Life through a cytochrome P 450 lens David

Life through a cytochrome P 450 lens David R. Nelson University of Tennessee, Memphis

PR OT 239 ISTS S T N 7 A PL 338 A FUNGI 1384 E HA C AR 18 S L A IM 2 N A 287 BA CT 91 ERI 2 A

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

Selaginella mollendorffii Carica papaya Medicago truncatula Pinot noir

Daphnia pulex

terpineol Linalool Lauric acid Camphor CYP 102 A 1 CYP 101 A 1 CYP 107 B 1 CYP 108 A 1 CYP 111 A 1 Pravastatin RDX Vancomycin CYP 105 A 3 CYP 165 A 3 Ethyl tert-butyl ether CYP 249 A 1 CYP 171 A 1 CYP 177 A 1 C 6 -C 11 Alkanes CYP 167 A 1 CYP 153 A 6 CYP 129 A 2 CYP 131 A 1 CYP 131 A 2

3305 P 450 s from seawater + 519 named P 450 s = 3824 seqs. Cluster with CD-HIT @ 90% 2211 clusters Select one representative seq. from each cluster Cluster with CD-HIT @ 60% 1143 clusters Select one representative seq. from each cluster Make seq. align. with Muscle Filter out short sequences 566 sequence alignment Make NJ tree

LB 1 From Shibu Yooseph at JCVI LB 2 105/107 Eo S 153 108 S S

Vitis Populus Arabidopsis papaya rice Selaginella moss Chlamydomonas core eudicot CYPs core angiosperm CYPs core land plant CYPs gibberellin pathway Phenylpropanoid pathway Family Clan Vitis Populus CYP 71 clan Arabidopsis papaya rice Selaginella moss Chlamydomonas Family Clan First CYP 88 90, 707 seqs CYP 85 clan CYP 72 clan

Land plant core 51 97 710 74 86 94 704 73 78 98 701 703 algae Oxylipins Cutins Sterols Carotenoids C 4 H C 3 H Pollen formation Gibberellin 1 New in Selaginella 77 88 90 707 711 Gibberellin 2, Brassinosteroids Abscissic acid New in angiosperms 96 75 76 92 71 706 84 79 81 89 93 85 87 722 729 728 723 724 72 709 734 735 714 727 Fatty acids fruit ripening lignin glucosinolates more brassinosteroids flavonoids pigments New in eudicots 80 82 83 712 716 718 720 736 Alkaloids and more secondary metabolites

CYP 75 Family expansion in grapevine Genes Vitis papaya Arabidopsis Populus

CYP 76 Family expansion in grapevine Vitis Populus Genes Arabidopsis papaya

CYP 82 Family expansion in grapevine Vitis Genes Populus papaya Arabidopsis

Fungal cytochrome P 450 s

CYP 65 CYP 52 1384 named fungal CYPs CYP 51 CYP 61 329 families 60% of fungal P 450 families have only 1 or 2 sequences.

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 P 450 s Flavin monooxygenases Methyl, acetyl or prenyl transferases dehydrogenases