Solid-phase synthesis of chemotactic peptides using α-azido acids

Journal of Peptide Science

Volumn 6, Issue 7, 2000, Pages 314-320

  Tornøe, Christian W ^a   Sengeløv, Henrik ^b   Meldal, Morten ^a  

^a CARLSBERG LABORATORY   (Denmark)

^b University of Copenhagen   (Denmark)

Author keywords

, disubstituted; Azido acid; Chemotactic peptide; fMLP; Neutrophil; Solid phase

Indexed keywords

ACID; CHEMOTACTIC PEPTIDE; FORMIC ACID; GLYCINE DERIVATIVE;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARTICLE; CHEMICAL MODIFICATION; NEUTROPHIL; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; SOLID;

AMINO ACID SEQUENCE; AMINO ACIDS; AZIDES; CALCIUM; CHEMOTACTIC FACTORS; DRUG EVALUATION, PRECLINICAL; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; N-FORMYLMETHIONINE LEUCYL-PHENYLALANINE; NEUTROPHILS; OLIGOPEPTIDES; RECEPTORS, FORMYL PEPTIDE; RECEPTORS, IMMUNOLOGIC; RECEPTORS, PEPTIDE;

EID: 0033912727     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-1387(200007)6:7<314::AID-PSC255>3.0.CO;2-E     Document Type: Article

References (16)

1. Becker EL, Freer RJ, Toniolo C, Balaram P. The specificity of the chemotactic formyl peptide receptor of rabbit neutrophils. In Membrane Receptors and Cellular Regulation, Czech MP, Kahn CR (eds). Alan R. Liss: New York, 1985; 129-134.
2. Toniolo C, Formaggio F, Crisma M, Valle G, Boesten WHJ, Schoemaker HE, Kamphuis J, Temussi PA, Becker EL, Precigoux G. Bioactive and model peptides characterized by the helicogenic (xMe)Phe residue. Tetrahedron 1993; 49: 3641-3653.
3. Torrini I, Zecchini GP, Paradisi MP, Lucente G, Gavuzzo E, Mazza F, Pochetti G, Spisani S, Giuliani AL. Synthesis and properties of chemotactic peptide analogs. II. HCO-Met-Leu-Phe-OMe analogs containing cyclic αα-disubstituted amino acids as Met and Phe mimicking residues. Int. J. Pept. Prot. Res. 1991; 38: 495-504.
4. α,α-dialkylated glycine at position 2. Pept. Res. 1989; 2: 275-281.
5. Prasad S, Rao RB, Bergstrand H, Lundquist B, Becker EL, Balaram P. Conformation-activity correlations for chemotactic tripeptide analogs incorporating dialkyl residues with linear and cyclic alkyl side chains at position 2. Int. J. Pept. Prot. Res. 1996; 48: 312-318.
6. Meldal M, Juliano MA, Jansson AM. Azido acids in a novel method of solid-phase peptide synthesis. Tetrahedron Lett. 1997; 38: 2531-2534.
7. Kent SBH. Chemical synthesis of peptides and proteins. Ann. Rev. Biochem. 1988; 57: 957-989.
8. Christensen MK, Meldal M, Bock K. Synthesis of mannose 6-phosphate-containing disaccharide threonine building blocks and their use In solid-phase glycopeptide synthesis. J. Chem. Soc. Perkin Trans. 1 1993; 13: 1453-1460.
9. Meldal M. PEGA: a flow stable polyethylene glycol dimethyl acrylamide copolymer for solid phase synthesis. Tetrahedron Lett. 1992; 33: 3077-3080.
10. Knorr R, Trzeciak A, Bannwarth W, Gillessen D. New coupling reagents in peptide chemistry. Tetrahedron Lett. 1989; 30: 1927-1930.
11. Blankemeyer-Menge B, Nimtz M, Frank R. An efficient method for anchoring Fmoc-amino acids to hydroxyl-functionalised solid supports. Tetrahedron Lett. 1990; 31: 1701-1704.
12. Belleau B, Malek G. A new convenient reagent for peptide syntheses. J. Am. Chem. Soc. 1968; 90: 1651-1652.
13. Sengelov H, Nielsen MH, Borregaard N. Separation of human neutrophil plasma membrane from intracellular vesicles containing alkaline phosphatase and NADPH oxidase activity by free flow electrophoresis. J. Biol. Chem. 1992; 267: 14912-14917.
14. Sengelov H. Secretory vesicles of human neutrophils. Eur. J. Haematol. 1996; 58: 1-24.
15. Carpino LA. 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive. J. Am. Chem. Soc. 1993; 115: 4397-4398.
16. Dentino AR, Raj PA, Bhandary KK, Wilson ME, Levine MJ. Role of peptide backbone conformation on biological activity of chemotactic peptides. J. Biol. Chem. 1991; 266: 18460-18468.