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26 results for “hydroperoxides”
Fig. 2 in Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Identification of allene oxide synthase (CYP74L2) and hydroperoxide lyase (CYP74L1)
Fig. 2. The structural formulae of products of recombinant enzyme incubations with different substrates. 1, 12-oxo-13-hydroxy-9,15-octadecadienoic acid; 2, 12-oxo-13-hydroxy-9-octadecenoic acid; 3, 9- hydroxy-10-oxo-12,15-octadecadienoic acid; 4, 9-hydroxy-10-oxo-12-octadecenoic acid; 5, 11-hydroxy- 12,13-epoxy-9-octadecenoic acid; 5a, 11-hydroxy- 12,13-epoxy-9,15-octadecadienoic acid; 6, 9,10- epoxy-11-hydroxy-12-octadecenoic acid; 6a, 9,10- epoxy-11-hydroxy-12,15-octadecadienoic acid; 7, 9- hydroxynonanoic acid; 8, (9Z)-12-hydroxy-9-dodecenoic acid; 9, (10E)-12-hydroxy-10-dodecenoic acid; R, -(CH2)7COOH.
Fig. 1 in Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Identification of allene oxide synthase (CYP74L2) and hydroperoxide lyase (CYP74L1)
Fig. 1. The multiple alignment of the CYP74L1, CYP74L2, and CYP74L3 sequences of S. moellendorffii. Conservative structures are marked as follows: the I-helix groove region (SRS-4) is numbered 1–6, two positions after the I-helix groove region are marked by ▾ symbol, the F/L toggle, the ERR-triad, the PPV domain, and the cysteinyl ligand are marked by ◆, ●, □, and ◊ symbols, respectively.
Fig. 4 in Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Identification of allene oxide synthase (CYP74L2) and hydroperoxide lyase (CYP74L1)
Fig. 4. The TIC GC–MS chromatograms of products (Me/TMS) of incubations of the recombinant CYP74L2 with 13-HPOT (A), 13-HPOD (B), 9-HPOT (C), and 9-HPOD (D). Conditions of incubation, extraction, derivatisation and analysis are described in Materials and Methods. 1a, 1b (threo and erythro isomers of 12,13-dihydroxy-9,15-octadecadienoic acid (the products of the α-ketol 1 reduction with NaBH4)); 2a, 2b (threo and erythro isomers of 12,13- dihydroxy-9-octadecenoic acid (the products of the α-ketol 2 reduction with NaBH4)); 3a, 3b (threo and erythro isomers of 9,10-dihydroxy-12,15-octadecadienoic acid (the products of the α-ketol 3 reduction with NaBH4)); 4a, 4b (threo and erythro isomers of 9,10- dihydroxy-12-octadecenoic acid (the products of the α-ketol 4 reduction with NaBH4)); 7, 9-hydroxynonanoic acid; 5, 11-hydroxy-12,13-epoxy-9-octadecenoic acid; 5a, 11-hydroxy-12,13-epoxy-9,15-octadecadienoic acid; 6, 9,10-epoxy-11-hydroxy-12-octadecenoic acid; 6a, 9,10-epoxy-11-hydroxy-12,15-octadecadienoic acid; 7, 9-hydroxynonanoic acid; 8, (9Z)-12-hydroxy-9-dodecenoic acid; 9, (10E)-12-hydroxy-10- dodecenoic acid. The structural formulae of products are present at Fig. 2. 9-HOT, (9S,10E,12Z,15Z)-9-hydroxy-10,12,15-octadecatrienoic acid.
Fig. 6 in Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Identification of allene oxide synthase (CYP74L2) and hydroperoxide lyase (CYP74L1)
Fig. 6. The multiple alignment of the CYP74L1, CYP74L2, and CYP74L3 sequences of S. moellendorffii with other CYP74s described earlier. Conservative structures are marked as follows: the I-helix groove region (SRS-4) is numbered 1–6, two positions after the I-helix groove region are marked by ◆ symbol, the F/L toggle is marked by ▾ symbol.
Fig. 7 in The CYP74B and CYP74D divinyl ether synthases possess a side hydroperoxide lyase and epoxyalcohol synthase activities that are enhanced by the site-directed mutagenesis
Fig. 7. The unrooted phylogenetic tree of the CYP74 family. Classified CYP74 subfamilies are marked with their letter designations (A, B, C, etc.). Subfamilies consisting of more than one member are outlined with unclosed curves (semi-ellipses). The following CYP74s were used for analysis: As, A. sativum; AsDES (CYP74H1), CAI30435.1; At, Arabidopsis thaliana; AtAOS (CYP74A1), NP199079.1; AtHPL (CYP74B2), C74B2ARATH; Ca, C. annuum; CaHPL (CYP74B1), NP001311810.1; CaDES (CYP74D4), NP001311513.1; Cas, Camellia sinensis; CasHPL (CYP74B24), BAU24783.1; Cs, Cucumis sativus; CsHPL/EAS/AOS (CYP74C31), XP004137005.1; CsHPL/EAS (CYP74C1_Cs), NP001274399.1; Cm, Cucumis melo; CmHPL/EAS (CYP74C2), NP001284390.1; Dc, Daucus carota; DcAOS (CYP74B33), XP_017248700.1; Gm, G. max; GmAOS (CYP74A1), NP001236432.1; GmHPL/EAS (CYP74C13_Gm), KRH29541.1; Hv, Hordeum vulgare, HvAOS2 (CYP74A3), CAB86384.1; Le, L. esculentum; LeAOS1 (CYP74A1), CAB88032.1; LeAOS2 (CYP74A2), AAF67141.1; LeAOS3 (CYP74C3), NP001265949.1; LeHPL (CYP74B3), AAF67142.1; LeDES (CYP74D1), NP001234527.1; Lu, L. usitatissimum; LuAOS (CYP74A1), sp|P48417.1; LuDES (CYP74B16), ADP03054.2; Mp, M. polymorpha, MpAOS1, BAS32647.1; MpAOS2, BAS32648.1; Mt, Medicago truncatula; MtHPL/EAS (CYP74C13_Mt), XP003606860.1; MtHPL3 (CYP74B4), AAY30368.1; Nt, N. tabacum; NtDES (CYP74D3), NP001312606.1; Os, Oryza sativa; OsAOS1 (CYP74A4), XP015631686.1; OsHPL2 (CYP74E1), EAY85033.1; Pa, Parthenium argentatum; PaAOS (CYP74A1), sp| Q40778.2; Pd, Prunus dulcis; PdHPL (CYP74C5), CAE18065.1; Pg, Psidium guajava; PgHPL (CYP74B5), AAK15070.1; Pi, Petunia inflata; PiCYP74C9, ABC75838.1; Pp, P. patens; PpAOS1 (CYP74A1), XP024380613.1; PpAOS2 (CYP74A8), XP024372097.1; PpHPL (CYP74G1), CAC86920.2; Ra, R. acris; RaDES (CYP74Q1), AJU57209.1; Rj, R. japonicus; RjEAS (CYP74A88), QCR70269.1; Sm, S. moellendorffii; SmDES1 (CYP74M1), XP002979266.1; SmDES2 (CYP74M3), XP002964012.2; SmEAS (CYP74M2), EFJ26024.1; St, S. tuberosum; StAOS2 (CYP74A6), ABD15175.1; StAOS3 (CYP74C10), CAI30876.1; StHPL/EAS (CYP74C4), XP006365486.1; StDES (CYP74D2), NP001305517.1; Zm, Zea mays; ZmAOS1 (CYP74A19), AAR33048.1; ZmHPL (CYP74F2), NP_001105255.2. The multiple alignments of selected CYP74 amino acid sequences and phylogenetic tree building were made with MEGA7 software. Multiple alignment was performed using the ClustalW method, phylogenetic tree was build using the maximum likelihood method based on the Poisson correction model (Zuckerkandl and Author- Anonymous, 1965); the bootstrap consensus tree was inferred from 1000 replicates (Felsenstein, 1985). The analysis involved 45 amino acid sequences.
Fig. 6 in The CYP74B and CYP74D divinyl ether synthases possess a side hydroperoxide lyase and epoxyalcohol synthase activities that are enhanced by the site-directed mutagenesis
Fig. 6. The mechanisms of fatty acid hydroperoxide conversions by target DESs. R = HOOC(CH2)7–, R' = n-butyl.
Fig. 4 in The CYP74B and CYP74D divinyl ether synthases possess a side hydroperoxide lyase and epoxyalcohol synthase activities that are enhanced by the site-directed mutagenesis
Fig. 4. GC-MS analyses of products (Me/TMS) of recombinant WT LuDES incubations with 9(S)-HPOD (A), 9(S)-HPOT (B), 13(S)-HPOD (C), and 13(S)- HPOT (D). 2, 9,10-epoxy-11-hydroxy-12-octadecenoic acid (Me/TMS); 3, 9- hydroxynonanoic acid (Me/TMS); 5, 9,10-epoxy-11-hydroxy-12,15-octadecadienoic acid (Me/TMS); 6, 11-hydroxy-12,13-epoxy-9-octadecenoic acid (Me/ TMS); 7, (ω5Z)-etherolenic acid (Me); 8, (9Z)-12-hydroxy-9-dodecenoic acid (Me/TMS); 9, (10E)-12-hydroxy-10-dodecenoic acid (Me/TMS); 10, 11-hydroxy-12,13-epoxy-9,15-octadecadienoic acid (Me/TMS); 12, 9-hydroxy- 12,13-epoxy-10-octadecenoic acid (Me/TMS); 13, 9,10-epoxy-13-hydroxy- 11,15-octadecadienoic acid (Me/TMS); 14, 9,10-epoxy-13-hydroxy-11-octadecenoic acid (Me/TMS). The structural formulae of products are presented in Fig. 2. 9-HOD/T and 13-HOD/T are decrypted in Fig. 3.
Fig. 3 in The CYP74B and CYP74D divinyl ether synthases possess a side hydroperoxide lyase and epoxyalcohol synthase activities that are enhanced by the site-directed mutagenesis
Fig. 3. GC-MS analyses of products (Me/TMS) of recombinant NtDES incubations with 9(S)-HPOD (A), 9(S)-HPOT (B), 13(S)-HPOD (C), and 13(S)- HPOT (D). 1, colneleic acid (Me); 2, 9,10-epoxy-11-hydroxy-12-octadecenoic acid (Me/TMS); 3, 9-hydroxynonanoic acid (Me/TMS); 4, colnelenic acid (Me); 4a, (3′E)-colnelenic acid (Me); 6, 11-hydroxy-12,13-epoxy-9-octadecenoic acid (Me/TMS). The structural formulae of products are presented in Fig. 2. 9-HOD, (9S,10E,12Z)-9-hydroxy-10,12-octadecadienoic acid; 9-HOT, (9S,10E,12Z,15Z)-9-hydroxy-10,12,15-octadecatrienoic acid; 13-HOD, (9Z,11E, 13S)-13-hydroxy-9,11-octadecadienoic acid; 13-HOT, (9Z,11E,13S,15Z)-13- hydroxy-9,11,15-octadecatrienoic acid.
Fig. 2 in The CYP74B and CYP74D divinyl ether synthases possess a side hydroperoxide lyase and epoxyalcohol synthase activities that are enhanced by the site-directed mutagenesis
Fig. 2. Structural formulae of reaction products of target WT enzymes and their mutant forms. 1, colneleic acid; 2, 9,10-epoxy-11-hydroxy-12-octadecenoic acid; 3, 9-hydroxynonanoic acid; 4, colnelenic acid; 4a, (3′E)-colnelenic acid; 5, 9,10-epoxy-11-hydroxy-12,15-octadecadienoic acid; 6, 11-hydroxy-12,13-epoxy-9-octadecenoic acid; 7, (ω5Z)-etherolenic acid; 8, (9Z)-12-hydroxy-9-dodecenoic acid; 9, (10E)-12-hydroxy-10-dodecenoic acid; 10, 11-hydroxy-12,13-epoxy-9,15-octadecadienoic acid; 11, (ω5Z)-etheroleic acid; 12, 9-hydroxy-12,13-epoxy-10-octadecenoic acid; 13, 9,10-epoxy-13-hydroxy-11,15-octadecadienoic acid; 14, 9,10-epoxy- 13-hydroxy-11-octadecenoic acid. (3′E)-Colnelenic acid is a product of thermal isomerization of the ordinary (8E,1′E,3′Z,6′Z)-colnelenic acid occurring during the GC analyses.
Fig. 1 in The CYP74B and CYP74D divinyl ether synthases possess a side hydroperoxide lyase and epoxyalcohol synthase activities that are enhanced by the site-directed mutagenesis
Fig. 1. Multiple alignments of I-helix sequences of following CYP74s: As, Allium sativum; AsDES, CAI30435; Ca, Capsicum annuum; CaDES, ABH03632; CaHPL, AAK27266; Cs, Citrus sinensis; CsAOS, NP_001275835; Gm, Glycine max; GmAOS, NP_001236445; Le, Solanum lycopersicum; LeHPL, CAB43022; LeDES, AAG42261; Lu, Linum usitatissimum; LuDES, ADP03054; Na, Nicotiana attenuata; NaAOS, CAC82911; Nt, Nicotiana tabacum; NtDES, AAL40900; NtHPL, AAZ39884; Ra, Ranunculus acris; RaDES, CYP74Q1, AJU57209; Sm, Selaginella moellendorffii; SmDES1, CYP74M1, EFJ19674; SmDES2, CYP74M3, EFJ34345; St, Solanum tuberosum; StDES, CAC28152. Hydroperoxide-binding domain is circled. Sites with substitutions are marked with arrows.
Fig. 5 in The CYP74B and CYP74D divinyl ether synthases possess a side hydroperoxide lyase and epoxyalcohol synthase activities that are enhanced by the site-directed mutagenesis
Fig. 5. GC-MS analyses of products (Me/TMS) of LuDES F291V mutant form incubations with 9(S)-HPOD (A), 9(S)-HPOT (B), 13(S)-HPOD (C), and 13(S)- HPOT (D). 2, 9,10-epoxy-11-hydroxy-12-octadecenoic acid (Me/TMS); 3, 9- hydroxynonanoic acid (Me/TMS); 5, 9,10-epoxy-11-hydroxy-12,15-octadecadienoic acid (Me/TMS); 6, 11-hydroxy-12,13-epoxy-9-octadecenoic acid (Me/ TMS); 8, (9Z)-12-hydroxy-9-dodecenoic acid (Me/TMS); 9, (10E)-12-hydroxy- 10-dodecenoic acid (Me/TMS); 10, 11-hydroxy-12,13-epoxy-9,15-octadecadienoic acid (Me/TMS). The structural formulae of products are presented in Fig. 2. 9-HOD/T and 13-HOD/T are decrypted in Fig. 3.
Fig. 7 in Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Identification of allene oxide synthase (CYP74L2) and hydroperoxide lyase (CYP74L1)
Fig. 7. The scheme of catalytic mechanisms of the CYP74L enzymes.
The effect of tert-butyl hydroperoxide on hepatic multi-transcript patterns of the sentinel fish Lithognathus mormyrus
GEO Series GSE19216. Lithognathus mormyrus. 5 samples. Type: Expression profiling by array.
Transcriptomic analysis of Wt Mtb H37Rv and WhiB4 Complemented strains on treatment with 0.25 mM Cumene hydroperoxide (CHP) for 2 h at 37°C.
GEO Series GSE114045. Mycobacterium tuberculosis H37Rv. 6 samples. Type: Expression profiling by array.
Deletion of the fungus specific protein phosphatase Z1 exaggerates the consequences of oxidative stress elicited by tert-butyl-hydroperoxide in Candida albicans
GEO Series GSE134060. Candida albicans. 16 samples. Type: Expression profiling by array; Expression profiling by high throughput sequencing.
Cumene hydroperoxide stimulon and OhrR regulon in Chromobacterium violaceum
GEO Series GSE90551. Chromobacterium violaceum ATCC 12472; Chromobacterium violaceum. 6 samples. Type: Expression profiling by array.
Deletion of the fungus specific protein phosphatase Z1 exaggerates the consequences of oxidative stress elicited by tert-butyl-hydroperoxide in Candida albicans (Microarray expression)
GEO Series GSE133335. Candida albicans. 4 samples. Type: Expression profiling by array.
Deletion of the fungus specific protein phosphatase Z1 exaggerates the consequences of oxidative stress elicited by tert-butyl-hydroperoxide in Candida albicans (RNAseq data set)
GEO Series GSE133611. Candida albicans. 12 samples. Type: Expression profiling by high throughput sequencing.
Gene expression changes of Saccharomyces cerevisiae to linoleic acid hydroperoxide
GEO Series GSE47820. Saccharomyces cerevisiae; Schizosaccharomyces pombe. 6 samples. Type: Expression profiling by array.
Fig. 8 in Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Identification of allene oxide synthase (CYP74L2) and hydroperoxide lyase (CYP74L1)
Fig. 8. The unrooted phylogenetic tree of the CYP74 clan. Classified CYP74 subfamilies are marked with their letter designation (A, B, C etc.). Subfamilies consisting of more than one member are outlined with unclosed curves (semi-ellipses). Plant CYP74s: As, Allium sativum; AsDES, CYP74H1, GI:83414021; At, Arabidopsis thaliana; AtAOS, CYP74A1, GI:15239032; AtHPL, CYP74B2, GI:3822403; Ca, Capsicum annuum; CaHPL, CYP74B1, GI:1272340; Cm, Cucumis melo; CmHPL/EAS, CYP74C2, GI:14134199; Cs, C. sativus; CsHPL/EAS, CYP74C1, GI:101211324; CsHPL/EAS/AOS, CYP74C31 GI:101211574; Dc, Daucus carota; DcAOS, CYP74B33, GI:10821971; Gm, Glycine max; GmHPL/EAS (CYP74C13_Gm), KRH29541.1; Hv, Hordeum vulgare; HvAOS2, CYP74A3, GI:7452981; HvHPL, CYP74F3, GI: 22265998; Kf, K. flaccidum (green alga); KfAOS, SI:LC032459; Le, Solanum lycopersicum; LeAOS1, CYP74A1, GI:7581989; LeAOS2, CYP74A2, GI:7677376; LeAOS3, CYP74C3, GI:25991603; LeHPL, CYP74B3, GI:7677378; LeDES (CYP74D1), NP001234527.1; Lu, Linum usitatissimum; LuAOS, CYP74A1, GI:1352186; LuDES, CYP74B16, GI:379048766; Mp, M. polymorpha; MpAOS1, SI:LC032457.1, MpAOS2, SI:LC032458.1; Mt, Medicago truncatula; MtHPL3, CYP74B5, GI:63081244; MtHPL1/EAS, CYP74C13, GI:33504430; Nt, Nicotiana tabacum; NtDES, CYP74D3; GI: 107799697; Os, Oryza sativa; OsAOS, CYP74A4, GI:115455571; OsHPL1, CYP74E2, GI:115445057; OsHPL2, CYP74E1, GI:125538638; Pa, Parthenium argentatum; PaAOS, CYP74A1, GI:218511958; Pd, Prunus dulcis; PdHPL, CYP74C5, GI:33300600; Pg, Psidium guajava; PgHPL, CYP74B5, GI:13183137; Pi, Petunia inflata; PiCYP74C9, GI:85720841; Pp, P. patens; PpAOS1, CYP74A1, GI:22217985; PpAOS2, CYP74A8, GI:168014176; PpHPL, CYP74G1, GI:76057841; Ra, Ranunculus acris; RaDES, CYP74Q1, GI:768564485; Rj, Ranunculus japonicus; RjEAS, CYP74A88, SI:MK061531; Sm, S. moellendorffii; SmDES1, CYP74M1, GI:9660714; SmEAS, CYP74M2, GI:9637471 SmDES2, CYP74M3, GI:9654395; SmAOS2, CYP74K3, EFJ20163.1; CYP74L1, XP002969700.1; CYP74L2, XP002972651.1; CYP74L3, EFJ25870.1; St, Solanum tuberosum; StAOS2, CYP74A6, GI:86769479; StAOS3, CYP74C10, GI:56605358; StHPL/EAS, CYP74C4, GI:102588560; StDES, CYP74D2, GI:12667099; Zm, Zea mays; ZmAOS, CYP74A19, GI:223947589; ZmHPL, CYP74F2, GI:162462890. CYP74 clan members: Es, E. siliculosus (brown alga); EsEAS, CYP5164B1, GI:1109557544; Mn, M. nodulans (proteobacteria); MnHPL, SI:WP_015932840.1; Msp, Methylobacterium sp. 4–46; MspCYP74, SI:WP_012335549.1. Ap, A. palmata (Metazoa); ApAOS, GI:187948710; Bf, B. floridae (Metazoa); BfEAS, CYP440A1, GI:189312561; Nv, N. vectensis (Metazoa); NvEAS, CYP443D1, GI:5516222; NvHPL/EAS CYP443C1 (GenBank QJI54761.1).
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