Supplementary information

From the following article

Small-molecule pheromones that control dauer development in Caenorhabditis elegans

Rebecca A Butcher, Masaki Fujita, Frank C Schroeder & Jon Clardy

Nature Chemical Biology 3, 420 - 422 (2007) Published online: 10 June 2007

doi:10.1038/nchembio.2007.3

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Supplementary Fig. 1

NMR spectra of natural 1 in methanol-d4.

Supplementary Fig. 2

Key COSY interactions and HMBC interactions.

Supplementary Fig. 3

Establishing the stereochemistry of 1.

Supplementary Fig. 4

NMR spectra of synthetic 2 in methanol-d4.

Supplementary Fig. 5

Comparison of the activities of 1, 2, and 3 in the dauer formation assay in different mutant backgrounds at 20 °C.

Supplementary Fig. 6

Percent dauer formation in wild-type and daf-22 worms.

Supplementary Table 1

1H, 13C NMR and HMBC data for 1 in methanol-d4.

Supplementary Table 2

1H and 13C NMR data for 2 in acetone-d6 derived from dqf-COSY, HMQC, and HMBC spectra.

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