Premium
Solid‐phase Synthesis of Chemotactic Peptides Using α‐Azido Acids
Author(s) -
Tornøe Christian W.,
Sengeløv Henrik,
Meldal Morten
Publication year - 2000
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/1099-1387(200007)6:7<314::aid-psc255>3.0.co;2-e
Subject(s) - chemotaxis , solid phase synthesis , chemistry , peptide , peptide synthesis , amino acid , biological activity , biochemistry , stereochemistry , combinatorial chemistry , in vitro , receptor
Erratum has been published for this article in Journal of Peptide Science 6 (10) 2000, 497–540. Four chemotactic peptides, For‐Met‐Xxx‐Phe‐OMe, with an α,α‐disubstituted amino acid at position 2 have been synthesized by the azido acid method [Meldal M, Juliano MA, Jansson AM. 1997. Azido acids in a novel method of solid‐phase peptide synthesis. Tetrahedron Lett. 38 : 2531–2534] on solid‐phase, and were tested for biological activity. Dipropylglycine in the central position (Xxx) was found to be as active as the natural chemotactic peptide for chemotactic activity toward human neutrophils. Higher yields were obtained than previously reported solution‐phase syntheses of chemotactic peptides, and EEDQ was used successfully for the difficult solid‐phase formylation of amino groups. Copyright © 2000 European Peptide Society and John Wiley & Sons, Ltd.