| Title: | The geranyl-modified tryptophan residue is crucial for ComXRO-E-2 pheromone biological activity |
| Author(s): | Tsuji F; Kobayashi K; Okada M; Yamaguchi H; Ojika M; Sakagami Y; |
| Address: | "Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan" |
| DOI: | 10.1016/j.bmcl.2011.04.123 |
| ISSN/ISBN: | 1464-3405 (Electronic) 0960-894X (Linking) |
| 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" |
| Keywords: | Amino Acid Sequence *Bacillus subtilis Diphosphates/*chemistry Diterpenes/*chemistry Farnesol/*analogs & derivatives/chemistry/pharmacology Molecular Sequence Data Molecular Structure Neoprene/*chemistry Pheromones/*metabolism Tryptophan/*chemistry; |
| Notes: | "MedlineTsuji, Fumitada Kobayashi, Ko Okada, Masahiro Yamaguchi, Hisao Ojika, Makoto Sakagami, Youji eng Research Support, Non-U.S. Gov't England 2011/06/04 Bioorg Med Chem Lett. 2011 Jul 1; 21(13):4041-4. doi: 10.1016/j.bmcl.2011.04.123. Epub 2011 May 12" |
