ライフサイエンスコーパス: hydroxybenzoate

1 negative charge of the phenolic oxygen of p-hydroxybenzoate.

2 ) at a rate about 1% of that with 3-chloro-4-hydroxybenzoate.

3 for the unnatural substrates benzoate and 3-hydroxybenzoate.

4 involving the hydroxylation of benzoate to 4-hydroxybenzoate.

5 ffective catalyst for the hydroxylation of p-hydroxybenzoate.

6 l mutations completely blocked growth with 4-hydroxybenzoate.

7 enzoate, ethyl 4-ethoxybenzoate, and ethyl 4-hydroxybenzoate.

8 cid from undetectable levels to 0.6 microM 2-hydroxybenzoate.

9 quinone biosynthetic pathway, 3-hexaprenyl-4-hydroxybenzoate.

10 d for metabolism of protocatechuate and meta-hydroxybenzoate.

11 nd to citrate, and weakly to gentisate and 4-hydroxybenzoate.

12 orm a hydroperoxide, which then oxygenates p-hydroxybenzoate.

13 orm a hydroperoxide, which then oxygenates p-hydroxybenzoate.

14 orm a hydroperoxide, which then oxygenates p-hydroxybenzoate.

15 ate form in the presence of high levels of p-hydroxybenzoate.

16 e of the naturally incorporated monolignol p-hydroxybenzoates.

17 4-hydroxyphenyl)-4-pentylfuran-3-yl)-ethyl-4-hydroxybenzoate (1), 2-2-[(4-hydroxybenzoyl)-oxy]-ethyl-

18 late 2-hydroxybenzoate, 3-hydroxybenzoate, 4-hydroxybenzoate, 2,3-dihydroxybenzoate, 2,4-dihydroxyben

19 activator of pobA, the structural gene for 4-hydroxybenzoate 3-hydroxylase.

20 dehalogenase and thioesterase activities, 4-hydroxybenzoate 3-monooxygenase, and protocatechuate 3,4

21 The enzyme did not decarboxylate 2-hydroxybenzoate, 3-hydroxybenzoate, 4-hydroxybenzoate, 2

22 ion by 3-chlorobenzoate, 2-chlorobenzoate, 4-hydroxybenzoate, 3-hydroxybenzoate, and benzoate.

23 e that catalyzes the para-hydroxylation of 3-hydroxybenzoate (3HB) to form 2,5-dihydroxybenzoate (2,5

24 talyzes the hydrolysis of 4-HB-CoA to form 4-hydroxybenzoate (4-HB) and coenzyme A (CoA) in the final

25 ake the universal CoQ head group precursor 4-hydroxybenzoate (4-HB) from tyrosine is unknown.

26 synthesize the CoQ(10) headgroup precursor 4-hydroxybenzoate (4-HB)(7), offers an opportunity to phar

27 sses the ability of P. putida to transport 4-hydroxybenzoate (4-HBA) by preventing transcription of p

28 Chemotaxis to the aromatic acid 4-hydroxybenzoate (4-HBA) by Pseudomonas putida is mediate

29 tural genes required for the conversion of 4-hydroxybenzoate (4-HBA) to benzoyl-CoA by Rhodopseudomon

30 se from Pseudomonas putida that transports 4-hydroxybenzoate (4-HBA), were required for 4-HBA transpo

31 e did not decarboxylate 2-hydroxybenzoate, 3-hydroxybenzoate, 4-hydroxybenzoate, 2,3-dihydroxybenzoat

32 (a) of the bound substrate analog 4-fluoro-3-hydroxybenzoate (4F3HB) by 1.6 pH units, consistent with

33 show that the Fe-O bond of the monodentate 4-hydroxybenzoate (4HB) inhibitor complex is significantly

34 pecificity switch from the native effector 4-hydroxybenzoate (4HB).

35 nd that the single-component monooxygenase 3-hydroxybenzoate 6-hydroxylase (3HB6H) depresses the pK(a

36 3-Hydroxybenzoate 6-hydroxylase (3HB6H) from Rhodococcus j

37 3-Hydroxybenzoate 6-hydroxylase (3HB6H) from Rhodococcus j

38 diate involved in ubiquinone biosynthesis, 4-hydroxybenzoate, activates marRAB transcription in the a

39 emonstrated that 2,6-dihydroxybenzoate and 2-hydroxybenzoate altered kinase activity of CheA.

40 PobR responds to the inducer-metabolite p-hydroxybenzoate and activates transcription of pobA, the

41 transcriptional activator that responds to p-hydroxybenzoate and activates transcription of pobA.

42 e catalyzes the hydrolysis of 4-HBA-CoA to 4-hydroxybenzoate and CoA.

43 l genes that convert the related compounds 4-hydroxybenzoate and cyclohexanecarboxylate to benzoyl-Co

44 rom phenolic compounds including p-cresol, 4-hydroxybenzoate and numerous lignin monomers, to beta-ke

45 that catabolism of the phenolic compounds p-hydroxybenzoate and protocatechuate via the beta-ketoadi

46 e accumulation of two aromatic substrates, 4-hydroxybenzoate and protocatechuate, against a concentra

47 is known to metabolize this substrate via 4-hydroxybenzoate and protocatechuate, and evidence consis

48 bility to accumulate micromolar amounts of 4-hydroxybenzoate and protocatechuate.

49 lignin-related natural aromatic compounds, 4-hydroxybenzoate and vanillate, and the plastics-related

50 and PcaK have overlapping specificity for p-hydroxybenzoate and, most clearly, for protocatechuate:

51 , 1,2-phenylenebis(methylene) bis(3-fluoro-4-hydroxybenzoate), and 1,4-phenylenebis(methylene) bis(3-

52 oate, 2-chlorobenzoate, 4-hydroxybenzoate, 3-hydroxybenzoate, and benzoate.

53 the pK(a) of the phenolic oxygen of bound p-hydroxybenzoate, and eliminates the pH dependence of the

54 Details of the substrate, p-hydroxybenzoate, and substrate analog, p-aminobenzoate,

55 raben, BPF, PFOSAA, benzophenone-3, benzyl p-hydroxybenzoate, and triphenyl phosphate-by running a ma

56 etic analyses indicate 4-aminobenzoate and 4-hydroxybenzoate are preferred acyl substrates as PBS3 ex

57 Ethyl 4-hydroxybenzoate at 1 mM, like benzocaine, elicited littl

58 ith known benzoyl-CoA pathway inducers (para-hydroxybenzoate, benzoate, or cyclohexanoate), protocate

59 pendent chemotaxis to vanillate, vanillin, 4-hydroxybenzoate, benzoate, protocatechuate, quinate, shi

60 was reduced at a rate similar to that with p-hydroxybenzoate bound at high pH.

61 al conformation of the reduced enzyme with p-hydroxybenzoate bound.

62 t that was unable to grow anaerobically on 4-hydroxybenzoate but grew normally on benzoate.

63 ct quickly with halogen oxidants (i.e., para-hydroxybenzoate) but did not affect the degradation of a

64 oenzyme A during short-term uptake of [14C]4-hydroxybenzoate, but benzoyl coenzyme A was the major ra

65 ecause anaerobic growth of R. palustris on 4-hydroxybenzoate, but not on benzoate, was retarded unles

66 lso forms an open conformation for binding p-hydroxybenzoate, but only transiently.

67 ct was attributed to the degradation of para-hydroxybenzoate by hypohalous acids, which were produced

68 First, the rate of hydroxylation of p-hydroxybenzoate by the transiently formed flavin hydrope

69 rythraea strain 34H encodes a 3-octaprenyl-4-hydroxybenzoate carboxylase (CpsUbiX, UniProtKB code: Q4

70 3-fluoro-4-hydroxybenzoate (FHB), 3-chloro-4-hydroxybenzoate (CHB), and 3-iodo-4-hydroxybenzoate (IHB

71 g frames, divergently transcribed from the 4-hydroxybenzoate coenzyme A ligase gene, hbaA, were ident

72 this organism converts 4-chlorobenzoate to 4-hydroxybenzoate consists of three enzymes: 4-chlorobenzo

73 enzymatic reaction product, suggesting that hydroxybenzoates could be developed into useful drugs fo

74 te-, and metal-ion-independent, reversible 4-hydroxybenzoate decarboxylase (4-HOB-DC) from the obliga

75 chol branch, was consumed in preference to p-hydroxybenzoate, degraded via the protocatechuate branch

76 e (MHB), 4-hydroxybenzoate (PHB), 3-fluoro-4-hydroxybenzoate (FHB), 3-chloro-4-hydroxybenzoate (CHB),

77 hardly detectable, and the mutant required 4-hydroxybenzoate for growth underlining the importance of

78 The mutant PobR depended on p-hydroxybenzoate for its activity, but this dependence co

79 on yields vanillate from acetovanillone or 4-hydroxybenzoate from 4-hydroxyacetophenone.

80 Until recently, it has not been clear how p-hydroxybenzoate gains access to the buried active site.

81 cylated; poplar lignins, for example, have p-hydroxybenzoate groups on 1-15% of their syringyl subuni

82 ransgenic wood released fewer ester-linked p-hydroxybenzoate groups than control trees, and revealed

83 ve steps of isoprenyl tail polymerization, 4-hydroxybenzoate head-to-tail attachment, and head modifi

84 ydroxy-decanoic acid (10-HDAA), and methyl p-hydroxybenzoate (HOB) found at similar levels.

85 The flavin of p-hydroxybenzoate hydroxylase (PHBH) adopts two conformati

86 f several complexes involving FAD bound to p-hydroxybenzoate hydroxylase (PHBH) have revealed that th

87 p-Hydroxybenzoate hydroxylase (PHBH) hydroxylates activate

88 p-Hydroxybenzoate hydroxylase (PHBH) is a homodimeric enzy

89 p-Hydroxybenzoate hydroxylase (PHBH) is a homodimeric flav

90 p-Hydroxybenzoate hydroxylase (PHBH) is an FAD-dependent m

91 The FAD of p-hydroxybenzoate hydroxylase (PHBH) is known to exist in

92 cture can be assigned to the well-studied, p-hydroxybenzoate hydroxylase (PHBH) SCOP superfamily of f

93 ll architecture is most similar to that of p-hydroxybenzoate hydroxylase (PHBH), although there are s

94 have revealed two flavin conformations in p-hydroxybenzoate hydroxylase (PHBH), the in-position and

95 clarify the mechanism of hydroxylation by p-hydroxybenzoate hydroxylase (PHBH).

96 demonstrated two flavin conformations for p-hydroxybenzoate hydroxylase (PHBH).

97 sential steps in the reaction catalyzed by p-hydroxybenzoate hydroxylase (PHBH).

98 es that of the NADPH-dependent flavoenzyme p-hydroxybenzoate hydroxylase (PHBH).

99 step in the paradigm aromatic hydroxylase, p-hydroxybenzoate hydroxylase (PHBH): the oxidation of p-h

100 Biochemical comparison of PvdA to p-hydroxybenzoate hydroxylase (PHBH, from Pseudomonas fluo

101 verall fold of 3HB6H is similar to that of p-hydroxybenzoate hydroxylase and other flavoprotein aroma

102 atures with the canonical FAD-dependent para-hydroxybenzoate hydroxylase and represents the first str

103 The flavin cofactor in the enzyme para-hydroxybenzoate hydroxylase can assume two conformations

104 para-Hydroxybenzoate hydroxylase catalyzes a two-step reactio

105 A novel p-hydroxybenzoate hydroxylase enzyme detected by proteomic

106 Proline 293 of p-hydroxybenzoate hydroxylase from Pseudomonas aeruginosa

107 strate analog, p-aminobenzoate, binding to p-hydroxybenzoate hydroxylase have been elicited by Raman

108 Para-hydroxybenzoate hydroxylase is a flavoprotein monooxygen

109 para-Hydroxybenzoate hydroxylase is a flavoprotein monooxygen

110 p-Hydroxybenzoate hydroxylase is a flavoprotein monooxygen

111 p-Hydroxybenzoate hydroxylase is extensively studied as a

112 that the control of the flavin position in p-hydroxybenzoate hydroxylase represents a compromise betw

113 Apo-p-hydroxybenzoate hydroxylase was reconstituted using 2'-f

114 me flavin-dependent hydroxylases (notably, p-hydroxybenzoate hydroxylase), binding of the hydroxylati

115 Here, using the R220Q mutant form of para-hydroxybenzoate hydroxylase, we show that in the absence

116 of catalysis in RebC may resemble that of p-hydroxybenzoate hydroxylase, with substrate binding prom

117 of aromatic hydroxylases characterized by p-hydroxybenzoate hydroxylase.

118 chloro-4-hydroxybenzoate (CHB), and 3-iodo-4-hydroxybenzoate (IHB)] are reported at 2.0-2.2 A resolut

119 cis-muconate, inhibited the utilization of p-hydroxybenzoate in the presence of benzoate.

120 y by which 4-chlorobenzoate is degraded to 4-hydroxybenzoate in the soil-dwelling microbe Pseudomonas

121 network abstracts the phenolic proton from p-hydroxybenzoate in the transition state of oxygen transf

122 7 (2-fluoro-6-(m-hydroxybenzoyloxy) phenyl m-hydroxybenzoate) inhibits passive sugar transport in hum

123 We conclude that benzocaine and 4-hydroxybenzoate interact with the open and inactivated c

124 because (unlike wild-type) the binding of p-hydroxybenzoate is a rate-limiting process.

125 indicates that the deprotonation of bound p-hydroxybenzoate is also required for flavin movement, an

126 enolysis, it is generally assumed that the p-hydroxybenzoate is cleaved before the deacylated lignin

127 The anaerobic degradation of 4-hydroxybenzoate is initiated by the formation of 4-hydro

128 Salicylate (SA, 2-hydroxybenzoate) is a phytohormone best known for its ro

129 s compared with the metabolite-only model (4-hydroxybenzoate, isoleucine, carnitine, 2-hydroxyisovale

130 etate (MHP), 4-hydroxyphenylacetate (PHP), 3-hydroxybenzoate (MHB), 4-hydroxybenzoate (PHB), 3-fluoro

131 ML conjugates: ML-acetate, ML-benzoate, ML-p-hydroxybenzoate, ML-vanillate, ML-p-coumarate, and ML-fe

132 The p-hydroxybenzoate moiety itself also undergoes carboxylate

133 involved in the synthesis of the prenylated hydroxybenzoate moiety of the antibiotic, specifically c

134 ture of methylolanthanin exhibits a unique 4-hydroxybenzoate moiety which has not previously been des

135 novobiocin analogue, in which the 3-prenyl-4-hydroxybenzoate of novobiocin is replaced with a tetraen

136 This compound, differing from p-hydroxybenzoate only in that it contains an additional o

137 s of wild-type and mutant PHBH, with bound p-hydroxybenzoate or p-aminobenzoate, reveal a chain of pr

138 y genes blocking degradation of vanillate, p-hydroxybenzoate, or protocatechuate were selected.

139 oxybenzoate, 3,4,5-trihydroxybenzoate, 3-F-4-hydroxybenzoate, or vanillate.

140 e 4-hydroxybenzoyl-CoA, hydrolysis to form 4-hydroxybenzoate, oxidation to yield protocatechuate, and

141 zoate hydroxylase (PHBH): the oxidation of p-hydroxybenzoate (p-OHB).

142 The 4-hydroxybenzoate permease PcaK was shown to modulate the

143 nylacetate (PHP), 3-hydroxybenzoate (MHB), 4-hydroxybenzoate (PHB), 3-fluoro-4-hydroxybenzoate (FHB),

144 al changes caused by the binding of either p-hydroxybenzoate (pOHB) or 2,4-dihydroxybenzoate (2,4-diO

145 genase that catalyzes the hydroxylation of p-hydroxybenzoate (pOHB) to 3,4-dihydroxybenzoate in an NA

146 be in the in-position for hydroxylation of p-hydroxybenzoate (pOHB), whereas the out-position is esse

147 rotonation state of the aromatic substrate p-hydroxybenzoate (pOHB), which when ionized to the phenol

148 COQ2 (p-hydroxybenzoate polyprenyl transferase) encodes the enzy

149 le for decarboxylation of the 3-octaprenyl-4-hydroxybenzoate precursor.

150 used for the detection and quantitation of 4-hydroxybenzoate preservatives, methylparaben, ethylparab

151 structure of the H213S variant with bound 3-hydroxybenzoate provide hints about oxygen activation an

152 und to wt PHBH and wt PHBH plus substrate, p-hydroxybenzoate, provided examples of the "in" conformat

153 [1,3-phenylenebis(methylene) bis(3-fluoro-4-hydroxybenzoate) (RA-2), 1,2-phenylenebis(methylene) bis

154 nd iron-sulfur cluster-containing 3-chloro-4-hydroxybenzoate reductive dehalogenase from Desulfitobac

155 ich catalyzes the formation of two different hydroxybenzoate regioisomers, likely in a single active

156 nzoate, which are isomers of gentisate and 4-hydroxybenzoate respectively that are not metabolized by

157 g sets of enzymes that convert quinate and p-hydroxybenzoate, respectively, to protocatechuate.

158 lladium-assisted reactions on the cinnamyl p-hydroxybenzoates resulting in initial beta-ether cleavag

159 amycin synthetase is primed with a 3-amino-5-hydroxybenzoate starter unit by a loading module that co

160 ld not be bypassed by supplementation with 4-hydroxybenzoate, the immediate precursor of ubiquinone's

161 uinone biosynthesis and that the supply of 4-hydroxybenzoate, the side-chain shortened version of par

162 measure the pKa of the -OH group in bound p-hydroxybenzoate, the substrate was labeled with 18O in b

163 However, in the presence of the substrate p-hydroxybenzoate there is clear evidence from the Raman m

164 t are triggered by deprotonation of buried p-hydroxybenzoate through a H-bond network that leads to t

165 and oxygen-dependent para-hydroxylation of 3-hydroxybenzoate to 2,5-dihydroxybenzoate.

166 cted by demanding the inability to convert 4-hydroxybenzoate to a toxic metabolite.

167 genase that catalyzes the hydroxylation of p-hydroxybenzoate to form 3,4-dihydroxybenzoate.

168 rm a hydroperoxide, which then reacts with p-hydroxybenzoate to form an oxygenated product.

169 ormation is the mechanism for sequestering p-hydroxybenzoate to initiate catalysis.

170 ructural gene for the enzyme that converts p-hydroxybenzoate to protocatechuate.

171 enzyme by NADPH in response to binding of p-hydroxybenzoate to the enzyme and (2) oxidation of reduc

172 e phosphate (NADPH) in response to binding p-hydroxybenzoate to the enzyme and oxidation of reduced F

173 factor FAD by NADPH in response to binding p-hydroxybenzoate to the enzyme and reaction of reduced FA

174 ctor, FAD, by NADPH in response to binding p-hydroxybenzoate to the enzyme, and oxidation of reduced

175 Deprotonation of p-hydroxybenzoate to the phenolate and reprotonation of th

176 ive enzymes required for the conversion of 4-hydroxybenzoate to tricarboxylic acid cycle intermediate

177 For p-hydroxybenzoate, upon complexation, the -COO- symmetric

178 Benzoate inhibited 4-hydroxybenzoate uptake but was not a substrate for PcaK-

179 close to the pca-qui-pob gene cluster (for p-hydroxybenzoate utilization) and distant from the functi

180 These mutant enzymes bind p-hydroxybenzoate very fast, but with very low affinity, a

181 y two competitive pathways, one leading to 4-hydroxybenzoate via elimination of the enolpyruvyl side

182 The Vmax for uptake of 4-hydroxybenzoate was at least 25 nmol/min/mg of protein,

183 R. palustris was unable to grow when meta-hydroxybenzoate was provided as a sole source of organic

184 Methyl 2,3,4-tribromo-5-hydroxybenzoate was selected as starting compound becaus

185 dihydroxybenzoate (protocatechuate) and meta-hydroxybenzoate, was investigated in Rhodopseudomonas pa

186 Further, protocatechuate and meta-hydroxybenzoate were each removed from cultures containi

187 or cyclohexanoate), protocatechuate and meta-hydroxybenzoate were taken up from the culture medium.

188 ound strongly to 2,6-dihydroxybenzoate and 2-hydroxybenzoate, which are isomers of gentisate and 4-hy

189 n E. coli with conversion of chorismate to 4-hydroxybenzoate, which is then prenylated and decarboxyl

190 tic response by facilitating the uptake of 4-hydroxybenzoate, which leads to the accumulation of beta

191 nable to produce the key precursor 3-amino-5-hydroxybenzoate with either 7-demethylmitomycin A or 7-d

192 nder overloading conditions with eight alkyl hydroxybenzoates with nonideal conditions.

193 d 1,4-phenylenebis(methylene) bis(3-fluoro-4-hydroxybenzoate)] with inhibitory efficacy as determined

194 uted benzoates such as 4-aminobenzoate and 4-hydroxybenzoate, with moderate activity on benzoate and