5932
C. M. Boehner et al. / Tetrahedron Letters 51 (2010) 5930–5932
petri dish
O
O
F
F
F
F
agar with
lawn of bacteria
N
H
activation of
quorum sensing
F
OH
F
F
O
F
n
O
n
O
O
O
O
BHL 25 n=2
HHL 26 n=4
Cl
O
n
gel slide
22 n=2
23 n=4
H2N
O
24
TFP gel spots -
'wall-less test-tubes'
phenotypic assay
active ester - 'catch'
-homoserine lactone) and HHL (hexanoyl-L-homoserine lactone) in TFP acrylamide gel spots. Gel spots were loaded with butyryl
amide - 'release'
Scheme 3. Synthesis of BHL (butanoyl-
L
chloride (22) or hexanyl chloride (23) before reaction with aminobutyrolactone (24) to produce BHL (25) and HHL (26), which were validated by LCMS. BHL and HHL could be
detected using quorum sensing phenotypic assays using Serratia sp. ATCC39006 (BHL) or Chromabacterium violaceum (HHL). For example, C. violaceum produces a purple
violaceum halo under HHL mediated quorum sensing.
(b) Salvino, J. M.; Kumar, N. V.; Orton, E.; Airey, J.; Kiesow, T.; Crawford, K.;
Mathew, R.; Krolikowski, P.; Drew, M.; Engers, D.; Krolikowski, D.; Herpin, T.;
Gardyan, M.; McGeehan, G.; Labaudiniere, R. J. Comb. Chem. 2000, 2, 691–697.
catch-and-release chemistry. Bioactive quorum-sensing molecules
were successfully synthesised in preparation for phenotypic assay
screening.
3. Ziauddin, J.; Sabatini, D. M. Nature 2001, 411, 107–110.
4. Bailey, S. N.; Sabatini, D. M.; Stockwell, B. R. Proc. Natl. Acad. Sci. U.S.A. 2004,
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We are grateful for financial support from EPSRC, BBSRC, Glaxo-
SmithKline, the Cambridge Trust and the Augustus Newman
Foundation.
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Supplementary data
Supplementary data associated with this article can be found, in
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