1. Life through a cytochrome P450 lens David R. Nelson University of Tennessee, Memphis

2. FUNGI ANIMALS PLANTS PROTISTS ARCHAEA BACTERIA 2872 3387 91 2 18 239 1384

3. Plants Animals Fungi Bacteria Protists Archaea Increases by Taxon 1455 593 383 291 29 10

4. Medicago truncatula Carica papaya Selaginella mollendorffii Pinot noir

5. Daphnia pulex

6. Lauric acid Camphor terpineol Linalool CYP111A1CYP108A1CYP107A1 CYP107B1CYP101A1CYP102A1 CYP105A3 Pravastatin CYP165A3 Vancomycin CYP171A1CYP177A1 RDX Ethyl tert-butyl ether CYP249A1CYP167A1CYP153A6 C6-C11 Alkanes CYP129A2 CYP131A1 CYP131A2

10. 3305 P450s from seawater + 519 named P450s = 3824 seqs. Cluster with CD-HIT @ 90% 2211 clusters Select one representative seq. from each cluster Cluster with CD-HIT @ 60% 1143 clusters Make seq. align. with Muscle Filter out short sequences 566 sequence alignment Make NJ tree Select one representative seq. from each cluster

11. From Shibu Yooseph at JCVI S S S o E LB1 LB2 105/107 153 108

13. Clan Family moss rice papaya Arabidopsis Populus Vitis Chlamydomonas Selaginella CYP85 clanCYP72 clan First CYP88 90, 707 seqs Clan Family Chlamydomonas moss Selaginella rice papaya Arabidopsis Populus Vitis CYP71 clan core eudicot CYPs core angiosperm CYPs core land plant CYPs Phenylpropanoid pathway gibberellin pathway

14. 51 97 710 74 86 94 704 73 78 98 701 703 Land plant core New in Selaginella 96 75 76 92 71 706 84 79 81 89 93 85 87 722 729 728 723 724 72 709 734 735 715 714 727 New in angiosperms 77 88 90 707 711 New in eudicots 80 82 83 712 716 718 720 736 algae Sterols Carotenoids Oxylipins CutinsC4HC3H Gibberellin 1 Gibberellin 2, Brassinosteroids Abscissic acid Pollen formation Fatty acids fruit ripening lignin glucosinolates more brassinosteroids flavonoids pigments Alkaloids and more secondary metabolites

15. CYP75 Family expansion in grapevine papayaArabidopsis Populus Vitis Genes

16. CYP76 Family expansion in grapevine papaya Arabidopsis Populus Vitis Genes

17. CYP82 Family expansion in grapevine papaya Arabidopsis Populus Vitis Genes

18. Fungal cytochrome P450s

19. 60% of fungal P450 families have only 1 or 2 sequences. CYP51 CYP52 CYP61 CYP65 1384 named fungal CYPs 329 families

20. Zn(II) 2 Cys 6 fungal specific transcription factors Polyketide synthases (PKS) Nonribosomal peptide synthases (NRPS) Transporters of the MFS or ABC families (efflux pumps) Cytochrome P450s Flavin monooxygenases Methyl, acetyl or prenyl transferases dehydrogenases