ライフサイエンスコーパス: hydroperoxy

1 singlet oxygen addition was observed to give hydroperoxy-1,2-dioxenes 19 and 20 in an ene-diene trans

2 yrrolidinyloxyl (DMPO-OH) and 2,2-dimethyl-5-hydroperoxy-1-pyrrodinyloxyl (DMPO-OOH) whose hyperfine

3 sed, but none of them oxidized 18:2n-6 to 9R-hydroperoxy-10(E),12(Z)-octadecadienoic acid (9R-HPODE).

4 ation and 9-hydroxy-10,12-octadecadienoate/9-hydroperoxy-10,12-octadecadieno ic acid production by mo

5 of F(2)-8alpha isoprostanes (isoprostane), 9-hydroperoxy-10,12-octadecadienoic acid (9-HODE), 13-hydr

6 at it produced a mixture of 30% 9S-HPODE (9S-hydroperoxy-10E, 12Z-octadecadienoic acid) and 70% 13S-H

7 ration, whereas it is nearly racemic from 9S-hydroperoxy-10E,12Z-octadecadienoic acid (9S-HPODE).

8 9-Hydroperoxy-12-oxo-10E-dodecenoic acid is >90% S when de

9 that retains the original carboxyl group (9-hydroperoxy-12-oxo-10E-dodecenoic acid).

10 to a 9,12-dihydroperoxide leads to chiral 9S-hydroperoxy-12-oxo-10E-dodecenoic acid.

11 decenoic acid, which oxygenates to racemic 9-hydroperoxy-12-oxo-10E-dodecenoic acid; by contrast, (ii

12 products, which we identified as 9R- and 9S-hydroperoxy-12S,13S-trans-epoxyoctadec-10E-enoic acids.

13 By comparison, the corresponding 15-hydroperoxy, 15-hydroxy, 8,15-dihydroxy, and 5,15-dihydr

14 etabolites of docosahexaenoic acid (DHA), 17-hydroperoxy-, 17-hydroxy-, 10,17-dihydroxy-, and 7,17-di

15 exadiene (5), while the other, which forms 1-hydroperoxy-2,4-cyclohexadiene (18), passes through the

16 (DeltaH(double dagger) = 8.8 kcal/mol) to 1-hydroperoxy-2,5-cyclohexadiene (5), while the other, whi

17 ogen peroxide, conversion of the resulting 4-hydroperoxy-2-alkanols to 3-alkoxy-1,2-dioxolanes, and L

18 Incubation of CatA with 2-hydroperoxy-2-methylcyclohexanone led to formation of 5,

19 Recent evidence points to 4-hydroperoxy-2E-nonenal (4-HPNE) as the immediate precurs

20 l product of 3Z-nonenal (NON) oxidation is 4-hydroperoxy-2E-nonenal (4-HPNE).

21 eral peroxyquinols, including 2-tert-butyl-4-hydroperoxy-4-methylcyclohexa-2,5-dien-1-one (BMPOOH) an

22 n the case of glycyl-tyrosine, a stable 3-(1-hydroperoxy-4-oxocyclohexa-2,5-dien-1-yl)-L-alanine was

23 bited AA- or CI-mediated production of 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid [1

24 drogenase (PGDH)-mediated oxidation of 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid wa

25 15(S)-Hydroperoxy-5,8,11-cis-13-trans-eicosatetraenoic acid, a

26 M; turnover, 3.69 +/- 0.09 min(-1)), and 15S-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (K(m), 1

27 ver, 4.51 +/- 0.13 min(-1)), followed by 12S-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (K(m), 2

28 15(S)-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid is the m

29 he major lipid peroxidation product was 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid, w

30 In the present study, 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid (5-HpETE), r

31 ide derivatives were formed ((2S,3aR,7aR)-3a-hydroperoxy-6-oxo-2,3,3a,6,7,7a-hexahydro-1H-indole-2-ca

32 OX) requiring the formation of 5-HPETE [5(S)-hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid] a

33 7 microM; turnover, 3.7 +/- 0.1 min(-1)), 5S-hydroperoxy-6E,8Z,11Z,14Z-eicosatetraenoic acid (K(m), 2

34 tion of the 5- lipoxygenase metabolite, 5(S)-hydroperoxy-(6E,8Z,11Z, 14Z)-eicosatetraenoic acid.

35 nal theory which agreed with the structure 5-hydroperoxy-8-oxo-7,8-dihydroguanosine.

36 LeAOS was active against both 13S-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid (13-H

37 Inactivation requires 13-hydroperoxy-9(Z),11(E)-octadecadienoic acid (13-HPOD), w

38 5(Z)-octadecatrienoic acid (13-HPOT) and 13S-hydroperoxy-9(Z),11(E)-octadecadienoic acid, whereas LeH

39 hidonic acid (AA)), and the products (13-(S)-hydroperoxy-9,11-(Z,E)-octadecadienoic acid (HPOD) and 1

40 competitive inhibitor versus the product, 13-hydroperoxy-9,11-(Z,E)-octadecadienoic acid, with a K(i)

41 of linoleic acid and by decomposition of 13-hydroperoxy-9,11-octadecadienoate (13-HPODE), especially

42 octadecadienoic acid) and 70% 13S-HPODE (13S-hydroperoxy-9Z, 11E-octadecadienoic acid) at pH 7.

43 be enhanced by spiking the reaction with 13S-hydroperoxy-9Z, 11E-octadecadienoic acid.

44 fatty acid hydroperoxides revealed that 13S-hydroperoxy-9Z,11E-octadecadienoic acid (13-HpODE) was t

45 nalysis revealed that 4-HPNE formed from 13S-hydroperoxy-9Z,11E-octadecadienoic acid (13S-HPODE) reta

46 The lipid hydroperoxide 13(S)-hydroperoxy-9Z,11E-octadecadienoic acid (HpODE) is found

47 s monoepoxides, cis,trans-2,4-alkadienals, 4-hydroperoxy- and 4-hydroxy-2-alkenals, and several vitam

48 yphenyl)phosphine, namely, the corresponding hydroperoxy arylphosphine and a hydroxy phosphorane.

49 beta-hydroxy-5-oxo-5,6-secocholestan-6-al, 5-hydroperoxy-B-homo-6-oxa-cholestan-3beta,7a-diol, and 5b

50 he cyanobacterium Anabaena PCC 7120 forms 9R-hydroperoxy-C18.3omega3 in a lipoxygenase domain, then a

51 trans-10, cis-12-octadecadienoic acid and 13-hydroperoxy-cis-9, trans-11-octadecadienoic acid.

52 -1 cells, whereas anti-B4-bR combined with 4-hydroperoxy-cyclophosphamide caused additive killing of

53 aldehyde-to-carboxylic acid product or as a hydroperoxy derivative 7'' that evolved into an electrop

54 15-Hydroperoxy derivatives of AA and 2-AG were found to be

55 ied the inactivating lipids as the 9- and 13-hydroperoxy derivatives of cholesteryl linoleate, choles

56 For 9-hydroxy and 9-hydroperoxy derivatives of oxidized PS, the sn-2 ester b

57 in the reaction of iron with the putative 4a-hydroperoxy-DMPH4 leads to 4a-hydroxy-DMPH4 and a high v

58 Its natural reaction is to convert 8R-hydroperoxy-eicosatetraenoic acid (8R-HPETE) to an allen

59 role in cleaving the lipoxygenase product 8R-hydroperoxy-eicosatetraenoic acid into the short-chain a

60 individual molecular species of hydroxy- and hydroperoxy-eicosatetraenoic acids (H(P)ETEs), F(2)-isop

61 n added exogenously to cells, 5-, 12- and 15-hydroperoxy-eicosatetraenoic acids also over-oxidized pe

62 peroxide lyase activity specific for the 10S-hydroperoxy enantiomer.

63 rough base-catalyzed disproportionation of a hydroperoxy endoperoxide available by singlet oxygenatio

64 product of this isomerization is a dihydroxy hydroperoxy epoxide (C5H10O5), which is expected to have

65 e involvement of specific intermediates (C4a-hydroperoxy-FAD and C4a-hydroxy-FAD) in the reaction, de

66 abled the detection of low concentrations of hydroperoxy fatty acid derived from lipoxygenase activit

67 enases are a class of dioxygenases that form hydroperoxy fatty acids with distinct positional and ste

68 ) and their products, especially 9S- and 13S-hydroperoxy fatty acids, could play a role in the Asperg

69 he Thr(252) accepts a hydrogen bond from the hydroperoxy (Fe(III)-OOH) intermediate that promotes the

70 n of NOHA to citrulline and HNO/NO(-) is the hydroperoxy-ferric form (5).

71 agent that hydroxylates CH, rather than the hydroperoxy-ferric heme.

72 In this process, the hydroperoxy-ferric intermediate decays with a large solv

73 During annealing of the hydroperoxy-ferric P450scc intermediates at 185 K, they

74 x trapped at 77 K produces predominantly the hydroperoxy-ferriheme P450scc intermediate, along with a

75 phytin b peroxylactone or (15(1)S, 17R, 18R)-hydroperoxy-ficuschlorin D (16), together with twelve kn

76 Two oxygenated flavin intermediates C(4a)-hydroperoxy flavin and C(4a)-hydroxy flavin were found,

77 or flavin oxidation in which C4a-peroxy and -hydroperoxy flavin intermediates accumulate to detectabl

78 275P and alphaF261D were able to form the 4a-hydroperoxy-FMN intermediate II but at lower yields.

79 nding site may interact with the substrate's hydroperoxy group and play an important role in catalysi

80 re consumed per mol HPETE, and loss of HPETE hydroperoxy group occurs with retention of the conjugate

81 rophage was consistent with reduction of a 5-hydroperoxy group to an intermediate alkoxy radical that

82 ly oxygenated intermediates with one or more hydroperoxy groups are prevalent in the autooxidation of

83 fter formation of an intermediate flavin C4a-hydroperoxy hemiacetal.

84 nds (conjugated dienes in chains having also hydroperoxy/hydroxy groups, epoxides and aldehydes); the

85 Hydroperoxy, hydroxyl and carbonyl-substituted CPA deriv

86 r molecules to provide stabilization for the hydroperoxy intermediate and to serve as a conduit to th

87 mplex and promotes conversion of the ferrous hydroperoxy intermediate obtained by reduction of the fe

88 further reduction of the oxy complex to the hydroperoxy intermediate resulting in heterolytic cleava

89 uential pathway where H(2)O(2) first forms a hydroperoxy intermediate Ti-OOH (15.4 kcal/mol activatio

90 d, it favors the stabilization of the ferric-hydroperoxy intermediate, Fe(3+)-OOH(-), which serves as

91 p(136) (Asp(140) in hHO) that stabilizes the hydroperoxy intermediate.

92 These results also show that the reactive hydroperoxy intermediates are generally characterized by

93 ants model for P450, which postulates that a hydroperoxy-iron species (or a protonated analogue of th

94 The enzyme efficiently metabolized 9-hydroperoxy linoleic acid and 9-hydroperoxy linolenic ac

95 Incubation of recombinant CYP74D with 9-hydroperoxy linoleic acid and 9-hydroperoxy linolenic ac

96 using 9-/13-hydroperoxy linolenic and 9-/13-hydroperoxy linoleic acids as substrates.

97 LOX3, A451G eLOX3, and soybean LOX-1 with 13-hydroperoxy-linoleic acid forms oxygenated end products,

98 acid while linoleic acid is converted to 9S-hydroperoxy-linoleic acid in lower efficiency.

99 etabolized 9-hydroperoxy linoleic acid and 9-hydroperoxy linolenic acid but was poorly active against

100 ydroperoxides, whereas OsHPL3 metabolizes 13-hydroperoxy linolenic acid exclusively.

101 lyzes the first step in the conversion of 13-hydroperoxy linolenic acid to jasmonic acid and related

102 YP74D with 9-hydroperoxy linoleic acid and 9-hydroperoxy linolenic acid yielded divinyl ether fatty a

103 rmined by in vitro enzyme assays using 9-/13-hydroperoxy linolenic and 9-/13-hydroperoxy linoleic aci

104 12R-LOX forms 9R-hydroperoxy-linoleoyl-omega-hydroxyceramide, further con

105 re antagonizing enzymes in the metabolism of hydroperoxy lipids.

106 n-6 and 18:3n-3 to 13R-, 11(S or R)-, and 9S-hydroperoxy metabolites ( approximately 80-85, 15-20, an

107 th Ile changed the stereochemistry of the 13-hydroperoxy metabolites of 18:2n-6 and 18:3n-3 (from app

108 C-13 toward C-9 with formation of 9S- and 9R-hydroperoxy metabolites of 18:2n-6 and 18:3n-3.

109 g from the interaction of ascorbic acid with hydroperoxy octadecadienoic acid in vitro, were identifi

110 c LPO products from the lipid hydroperoxide, hydroperoxy octadecadienoic acid.

111 (H(P)ETEs), F(2)-isoprostanes, hydroxy- and hydroperoxy-octadecadienoic acids (H(P)ODEs), and their

112 acid), along with hydroperoxides (9- and 13-hydroperoxy-octadecadienoylglycerol species).

113 ter accumulation of its product, the free 13-hydroperoxy octadecatrienoic acid (13-HPOT), 2 days afte

114 The 17alpha-hydroperoxy (OOH) derivatives of the steroids were used

115 Our density functional theory study of hydroperoxy (OOH) intermediates on various model titanos

116 free radical-induced fragmentation of either hydroperoxy- or hydroxyoctecadienoate esters of 2-lyso-P

117 formed from [18O]15S-HPETE showed that both hydroperoxy oxygens are retained in the product.

118 bstrate demonstrated 97.6% retention of both hydroperoxy oxygens in the major product with progressiv

119 d and C12 aldehyde with the retention of the hydroperoxy oxygens, consistent with synthesis of a shor

120 Inadequate reduction of hydroperoxy-PE due to insufficiency or dysfunction of a

121 anges their substrate competence to generate hydroperoxy-PE.

122 centrations, the second-generation dihydroxy hydroperoxy peroxy radical (C5H11O6.) must undergo an in

123 c response in SHE cells, and 13-HODE and its hydroperoxy precursor are potent and highly specific enh

124 e arachidonic acid: the human enzyme, a 15-S-hydroperoxy product; and the murine enzyme, an 8-S-produ

125 The composition of the conjugated hydroperoxy products formed after oxidation differed mar

126 The di(hydroperoxy)propane adducts are soluble in organic solve

127 Additionally, the corresponding di(hydroperoxy)propane adducts R3PO(HOO)2CMe2 (R=Cy, Ph) we

128 lts provide insight into a new source of the hydroperoxy radical (HO2 ) in the troposphere.

129 alculations to predict the energetics of the hydroperoxy radical (HO2) in the presence of an (H2O)20

130 gether with the closely coupled species, the hydroperoxy radical, HO(2), is intimately involved in th

131 semiquinone-like organic species, and (iii) hydroperoxy radicals.

132 in placing a water molecule to stabilize the hydroperoxy species and as a template for the condensati

133 Fe(III)Fe(III) (P) intermediate to a 1,1-mu hydroperoxy species, which abstracts an H atom from the

134 o oxidize NON to 4-HPNE with an excess of 4S-hydroperoxy-stereoisomer.

135 4-HPNE was demonstrated to be 83% of the 4S-hydroperoxy-stereoisomer.

136 ong LOX in being autocatalytic, in which the hydroperoxy substrate is isomerized to the epoxyalcohol

137 ptor separations around the coelenterazine-2-hydroperoxy substrate, initiated by small spatial adjust

138 olecular pathways for decomposition of alpha-hydroperoxy sulfides are suggested to rationalize the su

139 Evidence is presented that suggests that the hydroperoxy sulfonium ylide exists in both diradical and

140 the sulfone is formed via rearrangement of a hydroperoxy sulfonium ylide intermediate.

141 are analyzed in terms of partitioning of the hydroperoxy sulfonium ylide intermediate.

142 number of persulfoxides, thiadioxiranes, and hydroperoxy sulfonium ylides were located and their stru

143 xidase activity with cumene hydroperoxide, 9-hydroperoxy-trans-10, cis-12-octadecadienoic acid and 13