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. Author manuscript; available in PMC: 2021 Oct 28.
Published in final edited form as: J Am Chem Soc. 2020 Oct 14;142(43):18449–18459. doi: 10.1021/jacs.0c06877

Figure 6.

Figure 6.

Identification of PDMs representing fucosylated ascarosides. (a) EICs for PDMs bearing one or two deoxyhexose moieties that are further decorated with additional methyl groups in enriched probe-fed and control data sets. (b) MS/MS analysis of fucosylated ascr#3-LNK decorated with up to two methyl groups (36a–c, also Figures S15–S17). (c) EICs for m/z values corresponding to fucosas#10 (38) and derivatives with one or two additional methyl groups (fucosas#101 (39) and fucosas#102 (40), respectively) in acox-1.1, wildtype, and daf-22 exo-metabolomes. Fucosylated ascr#10 derivatives are observed in wild-type C. elegans, are more abundant in acox-1.1 mutants, and not detected in daf-22 mutant worms. Additional isomers of fucosylated ascr#10 derivatives represent fucosyl-ascarosides with shorter side chains and mono- and di-O-methylation of the fucose, as suggested by MS/MS analysis (Figures S18–S20). (d) EICs for fucosas#10 (38) in acox-1.1 exo-metabolome (black), a synthetic sample (green), and in a sample where synthetic fucosas#10 is added to acox-1.1 exo-metabolome (purple) confirm identification of fucosas#10. (e) Ascr#10 (34) and fucosas#10 (38) were quantified in the exo-metabolome of wildtype worms. Production of fucosas#10 is dependent on nutritional conditions, but not strongly dependent on life stage, unlike ascr#10.