ライフサイエンスコーパス: methylphosphonate

1 e most bulky alkoxy moiety, S(P)-cycloheptyl methylphosphonate.

2 ve fluoro[5-methoxy-2-(pyrimidin-2-yl)phenyl]methylphosphonate.

3 re starved for phosphate, or when growing on methylphosphonate.

4 well as with Proteobacterial degradation of methylphosphonate.

5 t C2 of the substrate to the methyl group of methylphosphonate.

6 onverts 2-hydroxyethylphosphonate (2-HEP) to methylphosphonate.

7 cted phosphate in each strand with uncharged methylphosphonate.

8 on neutralizing the phosphate backbone with methylphosphonates.

9 0% less than duplexes neutralized by racemic methylphosphonates.

10 ctive substitution of backbone phosphates by methylphosphonates.

11 2-Aminoethyl methylphosphonate (2-AEMP), an analog of GABA, has been

12 e herein the total asymmetric synthesis of 3-methylphosphonate, 3-(monofluoromethyl)phosphonate and 3

13 ly catalyzes the hydrolysis of 4-nitrophenyl methylphosphonate (4NPMP).

14 olysed to pyrophosphate and alpha-D-ribose-1-methylphosphonate-5-phosphate (PRPn).

15 The cleavage of the C-P bond within ribose-1-methylphosphonate-5-phosphate to form methane and 5-phos

16 e reacts with MgATP to form alpha-D-ribose-1-methylphosphonate-5-triphosphate (RPnTP) and adenine.

17 and tested for their sensitivity to dimethyl methylphosphonate (a nerve agent simulant).

18 differentiation and quantitative analysis of methylphosphonate (a nerve gas byproduct), glyphosate (a

19 e increase in vapor sensitivity for dimethyl methylphosphonate (a Sarin simulant) detection using a s

20 3,4-dihydroxyphenethylamino) (quinolin-4-yl) methylphosphonate)-a newly discovered molecule that has

21 Methylphosphonate synthase (MPnS) produces methylphosphonate, a metabolic precursor to methane in t

22 charge-neutralized or substituted by neutral methylphosphonates across the major or minor groove have

23 d cyclic sulfamidate 22 with lithium dialkyl methylphosphonate, affording 13 and 23, respectively.

24 both ADP and its nonhydrolyzable alpha, beta-methylphosphonate analog were strong inhibitors of APAF-

25 Using the purine oligomer, d(AG)8, its methylphosphonate analog, d(AG)8, and the complementary

26 The 5-methylphosphonate analogue containing a 6-[3,5-bis(methy

27 results of the enzyme activity assays on the methylphosphonate and 2'-O-methyl-modified substrates.

28 imits of detection of 20 ppt(v) for dimethyl methylphosphonate and 40 ppt(v) for methyl salicylate.

29 erons of P. stutzeri abolishes all growth on methylphosphonate and aminoethylphosphonate.

30 Methylphosphonate and borate electrolytes support cataly

31 bound dimer ions were obtained with dimethyl methylphosphonate and butanone.

32 s were exposed to the CWA simulants dimethyl methylphosphonate and diethyl phosphoramidate as well as

33 At 3-15 mM Mg(2+), the all-methylphosphonate and DNA oligonucleotides trans-splice

34 These chimeric TFOs contain mixtures of methylphosphonate and phosphodiester internucleotide bon

35 n 2'-O-methylribonucleosides and alternating methylphosphonate and phosphodiester internucleotide lin

36 DNA duplexes with patches of alternating methylphosphonate and phosphodiester linkages are less b

37 The methylphosphonate and phosphodiester linkages of these o

38 complexes, the catalyzed hydrolysis of aryl methylphosphonates and aryl phosphates are much more sim

39 Electrolysis of Co(2+) in phosphate, methylphosphonate, and borate electrolytes effects the e

40 CWA) simulants trimethyl phosphate, dimethyl methylphosphonate, and diisopropyl methylphosphonate wer

41 applied to oligomers having phosphodiester, methylphosphonate, and phosphorothioate backbone linkage

42 Diphenyl methylphosphonate appears to be a fairly specific inhibi

43 However, the ability of OS-B' to utilize methylphosphonate as a sole phosphorus source occurred o

44 g methyl ethyl ketone, toluene, and dimethyl methylphosphonate as a test mixture.

45 the cells grew rapidly in fresh medium with methylphosphonate as the only source of phosphorus.

46 nd one mutant lacking the ability to grow on methylphosphonate as the sole P source was isolated.

47 s containing isomerically pure S(p) and R(p) methylphosphonates at single positions for the purpose o

48 d to triplex formation, the advantage of the methylphosphonate backbone on the purine strand is clear

49 may be offset by the reduced ability of the methylphosphonate backbone to assume an A-type conformat

50 -pyrimidinone residues or the base-sensitive methylphosphonate backbone.

51 ng pathways for putative photosynthetic- and methylphosphonate-based methane production also co-occur

52 Methylphosphonate-bearing oligonucleotides are character

53 trosopumilus maritimus encodes a pathway for methylphosphonate biosynthesis and that it produces cell

54 thway in metagenomic data sets suggests that methylphosphonate biosynthesis is relatively common in m

55 y either supplement N. maritimus' endogenous methylphosphonate biosynthesis pathway - which requires

56 Diphenyl methylphosphonate causes peroxisome clustering around oi

57 Stereochemistry at the methylphosphonate center for the heptanucleotide was eit

58 ) stereoisomer, although only one of the six methylphosphonate centers has the S(p) stereochemistry).

59 ribonucleotides and oligodeoxyribonucleoside methylphosphonates comprised exclusively of the fluoresc

60 ivation of a series of resolved enantiomeric methylphosphonate conjugates of acetylcholinesterase by

61 ssible only for alpha-amino (2-alkynylphenyl)methylphosphonates containing a benzene ring.

62 rmed between a single strand heptanucleotide methylphosphonate, d(Cp(Me)Cp(Me)Ap(Me)Ap(Me)Ap(Me)Cp(Me

63 We show methane is produced during methylphosphonate decomposition under phosphate-limiting

64 Chirally pure methylphosphonate deoxyribooligonucleotides were synthes

65 ntus, was determined as a complex with the N-methylphosphonate derivative of l-arginine (PDB code 3MT

66 was also determined as a complex with the N-methylphosphonate derivative of l-Pro (PDB code 3N2C ).

67 Use of isolated S(p) and R(p) methylphosphonate diastereomers demonstrates that interf

68 lants (dimethyl methylphosphonate, pinacolyl methylphosphonate, diethyl phosphoramidate, and 2-(butyl

69 mits of detection for acetonitrile, dimethyl methylphosphonate, diisopropyl methyl phosphonate in pos

70 ed from the stereochemically pure nucleoside methylphosphonate dimer building block, prepared as a ph

71 Two nerve agent simulants, diisopropyl methylphosphonate (DIMP) and di-methyl methylphosphonate

72 ion on the nerve agent simulants diisopropyl methylphosphonate (DIMP) and dimethyl methylphosphonate

73 agent (CWA) surrogate compound, diisopropyl methylphosphonate (DIMP), demonstrated that the HSA-SPME

74 three pairs of compounds, that is, dimethyl methylphosphonate (DMMP) and acetone, methyl tert-butyl

75 mical warfare agent (CWA) stimulant dimethyl methylphosphonate (DMMP) and several other standard comp

76 centration for the first time using dimethyl methylphosphonate (DMMP) as a test case.

77 id electrolyte with H(2) O by using dimethyl methylphosphonate (DMMP) as solvent or co-solvent to con

78 l impurity profiles from commercial dimethyl methylphosphonate (DMMP) samples to illustrate the type

79 to respond strongly to the analyte dimethyl methylphosphonate (DMMP) that simulates phosphonate nerv

80 ence enhancement at the presence of dimethyl methylphosphonate (DMMP) vapors.

81 propyl methylphosphonate (DIMP) and dimethyl methylphosphonate (DMMP) was studied while solutions of

82 (and their less reactive simulants, dimethyl methylphosphonate (DMMP)) as well as mustard (HD) in bot

83 xture of one G-type nerve simulant (dimethyl methylphosphonate (DMMP)) in four (water, kerosene, gaso

84 d 1300% for six analytes, including dimethyl methylphosphonate (DMMP), 3-octanone, and perfluorooctan

85 ropyl methylphosphonate (DIMP) and di-methyl methylphosphonate (DMMP), and three sorbent polymers wer

86 position of a nerve-agent simulant, dimethyl methylphosphonate (DMMP), on UiO-66, UiO-67, MOF-808, an

87 as been shown to react readily with dimethyl methylphosphonate (DMMP).

88 I) via a high dipole moment solvent dimethyl methylphosphonate (DMMP).

89 e, tetrabutylammonium chloride, and dimethyl methylphosphonate (DMMP).

90 A, phosphorothioate RNA, 2'-O-methyl RNA and methylphosphonate DNA.

91 Based on methylphosphonate-DNA mapping, pol eta interacts with th

92 We report the binding of methylphosphonate/DNA chimeras and neutral methylphospho

93 eavage for oligonucleotides substituted with methylphosphonates downstream from the cleavage site.

94 onate (IMPA), GB degradate; 61-91% for ethyl methylphosphonate (EMPA), VX degradate; and 60-98% for p

95 ational heterogeneity was confirmed with the methylphosphonate ester anion adduct of the active-site

96 The S(p) enantiomers of the methylphosphonate esters are far more reactive in formin

97 nthesis and that it produces cell-associated methylphosphonate esters.

98 on proton (third order) and proton acceptor, methylphosphonate (first order for 1.8 mM </= [MeP(i)] <

99 where phosphorus-starved microbes catabolize methylphosphonate for its phosphorus.

100 (1mp) where PS is trimethylpsoralen and p is methylphosphonate, forms a stable triplex with env-DNA w

101 cid (IMPA) and O-isopropyl O'-(2-amino)ethyl methylphosphonate (GB-MEA adduct).

102 Diisopropyl methylphosphonate, GB impurity, was not recovered from s

103 cid (PMPA) and O-pinacolyl O'-(2-amino)ethyl methylphosphonate (GD-MEA adduct).

104 Here, we report that introduction of a methylphosphonate group into the quinoxalinedione skelet

105 3'-terminal phosphodiester of the TFO with a methylphosphonate group significantly increased the resi

106 Substitution of neutral methylphosphonate groups for anionic DNA phosphate group

107 However, the introduction of chirally pure methylphosphonate groups shows that the effect of substi

108 ster linkages of T(pT)(8) were replaced with methylphosphonate groups.

109 s and lithiated methyl alpha-(trimethylsilyl)methylphosphonate has been developed.

110 Replacement of phosphates by neutral methylphosphonates has previously been shown to be a mod

111 At 15 mM Mg(2+), the nuclease-resistant all-methylphosphonate hexamer, d(AmTmGmAmCm)rU, with a seque

112 Both operons individually support growth on methylphosphonate; however, the phn operon supports grow

113 states for aryl phosphate monoester and aryl methylphosphonate hydrolysis reactions that are much mor

114 ermeable surfaces were 60-103% for isopropyl methylphosphonate (IMPA), GB degradate; 61-91% for ethyl

115 fuse reflection data are presented for ethyl methylphosphonate in a fine Utah dirt sample as a model

116 h the sodium salt of diethyl (phenylsulfonyl)methylphosphonate in DME at 140 degrees C for 4 h gives

117 ced P substrate hypophosphite, phosphite, or methylphosphonate, in addition to excess Pi, did not res

118 with a methyl group by the introduction of a methylphosphonate instead of the natural phosphate in fu

119 ly rapid hydrolysis of a covalent enzyme-DNA methylphosphonate intermediate.

120 phate neutralization by substituting neutral methylphosphonate internucleoside linkages at relevant p

121 ntaining microbes supports the proposal that methylphosphonate is a source of methane in the upper, a

122 In these organisms, methylphosphonate is converted to phosphate and methane.

123 en suggested to explain this phenomenon, yet methylphosphonate is not a known natural product, nor ha

124 es neutralized by incorporation of pure (RP)-methylphosphonate isomers are bent approximately 30% les

125 2AEP (Stappia stellulata AepX K(d) 23 4 nM; methylphosphonate K(d) 3.4 0.3 mM).

126 osphate groups with an uncharged (R)- or (S)-methylphosphonate linkage (MeP).

127 perator sequence and a single diastereomeric methylphosphonate linkage are each prepared from the ste

128 by showing that introduction of an Sp or Rp methylphosphonate linkage at the cleavage site transform

129 onucleotides prepared with these R(P) chiral methylphosphonate linkage synthons bind RNA with signifi

130 d by the asymmetric incorporation of racemic methylphosphonate linkages creating a neutral region on

131 o presence and possibly the chirality of the methylphosphonate linkages in the oligomer.

132 AAGGA), where MP corresponds to positions of methylphosphonate linkages in the pure R(p) stereoconfig

133 When two of the methylphosphonate linkages in the region complementary t

134 Surrounding the GTG sequence with nonionic methylphosphonate linkages inhibited or eliminated cross

135 substrates persisted unabated when multiple methylphosphonate linkages were inserted between the sit

136 basic tetrahydrofuran linkages, neutralizing methylphosphonate linkages, and conformationally locked

137 he AP-1 site with various numbers of neutral methylphosphonate linkages.

138 hen it is partially substituted with neutral methylphosphonate linkages.

139 scissile phosphate (P) by the charge neutral methylphosphonate (MeP) makes Arg-308 dispensable during

140 neutralization of the scissile phosphate via methylphosphonate (MeP) modification.

141 ubstitution of the scissile phosphate (P) by methylphosphonate (MeP) permits strand cleavage by a Cre

142 , we measured the kinetic effects of neutral methylphosphonate (MeP) stereoisomers at the +1 and +2 p

143 ive charge on the scissile phosphate through methylphosphonate (MeP) substitution does not stimulate

144 nucleotides, as well as phosphorothioate and methylphosphonate modifications within the tRNA acceptor

145 Our data with methylphosphonate-modified DNA suggests that thioredoxin

146 ds and experiments with different length and methylphosphonate-modified primer-templates demonstrate

147 were tested in enzyme activity assays on the methylphosphonate-modified substrates.

148 Methylphosphonate (MP) oligodeoxynucleotides (MPOs) are

149 een performed on a hybrid duplex formed by a methylphosphonate (MP) oligodeoxyribonucleotide (MPO) an

150 ng linkage between the microbial turnover of methylphosphonate (MPn) and the widespread methane overs

151 methanogenesis substrates found only (13) C-methylphosphonate (MPn) resulted in (13) CH4 generation.

152 These alternating oligonucleoside methylphosphonates, mr-AOMPs, contain 2'-O-methylribonuc

153 ospecific synthesis of chiral phosphines and methylphosphonate nucleotides are reported.

154 -resistant, 5'-psoralen-conjugated, chimeric methylphosphonate oligodeoxyribo- or oligo-2'-O-methylri

155 and synthesized a series of novel antisense methylphosphonate oligonucleotide (MPO) cleaving agents

156 eveals the first stereospecific synthesis of methylphosphonate oligonucleotide precursors.

157 f methylphosphonate/DNA chimeras and neutral methylphosphonate oligonucleotides to a ribozyme that is

158 ze the effects of a small molecule, diphenyl methylphosphonate, on oil mobilization in Arabidopsis th

159 ng enzyme activity assays on substrates with methylphosphonate or 2'-O-methyl substitutions.

160 Using exogenous nucleophiles and synthetic methylphosphonate or 5'-thiolate substrates, we decipher

161 phosphonate analogue containing a 6-[3,5-bis(methylphosphonate)]phenylazo moiety, 9, had IC50 values

162 nt antisense effects induced by the chimeric methylphosphonate-phosphodiester compounds were found to

163 In conclusion, the chimeric methylphosphonate-phosphodiester oligodeoxynucleotides p

164 ssion was specifically disrupted by chimeric methylphosphonate/phosphodiester antisense oligodeoxynuc

165 thesized oligonucleotides having alternating methylphosphonate/phosphodiester internucleotide linkage

166 The application of methylphosphonate:phosphodiester chimaeric oligonucleoti

167 e of four G/V-type nerve simulants (dimethyl methylphosphonate, pinacolyl methylphosphonate, diethyl

168 n for the four additional diprotic oxyanions methylphosphonate (pK(a)s: 2.40, 8.00), benzylphosphonat

169 were hydrolyzed to the less toxic pinacolyl methylphosphonate (PMP), which is a common degradation p

170 MPA), VX degradate; and 60-98% for pinacolyl methylphosphonate (PMPA), GD degradate.

171 Here we show that methylphosphonate reacts with MgATP to form alpha-D-ribo

172 as been compared with the standard lithiated methylphosphonate reagent.

173 modified oligonucleotide possessed a single methylphosphonate replacement on the phosphate backbone,

174 six proximal phosphate residues with neutral methylphosphonates resulted in DNA bent spontaneously to

175 Of these analogs, only (R)-2-aminopropyl methylphosphonate significantly diminished the response

176 cissile phosphate by an electrically neutral methylphosphonate significantly impairs the rate of bond

177 detection of a pesticide simulant, dimethyl methylphosphonate sorbed onto silica gel (DMMP/SG), usin

178 nionic phosphates) and explore the effect of methylphosphonate stereochemistry.

179 The hybridization of the methylphosphonate strand does not perturb the structure

180 d effect on the hybridization ability of the methylphosphonate strand.

181 The results show that the methylphosphonate strands in the heteroduplexes exhibit

182 Molecular dynamics simulations on partially methylphosphonate substituted helical chains of d(TATAGG

183 The degree of DNA bending induced by methylphosphonate substitution (approximately 3.5 degree

184 ctive neutralization of phosphate charges by methylphosphonate substitution demonstrates the differen

185 5-Methylphosphonate substitution, anticipated to increase

186 half-site DNA were chemically neutralized by methylphosphonate substitution.

187 A series of further methylphosphonate substitutions and mutations and trunca

188 differential flexibility of duplex DNA when methylphosphonate substitutions are made and find that t

189 the AATT sequence is normally narrow and the methylphosphonate substitutions have a smaller but measu

190 onformation averaged over all stereospecific methylphosphonate substitutions is nearly the same as th

191 then compared the damaging effects of these methylphosphonate substitutions on catalysis with their

192 rivative of c-di-GMP containing 2'-deoxy and methylphosphonate substitutions that is charge neutral a

193 xamine this, we introduced single and tandem methylphosphonate substitutions through the region of th

194 further using DNA substrates carrying unique methylphosphonate substitutions, together with mutations

195 The enzymatic hydrolysis of a series of aryl methylphosphonate substrates yields a Bronsted beta(lg)

196 droxyethylphosphonate dioxygenase (HEPD) and methylphosphonate synthase (MPnS) are nonheme iron oxyge

197 Methylphosphonate synthase (MPnS) produces methylphospho

198 droxyethylphosphonate dioxygenase (HEPD) and methylphosphonate synthase (MPnS).

199 Methylphosphonate synthase is a non-heme iron-dependent

200 , identifying the molecular requirements for methylphosphonate synthesis.

201 The ability of chimeric methylphosphonate TFOs to bind to DNA, combined with the

202 -pentyl-4-biphenylcarbonitrile, and dimethyl methylphosphonate to metal cation models representing th

203 Cells sequentially limited by phosphate and methylphosphonate transformed >75% of their lipids to ph

204 were used to examine the effects of diphenyl methylphosphonate treatment on seedlings.

205 f three chemical warfare simulants, dimethyl methylphosphonate, triethyl phosphate, and dipropylenegl

206 acceleration in the rate of hydrolysis of a methylphosphonate versus phosphodiester suggests that re

207 The corresponding 5-methylphosphonate was equipotent at P2X1 receptors.

208 e of the two resulting diastereomers, the SP methylphosphonate, was compatible with efficient GTPase

209 dimethyl methylphosphonate, and diisopropyl methylphosphonate were captured by passing air through a

210 We found that a phosphorothioate and a methylphosphonate were excised with low efficiency.

211 a diethanolamine amide group and an aryl di(methylphosphonate) were both less potent than 10 as anta

212 , methyl ethyl ketone, toluene, and dimethyl methylphosphonate, were released from the packed column

213 I reagent ion leading to protonated dimethyl methylphosphonate, while the monomer is mainly responsib

214 thoxyphenyl)(fluoro)(pyrimidin-2-ylsulfonyl)]methylphosphonate with Bu(3)SnH resulted in an intramole

215 d high nuclease stability of the P-C bond of methylphosphonates with the high membrane permeability,