Microbial biotransformation of ayrl sulfanylpentafluorides

Emma Kavanagh, Michael Winn, Cliona Nic Gabhann, Neil K. O’Connor, Petr Beier, Cormac D. Murphy*

School of Biomolecular and Biomedical Science, Centre for Synthesis and Chemical Biology, Ardmore House, University College Dublin, Dublin 4, Ireland

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Supplemental information

Fig S1. Total ion chromatogram of organic extract from Pseudomonas knackmussii without any addition of aryl-SF5.

Fig S2. TIC of control flask containing 3 in the absence of bacterium. The MS of derivatised 3 is shown below the chromatogram (retention time=6.1 min).

Fig S3. TIC of culture extract from P. knackmussii after incubation with 3. The MS of the product at 6.62 min shown below (indicated with an arrow)

Fig S4. TIC of control flask containing 4 in the absence of bacterium. The MS of derivatised 4 is shown below the chromatogram (5.9 min).

Fig S5. TIC of culture extract from P. knackmussii after incubation with 4. The MS of the product at 6.87 min shown below.

Fig S6. TIC of control flask containing 5 in the absence of bacterium. The MS of derivatised 5 is shown below the chromatogram (4 min).


Fig S7. TIC of culture extract from P. knackmussii after incubation with 5. The MS of the product at 4.39 min shown below.

Fig S8. TIC of control flask containing 6 in the absence of bacterium. The MS of derivatised 6 is shown below the chromatogram (7.15 min).

Fig S9. TIC of culture extract from P. knackmussii after incubation with 6. The MS of the products at 7.88 and 8.18 min shown below.

Fig S10. Incubation of Cunninghamella elegans with 1. Top chromatogram is a control flask without 1; middle is after incubation with 1; bottom is the MS of the product at 2.92 min.

Fig S11. GC-MS analysis of silylated extracts following incubation of S. griseus cell free extract with 3 in the presence (A) and absence (B) of acetyl CoA. The compound eluting at 9.51 min (indicated with arrow) has the mass spectrum of the N-acetylated product; the compound eluting just before was also present in a control experiment in which 3 and acetyl CoA were incubated in the absence of cell free extract.