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 e detect and characterize the intermediate 2-hydroperoxy-2-hydroxypropanoate in real time and at high

19 The hyperpolarized reaction intermediate 2-hydroperoxy-2-hydroxypropanoate is detected in a single

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

21 rophilic lipid oxidation products, such as 4-hydroperoxy-2-nonenal and 2,4-decadienal, were found to

22 Adding exogenous 4-hydroperoxy-2-nonenal to an emulsion led to overall high

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

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

25 and tested by the pyrolysis of synthesized 3-hydroperoxy-3-phenylpropionate.

26 and Met427 on STARD3 are oxidized by 6alpha-hydroperoxy-3beta-hydroxycholest-4-ene (cholesterol-6alp

27 cholesterol-6alpha-hydroperoxide) and 7alpha-hydroperoxy-3beta-hydroxycholest-5-ene (cholesterol-7alp

28 simulations with biosynthetic precursor 17S-hydroperoxy-4,7,10,13,19-cis-15-trans-docosahexaenoic ac

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

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

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

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

33 15(S)-Hydroperoxy-5,8,11-cis-13-trans-eicosatetraenoic acid, a

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

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

36 15(S)-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid is the m

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

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

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

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

41 7 microM; turnover, 3.7 +/- 0.1 min(-1)), 5S-hydroperoxy-6E,8Z,11Z,14Z-eicosatetraenoic acid (K(m), 2

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

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

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

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

46 5(Z)-octadecatrienoic acid (13-HPOT) and 13S-hydroperoxy-9(Z),11(E)-octadecadienoic acid, whereas LeH

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

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

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

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

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

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

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

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

55 m-dihydroperoxides or peroxysilyl alcohols/B-hydroperoxy alcohols to generate the corresponding endop

56 The conversion of amines to hydroperoxy amides may have important implications for n

57 dation efficiently leads to the formation of hydroperoxy amides, a new type of atmospheric nitrogen-c

58 Hydroxy, hydroperoxy, and keto products of 2-arachidonoyl-lysoPI

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

60 s characterized by excessive accumulation of hydroperoxy-arachidonoyl (C20:4)- or adrenoyl (C22:4)- p

61 osis, decreases the level of pro-ferroptotic hydroperoxy-arachidonoyl-phosphatidylethanolamine, reduc

62 helial cells (HAECs) generate proferroptotic hydroperoxy-arachidonoyl-phosphatidylethanolamines (HpET

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

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

65 was obtained by theoretical calculation of 3-hydroperoxy butanal and tested by the pyrolysis of synth

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

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

68 -1 cells, whereas anti-B4-bR combined with 4-hydroperoxy-cyclophosphamide caused additive killing of

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

70 15-Hydroperoxy derivatives of AA and 2-AG were found to be

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

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

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

74 tabolites such as glycogenin, L-carnitine, 5-hydroperoxy eicosatetraenoic acid, and leukotriene B4, w

75 MS, we screened autoxidation reactions of 11-hydroperoxy-eicosatetraenoic acid (11-HpETE) and thereby

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

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

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

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

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

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

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

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

84 ductive dead-end complex, which prevents C4a-hydroperoxy-FAD formation when HadA is premixed with aro

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

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

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

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

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

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

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

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

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

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

95 (+) binding is required for formation of C4a-hydroperoxy flavin adenine dinucleotide (FAD) (FAD(C4aOO

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

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

98 275P and alphaF261D were able to form the 4a-hydroperoxy-FMN intermediate II but at lower yields.

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

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

101 cilitate the transfer of a proton from the 2-hydroperoxy group of the chromophore coelenterazine to b

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

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

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

105 O), formaldehyde (CH(2)O), hydroxyl (OH) and hydroperoxy (HO(2)) radicals are simultaneously detected

106 and lipids, leads to the accumulation of 15-hydroperoxy (Hp)-arachidonoyl-phosphatidylethanolamine (

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

108 Hydroperoxy, hydroxyl and carbonyl-substituted CPA deriv

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

127 12R-LOX forms 9R-hydroperoxy-linoleoyl-omega-hydroxyceramide, further con

128 re antagonizing enzymes in the metabolism of hydroperoxy lipids.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

144 anges their substrate competence to generate hydroperoxy-PE.

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

146 traditionally considered an iron dependent, hydroperoxy-phospholipid executed process, which induces

147 nzymatically driven accumulation of specific hydroperoxy-phospholipid species and iron-dependent redu

148 autophagy by 15LO1-PEBP1 complexes and their hydroperoxy-phospholipids reveals a pathobiologic pathwa

149 initial robust but selective accumulation of hydroperoxy polyunsaturated fatty acid-containing phosph

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

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

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

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

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

155 ns by 10-40% to 9.7 x 10(5) molec cm(-3) and hydroperoxy radical (HO(2)) concentrations by 50-70% to

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

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

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

159 on of indoor OH, the transformation of OH to hydroperoxy radicals (HO(2)), and resulting spatial dist

160 necting the chemistries of hydroxyl (OH) and hydroperoxy radicals, oxidized nitrogen species and orga

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

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

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

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

165 4-HPNE was demonstrated to be 83% of the 4S-hydroperoxy-stereoisomer.

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

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

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

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

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

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

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

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