ライフサイエンスコーパス: diazirine

1 e, 3-(trifluoromethyl)-3-(m-[125I]iodophenyl)diazirine.

2 scaled up to provide multigram quantities of diazirine.

3 targets with an efficiency comparable to the diazirine.

4 uorous phase synthesis with a perfluorinated diazirine.

5 thane (DCE) by photolysis of the appropriate diazirines.

6 le-carbon insertion has been developed using diazirines.

7 f readily available unactivated olefins with diazirines.

8 on of biomolecular labeling experiments with diazirines.

9 with highly reactive and non-chemoselective diazirines.

10 In this work, we report using diazirine (1) as an electrophilic nitrogen source in a r

11 3-(Trifluoromethyl)-3-(m-[(125)I]iodophenyl)diazirine ([(125)I]TID) and [(3)H]tetracaine, an aromati

12 3-(trifluoromethyl)-3-(m-[(125)I]iodophenyl)diazirine ([(125)I]TID) and the phosphatidylcholine anal

13 3-Trifluoromethyl-3-(m-[(125)I]iodophenyl)diazirine ([(125)I]TID) has been shown to be a potent no

14 be 3-trifluoromethyl-3-(m-[(125)I]iodophenyl)diazirine ([(125)I]TID) to compare the state-dependent p

15 el 3-trifluoromethyl-3-(m-[(125)I]iodophenyl)diazirine ([(125)I]TID) was used to identify the amino a

16 3-(trifluoromethyl)-3-(m-[(125)I]iodophenyl)diazirine ([(125)I]TID) were performed.

17 e 3-(trifluoromethyl)-3-(m- [125I]iodophenyl)diazirine ([125I]-TID).

18 c probe 3-(trifluoromethyl)-3-(m-iodophenyl) diazirine ([125I]TID) and exposed to agonist for either

19 und 3-trifluoromethyl-3-(m-[125I]iodophenyl) diazirine ([125I]TID) has revealed important structural

20 th 3-(trifluoromethyl)-3-(m-[125I]iodophenyl)diazirine ([125I]TID) in the presence of phospholipid ve

21 with 3-trifluoromethyl-3-(m-[125I]iodophenyl)diazirine ([125I]TID) to determine functionality.

22 ic reagent 3-trifluoro-3-(m-[125I]iodophenyl)diazirine ([125I]TID) which partitions into membranes an

23 th 3-(trifluoromethyl)-3-(m-[125I]iodophenyl)diazirine ([125I]TID), a lipophilic probe, specific for

24 be 3-(trifluoromethyl)-3-(m-[125I]iodophenyl)diazirine ([125I]TID).

25 corresponding cyclic alpha,alpha"-dicarbonyl diazirine 2 (phi(350) = 0.024).

26 Diazirine 2 and the lithium salt of the corresponding co

27 i(254) = 0.31), while at longer wavelengths, diazirine 2 becomes an important byproduct (Phi(350) = 0

28 reaction, while at 355 nm, the formation of diazirine 2 becomes the predominant process (Phi(350) =

29 UV photolysis of diazirine 2 is accompanied by two competing processes: l

30 The UV irradiation of diazirine 2 leads to the loss of nitrogen and the Wolff

31 Mild heating of diazirine 2 produces quantitative yields of diazo Meldru

32 Benzocyclobutadienyl diazirine (2) was synthesized and reacted with hydroxide

33 although resulting in a common intermediate diazirine 3, which undergoes subsequent photoconversion

34 ing with [(3)H]21-[4-(3-(trifluoromethyl)-3H-diazirine-3-yl)benzoxy]allopregnanolone ([(3)H]21-pTFDBz

35 The photoactive diazirine 4, a potent SIRT2 inhibitor, was subjected to

36 compound however, a halogenated three-carbon diazirine 4, is a potent anesthetic, is apparently nonto

37 m the reaction of 3-chloro-3-(p-nitrophenoxy)diazirine (5) with tetrabutylammonium fluoride (TBAF) un

38 rated photochemically from the corresponding diazirines (6).

39 (Av) nitrogenase with two diazene analogues: diazirine, a photolabile diazene containing the azo (-N=

40 obotic synthesis of a peptide reacted with a diazirine-a process requiring 12 synthetic steps.

41 was photolabeled with three photo-activable diazirine alcohol analogs, 3-azioctanol, 7-azioctanol, a

42 Valence isomerization of 3H-diazirines also afforded diazo compounds.

43 we present the use of a photolabile curcumin-diazirine analogue, CRANAD-147, to induce changes in pro

44 minimalist linkers containing both an alkyl diazirine and a cyclopropene.

45 to impart structural diversity and introduce diazirine and alkyne functionalities for target capture

46 By positioning diazirine and alkyne groups in metabolically distinct re

47 in kinases, as well as trifluoromethylphenyl diazirine and alkyne moieties that allow covalent modifi

48 Compared with diazirine and benzophenone, two commonly used photoaffin

49 with extrusion of N2, leading to photostable diazirine and thiocarbodiimide derivatives.

50 ally competitive with the cyclization to 1 H-diazirines and hence rearrange to carbodiimides.

51 ular rearrangements to carbodiimides via 1 H-diazirines and imidoylnitrenes under both thermal and ph

52 ifunctional photo-cross-linkers that feature diazirines and N-hydroxy-succinimidyl carbamate groups,

53 The previously unknown difluoromethyl diazirines and the previously neglected trifluoromethyl-

54 reagent succinimidyl 4,4'-azipentanoate (NHS-diazirine), and the polyoxometalate cluster {P(8)W(48)}.

55 alities include aryl azides, diazocarbonyls, diazirines, and benzophenones.

56 Diazirines are an attractive class of potential molecula

57 These results indicate that alkyl diazirines are an especially effective chemistry for sur

58 The (15) N(2) labeled diazirines are appealing motifs for hyperpolarization su

59 Alkyl diazirines are frequently used in photoaffinity labeling

60 Diazirines are intrinsically smaller than benzophenones

61 Diazirines are the current gold standard for high-resolu

62 Diazirines are widely used in photoaffinity labeling (PA

63 The mechanism of cyclopropanations with diazirines as air-stable and user-friendly alternatives

64 ropyrum pernix protoglobin (ApePgb) that use diazirines as carbene precursors.

65 Using readily prepared aryl diazirines as model substrates, we demonstrate the appli

66 ative demonstrates the potential of (15) N2 -diazirines as molecular imaging tags for biomedical appl

67 Here we report the use of diazirines as practical reagents for the decarboxylative

68 The diazirine-based footprinting probe is effectively seques

69 A diazirine-based nucleoside analogue (DBN) efficiently fo

70 Photo-rapamycin was developed as a diazirine-based PAL probe for rapamycin, and the FKBP12-

71 higher photo-cross-linking efficiency than a diazirine-based photo-cross-linker, AbK, when placed at

72 Thus, PALBOX is a versatile diazirine-based photoaffinity tag for use in the develop

73 For the most active probe (11), a diazirine-based photocrosslinking analog of PreQ(1), X-r

74 rt an improved synthesis of photo-leucine, a diazirine-based photoreactive analogue of leucine, and d

75 Potential (trifluoromethyl)diazirine-based TRPML1 ion channel ligands were designed

76 The first known 3H-diazirines bearing a carbonyl group and a halogen atom o

77 ker, 3-trifluoromethyl-3-(m[125I]iodophenyl) diazirine benzoic acid ester, was incorporated into inne

78 , as well as a small-molecule chlorcyclizine-diazirine-biotin that can target and cross-link the puta

79 Thermal analysis of the diazirines by differential scanning calorimetry (DSC) pr

80 As recently reported, (15) N2 -diazirine can be hyperpolarized by the SABRE-SHEATH meth

81 However, the alkyl diazirines can preferentially label acidic amino acids a

82 aint between the conjugated residues and the diazirine carbon and a 9.0 angstrom labeling radius for

83 C-N bonds, a positive charge at the para and diazirine carbon atoms, and a negative charge at the nit

84 g comparable results to those of the matched diazirine compounds.

85 minary studies on the use of a photoreactive diazirine-containing amino acid to cross-link peptide mo

86 e application of this strategy to a (15) N2 -diazirine-containing choline derivative demonstrates the

87 We demonstrate this approach for two diazirine-containing GlcNAc analogues, and we report the

88 aturable specific binding was found with the diazirine-containing ligand.

89 This multifuctional diazirine-containing peptide was a substrate for Ste14p,

90 A tailored WOBE437-derived diazirine-containing photoaffinity probe (RX-055) irreve

91 ying upon photo-cross-linking with synthetic diazirine-containing RNA probes and quantitative proteom

92 d a panel of small molecules appended with a diazirine cross-linking moiety and an alkyne tag were pr

93 reactive and more specific than those with a diazirine cross-linking moiety.

94 MP), perfluorinated aryl azide (FAB-dUMP) or diazirine (DB-dUMP) coupled to 5-aminoallyl deoxyuridine

95 Here, using a photolyzable diazirine derivative of a novel stimulator compound, IWP

96 We synthesized a transportable diazirine derivative of D-glucose,3-deoxy-3,3-azi-D-gluc

97 inding sites on ligand-gated ion channels, a diazirine derivative of the potent intravenous anestheti

98 The reaction is initiated by a direct diazirine-diazo isomerization occurring in the active si

99 The Km value of diazirine does not depend on the ratio of nitrogenase Fe

100 eaction of the minimal photochemical reagent diazirine (DZN) with polypeptides.

101 aracterize the interactions of a second aryl diazirine etomidate derivative, TFD-etomidate (ethyl-1-(

102 olute rates of carbene/alkene additions, the diazirine exchange reaction and derived carbenes, carben

103 g the most widely used photoaffinity labels, diazirines exhibit limited compatibility with downstream

104 We find that alkyl diazirines exhibit preferential labeling of acidic amino

105 er, x-alk-16, which contains an alkyne and a diazirine, for metabolic labeling of S-palmitoylated pro

106 Finally, the (15)N(2)-diazirine from l-tyrosine was hyperpolarized by a parahy

107 uctures containing, or entirely composed of, diazirine-functionalized peptides.

108 Unfortunately, the syntheses of the diazirine-functionalized substrates have exhibited incon

109 This approach relies on an aryl-diazirine-G-clamp-modified-nucleoside (ARAGON) miRNA pro

110 clickable alkynyl group and a photoreactive diazirine group attached to the GPI glucosamine and lipi

111 cs, n-octan-1-ol geometric isomers bearing a diazirine group on either the third or seventh carbon (3

112 ecting group ("cage"), a photo-crosslinkable diazirine group, and a terminal alkyne group useful for

113 entral nitroveratryl linker and a peripheral diazirine group, resulting in diffusion of a highly reac

114 The (-CH(15) N(2) ) diazirine groups investigated here are analogues to meth

115 rsion of unprotected amino acids to terminal diazirines has been developed using phenyliodonium diace

116 The electrophilic potential of diazirines has been utilized to obtain N-substituted dia

117 al photoactivatable cross-linker, sulfo-SDA (diazirine), has yielded high-density data that facilitat

118 Although aryl(trifluoromethyl)diazirines have achieved great popularity in photoaffini

119 ic modules, whether N-chloroethyl aniline or diazirine, have reactive profiles consistent with induce

120 ines (13, 19, and 38), which rearrange to 1H-diazirines, imidoylnitrenes, and carbodiimides.

121 f 3-trifluoromethyl-3-(m-[(125)I]iodophenyl) diazirine in a mutually exclusive manner.

122 Using cholesterol analogues with a diazirine in either the 7 position of the steroid ring (

123 it has about 20-fold higher solubility than diazirine in water at 30 degrees C. trans-Dimethyldiazen

124 ss-coupling and accessing reactive, unstable diazirines in a single, unified system with high yields

125 to the wide range of substituted aryl(CF(3))diazirines in photoaffinity applications.

126 estions concerning the photoisomerization of diazirine into diazo compound and the denitrogenation in

127 omethylphenyl)pyrazolo]]-3-(trifluoromethy l)diazirine is a fipronil-based (i.e. fiprole), high-affin

128 Diazirine is reduced by nitrogenase under specific condi

129 reagent 3-trifluoro-3-(m-[(125)I]iodophenyl)diazirine, isolated, and cleaved with AspN and/or GluC,

130 es produced 10 to 25% cross-linking, whereas diazirine modified residues produced 5 to 8% cross-linki

131 culturing these cells with a cell-permeable, diazirine-modified form of GlcNAc-1-phosphate.

132 e-modified UDP-GlcNAc (UDP-GlcNDAz), and the diazirine-modified GlcNAc analog (GlcNDAz) is transferre

133 We engineered mammalian cells to produce diazirine-modified O-GlcNAc by expressing a mutant form

134 this method, cells are engineered to produce diazirine-modified UDP-GlcNAc (UDP-GlcNDAz), and the dia

135 Diazirine moieties are chemically stable and have been i

136 Two neurosteroid analogues with diazirine moieties replacing the 3-hydroxyl (KK148 and K

137 on of a new isoprenoid analogue containing a diazirine moiety that was prepared in six steps and inco

138 or ligand-coupling through free amines, 2) a diazirine moiety to capture the receptor of interest upo

139 h an alkyne, azide, maleimide, tetrazine, or diazirine moiety under redox and pH-neutral conditions.

140 e proximity of (1) H to (15) N nuclei in the diazirine moiety, (15) N T(1) times of up to (4.6+/-0.4)

141 In addition to the diazirine moiety, fluorescein and biotin groups were als

142 Ortho-propofol diazirine (o-PD) labels beta-H267, a pore-lining residue

143 n cells with reduced labeling of known alkyl diazirine off-targets.

144 y photoactivable groups based on either aryl diazirine or benzophenone chemistry, have been synthesiz

145 These compounds incorporate either a diazo, diazirine, or azido group to provide photolability in th

146 = 375 nm) of para-methoxy-3-phenyl-3-methyl diazirine (p-CH(3)OC(6)H(4)CN(2)CH(3)) produced a transi

147 We recently reported the incorporation of diazirine photo-cross-linkers onto the O-GlcNAc posttran

148 and report the development of a cyclobutane diazirine photoaffinity tag with reduced pH-dependent re

149 l metabolic labeling method to introduce the diazirine photocross-linking functional group onto O-Glc

150 tocol describes metabolic incorporation of a diazirine photocrosslinker into sialic acids in cellular

151 al approach that enables introduction of the diazirine photocrosslinker onto the O-GlcNAc modificatio

152 g 3-trifluoromethyl-3-(m-[(125)I]iodophenyl) diazirine photoincorporation than the S(-)-enantiomers.

153 Mutations at alphaE262 that reduce diazirine photomodification decreased the irreversible i

154 These are based on diazirine photoreactive groups and sulfoxide as the MS-l

155 model replication forks containing a phenyl diazirine placed at single locations, to determine the p

156 e benzophenone-derived diradical; this makes diazirines potentially more general photoaffinity-labeli

157 Diazirine potently and competitively inhibits acetylene

158 d through irradiation of their corresponding diazirine precursors followed by trapping the products i

159 ss-linking experiments demonstrated that the diazirine probe photo-cross-linked to Ste14p with observ

160 reactivity profile to rationalize why alkyl diazirine probes preferentially enrich highly acidic pro

161 From a survey of 32 alkyl diazirine probes, we use this reactivity profile to rati

162 formation of carbene 5 and isomerization to diazirine proceed from different electronically excited

163 s with diazirine reagents (especially with a diazirine reagent with a longer linker) and a moderate s

164 increased cross-linking in experiments with diazirine reagents (especially with a diazirine reagent

165 Two different photoactivated diazirine reagents provide complementary labeling inform

166 is compared with alternative schemes for the diazirine reduction.

167 While the enhanced stability of diazirines relative to their diazo isomers enables acces

168 Photo-crosslinking with diazirine revealed contacts of Pol III with DNA that are

169 e rapid process from the initially populated diazirine S(2) state (<4 ps), in competition with intern

170 ty of this approach by illustrating that the diazirine tag alone is sufficient for achieving excellen

171 ial reactivity profiles as compared to other diazirine tags in vitro and is readily incorporated into

172 ction mixtures by photocapture on a 384-spot diazirine-terminated self-assembled monolayer, and self-

173 3-(Trifluoromethyl)-3-(m-iodophenyl)diazirine (TID) is a hydrophobic inhibitor of nicotinic

174 e probe 3-(trifluoromethyl)-3-(m-iodophenyl) diazirine (TID) is a noncompetitive, resting-state inhib

175 r 3-[125I](trifluoromethyl)-3-(m-iodophenyl) diazirine (TID) to nicotinic acetylcholine receptor-rich

176 ane probe (3-trifluoromethyl-3-(m-iodophenyl)diazirine (TID)) were examined.

177 ic probe 3-(trifluoromethyl)-3-(m-iodophenyl)diazirine (TID).

178 gration reveals that photoisomerization from diazirine to diazo occurs within a few picoseconds of th

179 Furthermore, we found terminal diazirines to support hyperpolarized (1) H(2) singlet st

180 , 3'-(trifluoromethyl)-3-(m-[125I]iodophenyl)diazirine, to label proteins in the outer membrane of el

181 The photostability of the photoproduced diazirine under the conditions used precluded its rearra

182 The photostability of the photoproduced diazirine under the conditions used precluded its rearra

183 n and a 9.0 angstrom labeling radius for the diazirine upon photoactivation.

184 n, along with the preparation of a bis-(15)N diazirine validated in the late-stage isotopic labeling

185 ivity, a challenging carbene transfer from a diazirine via a putative metallo-carbene.

186 These Ir-catalysts can activate diazirine warheads through Dexter energy transfer to for

187 For the first time, a 1H-diazirine was captured as intermediate in the photoisome

188 phenyl)-5-iodopyrazolo]]-3-( trifluoromethyl)diazirine, was prepared in 10 steps from pyrazole and 3,

189 eviously neglected trifluoromethyl-aliphatic diazirines were synthesized and characterized.

190 3H-Diazirines were thermolyzed or photolyzed to generate th

191 (3-trifluoromethyl)-3-(m-[(125)I]iodophenyl)diazirine) which selectively labels proteins exposed to

192 ent of benzonitrile imine forms 3-phenyl-3 H-diazirine, which is a precursor of phenyldiazomethane an

193 4pi-electron three-membered-ring 3-methyl-1H-diazirine, which photorearranges to give methyl carbodii

194 f the labeling preferences of alkyl and aryl diazirines with individual amino acids, single proteins,

195 molecular understanding of the reactivity of diazirines with protein biomolecules.