Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 21, Issue 13, Pages 4041-4044Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2011.04.123
Keywords
Bacillus subtilis; ComX pheromone; Posttranslational modification; Quorum sensing; Structure-activity relationships
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Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan [21 2118, 18101009]
- Grants-in-Aid for Scientific Research [18101009, 09J01228] Funding Source: KAKEN
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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 PheTrp/(Ger)-NH2 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. (C) 2011 Elsevier Ltd. All rights reserved.
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