title: The geranyl-modified tryptophan residue is crucial for ComXRO-E-2 pheromone biological activity.
abstract: The ComX pheromone is an isoprenoidal oligopeptide containing a modified tryptophan residue, which stimulates natural genetic competence in gram-positive bacteria, Bacillus. We have reported the structure of the ComX(RO-E-2) pheromone, which is produced by the RO-E-2 strain of Bacillus subtilis. ComX(RO-E-2) analogs with substituted amino acids and isoprenoid modified tryptophan residues (e.g., prenyl, geranyl, and farnesyl), were synthesized and examined for biological activity. These results indicate that Phe-Trp(∗)(Ger)-NH(2) is the minimum pharmacophore of the ComX(RO-E-2) pheromone. Furthermore, the length of the isoprenoid moiety (i.e., modification style), and the presence of double bonds, are crucial for biological activity. The modification style of the ComX pheromone is more important than the peptide sequence with respect to biological activity.
authors.affiliation: Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan.
authors.forename: Fumitada
authors.initials: F
authors.lastname: Tsuji
authors.forename: Ko
authors.initials: K
authors.lastname: Kobayashi
authors.forename: Masahiro
authors.initials: M
authors.lastname: Okada
authors.forename: Hisao
authors.initials: H
authors.lastname: Yamaguchi
authors.forename: Makoto
authors.initials: M
authors.lastname: Ojika
authors.forename: Youji
authors.initials: Y
authors.lastname: Sakagami
mesh_terms: D000595:Amino Acid Sequence; D001412:Bacillus subtilis; D011756:Diphosphates / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry*; D005204:Farnesol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009387:Neoprene / Q000737:chemistry*; D010675:Pheromones / Q000378:metabolism*; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D011756:Diphosphates; D004224:Diterpenes; D010675:Pheromones; C511282:geranyl diphosphate; C016077:prenyl; C037088:farnesylacetic acid; D005204:Farnesol; D014364:Tryptophan; D009387:Neoprene