson MJ Levine 1991 Role of peptide backbone conformation on biological activity of chemotactic peptides J Biol Chem 266 18460 18468
6. C Gennari M Gude D Potenza U Piarulli 1998 Hydrogen bonding donor/acceptor scales in β-sulfonamidopeptides Chem Eur J 4 1924 1931
7. C Giordano G Lucente M Nalli G Pagani Zecchini M Paglialunga Paradisi K Varani S Spisani 2003 Synthesis and activity of HCO-Met-Leu-Phe-OMe analogues containing β-alanine or taurine at the central position Farmaco 58 1121 1130
8. 3- peptides with proteinogenic side chains. Monosubstituted analogues of the chemotactic tripeptide For-Met-Leu-Phe-Ome J Peptide Sci 10 510 523
9. DJ Hill JM Mio RB Prince TS Hughes JS Moore 2001 A field guide to foldamers Chem Rev 101 3893 4011
10. M Hòllosi M Zewdu E Kollàt Z Majer M Kajtàr G Batta K Koevèr P Sàndor 1990 Intramolecular H-bonds and thioamide rotational isomerism in thiopeptides Int J Peptide Res 36 173 181
11. D Krumme H Tschesche 1999 Synthesis and reduction of endothiodipeptides containing malonic acid derivatives Tetrahedron 55 3007 3018
12. G Lajoie JL Kraus 1984 Rapid and efficient method for the N-formylation of C-blocked peptides Peptides 5 653 654
13. Y Le Y Yang Y Cui H Yazawa W Gong C Qiu JM Wang 2002 Receptors for chemotactic formyl peptides as pharmacological targets Int Immunopharmacol 2 1 13
14. H-J Lee Y-S Choi K-B Lee J Park C-J Yoon 2003 Hydrogen bonding abilities of thioamide J Phys Chem A 106 7010 7017
15. Lowik DWPM, Liskamp RMJ (2000) Synthesis of α- and β-substituted aminoethane sulphonamide arginine-glycine mimics. Eur J Org Chem: 1219-1228
16. HL Malech JI Gallin 1987 Neutrophils in human diseases N Engl J Med 317 687 694
17. BK Min H-J Lee YS Choi J Park C-J Yoon J-A Yu 1998 A comparative study on the hydrogen bonding ability of amide and thioamide using near IR spectroscopy J Mol Struct 471 283 288
18. 3,3-aminoacids at the central position Amino Acids 30 453 459
19. G Pagani Zecchini E Morera M Nalli M Paglialunga Paradisi G Lucente S Spisani 2001 Synthesis and activity on human neutrophil functions of fMLF-OMe analogs containing alkyl spacers at the central position Farmaco 56 851 858
20. ER Prossnitz RD Ye 1997 The N-formyl peptide receptor: a model for the study of chemoattractant receptor structure and function Pharmacol Ther 74 73 102
21. RS Rathore 2005 Conformational investigations on analogs of inflammation response inducing chemotactic tripeptide fMLP Biopolymers (Pept Sci) 80 651 664
22. RA Shaw E Kollàt M Hòllosi HH Mantsch 1995 Hydrogen bonding and isomerization in thioamide peptide derivatives Spectrochim Acta Part A 51 1399 1412
23. DB Sherman AF Spatola 1990 Compatibility of thioamides with reverse turn features: synthesis and conformational analysis of two model cyclic pseudopeptides containing thioamides as backbone modifications J Am Chem Soc 112 433 441
24. HJ Showell RJ Freer SH Zigmond E Schiffmann S Aswanikumar B Corcoran EL Becker 1976 The structure-activity relations of synthetic peptides as chemotactic factors and inducers of lysosomal enzyme secretion for neutrophils J Exp Med 143 1154 1169
25. T Sifferlen M Rueping K Gademann B Jaun D Seebach 1999 β-Thiopeptides: synthesis, NMR solution structure, CD spectra, and photochemistry Helv Chim Acta 82 2067 2091
26. 10-helices J Am Chem Soc 124 5222 5230
27. SH Zigmond JG Hirsc 1973 Leukocyte locomotion and chemotaxis. New methods for evaluation and demonstration of cell-derived chemotactic factor J Exp Med 137 387 410