Disease relevance of diazomethane

• A photo-reactive diazirine derivative was attached to the 2-thiocytidine residue at position 32 of tRNA(Arg)I from Escherichia coli [1].
• Z-RLVG-CHN(2), in which the reactive carboxyterminal diazomethane was substituted by nonreactive groups [-OH, -NH(2), or -N(CH(3))(2)], resulted in peptidyl derivatives, which, in contrast to Z-RLVG-CHN(2) and cystatin C, inhibited neither cysteine proteinases nor bone resorption [2].
• The phospholipid was converted by diazomethane treatment to another active lipid that caused short-term hypotension, but not platelet aggregation, rather it inhibited the aggregation of rabbit heparinized platelets induced by platelet-activating factor [3].
• Changes in the distribution of beta-adrenoceptors (beta ARs) in the plasma membrane and the light vesicle fractions of rat liver during different phases of sepsis were studied using [3H]dihydroalprenolol binding and photoaffinity labeling with [125I]iodocyanopindolol diazirine [4].

High impact information on diazomethane

• Methylation with diazomethane of the carboxyl groups in the pyruvate moiety of agarose completely abolishes SAP binding to agarose [5].
• The cathepsin L of HPC-YP proved more resistant toward leupeptin than did liver cathepsin L. On the other hand, the former was more sensitive than the latter toward the diazomethane inhibitors, Z-Phe-Phe-CHN2 and Z-Phe-Ala-CHN2 [6].
• The fraction containing the acids was analyzed by capillary gas chromatography and by gas chromatography-mass spectrometry after esterification with diazomethane; the neutral fraction was analyzed similarly [7].
• To identify this site, PKCdelta C1B was photolabeled with three photo-activable diazirine alcohol analogs, 3-azioctanol, 7-azioctanol, and 3-azibutanol [8].
• We synthesized a transportable diazirine derivative of D-glucose,3-deoxy-3,3-azi-D-glucopyranose (3-DAG), and studied its interaction with purified human erythrocyte facilitative glucose transporter, GLUT1 [9].

Biological context of diazomethane

• The product from the 3-thiomorpholino-1',1'-dioxide sydnonimine-stimulated enzymatic cyclization of [alpha-18O] guanosine 5'-triphosphate was esterified with diazomethane [10].
• Identification of regions of the catalytic subunit of (Na-K)-ATPase embedded within the cell membrane. Photochemical labeling with [3H]adamantane diazirine [11].
• A Horner-Emmons reaction of trimethyl N-(benzyloxycarbonyl)phosphonoglycinate with 2-(diethoxyphosphinyl)acetaldehyde gave the protected dehydroamino acids 9 and 10, which were individually subjected to the following sequence of reactions: cycloaddition of diazomethane, photoelimination of N2, and acid hydrolysis, to give 5 and 6, respectively [12].
• To locate general anesthetic binding sites on ligand-gated ion channels, a diazirine derivative of the potent intravenous anesthetic, R-(+)-etomidate (2-ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate), has been synthesized and characterized [13].
• Two different lipophilic photoreagents, [3H]adamantane diazirine and 3-(trifluoromethyl)-3-(m-[125I]iodophenyl)diazirine (TID), have been utilized to examine the interactions of blood coagulation factor Va with calcium, prothrombin, factor Xa, and, in particular, phospholipid vesicles [14].

Anatomical context of diazomethane

• Radioactive N alpha-p-nitrobenzyloxycarbonyl arginyl diazomethane was covalently bound to vacuoles [15].
• 5S rRNA carrying the photoreactive diazirine groups (referred to as the 2'-aminoribose derivative and the 5-methyleneamino derivative respectively) was reconstituted into 50S subunits or 70S ribosomes [16].
• Because of the importance of rigorous selectivity in the assay of unesterified fatty acids which are present only in trace amounts in cells and body fluids, we have investigated the diazomethane procedure in detail and reached the following conclusions: (i) When diazomethane reacts with lipid extracts in organic solvent, no ester hydrolysis occurs [17].
• Treatment of the membrane with diazomethane to reduce the negative fixed charge decreases diffusion of cations and increases that of anions; diffusion of water and neutral solutes is unaffected by methylation except in the membranes with the narrowest pores (i.e., those etched for the shortest time), in which case diffusion is reduced [18].
• Identification of hydrophobic regions of the calcium-transport ATPase from sarcoplasmic reticulum after photochemical labeling with adamantane diazirine [19].

Associations of diazomethane with other chemical compounds

• Following solvolysis, deconjugation, and methylation with diazomethane, the bile acids were identified by GC-MS of trimethylsilyl derivatives [20].
• Treatment of reaction mixtures containing Component A, 5-oxoproline, and [gamma-32P] ATP with diazomethane led to appearance of a 32P-labeled compound (found on thin layer chromatography), whose formation was significantly reduced when Component B was present [21].
• Photolysis in cyclohexane gave at least a 50% yield of the CH insertion product at a diazirine concentration of 15 mM [22].
• The first consisted of trapping the arene oxides with N-acetyl-L-cysteine to form S-conjugates, methylation of the conjugates with diazomethane, and separation of the resulting diastereomeric esters by reversed phase high performance liquid chromatography [23].
• The viability of 1,3-dipolar cycloadditions of a series of 1,3-dipolar molecules (azomethine ylide, ozone, nitrone, nitrile imine, nitrile ylide, nitrile oxide, diazomethane, and methyl azide) onto the sidewalls of carbon nanotubes has been assessed theoretically by means of a two-layered ONIOM approach [24].

Gene context of diazomethane

• The activities of cathepsin B and L towards the substrate were differentiated by use of the diazomethane inhibitor, Z-Phe-Phe-CHN2 (0.01 microM), which selectively inhibits cathepsin L at this concentration [25].
• Further evidence of the cathepsin L-like nature of this activity was provided by its high sensitivity towards the diazomethane inhibitors Z-Phe-Phe-CHN2 and Z-Phe-Ala-CHN2 and towards leupeptin [26].
• At low temperature (-70 degrees C), PCP and PCN phenyl diazomethane complexes (4 and 6, respectively) are formed upon addition of phenyl diazomethane to 1 and 2 [27].
• In the present study, a 3H-cyclosporine diazirine analogue was used to photolabel viable MDR Chinese hamster ovary cells [28].
• Fine-tuning of the release rate of both the methylating agent (diazomethane) and of O(6)-benzylguanine was accomplished by variation of the hydrolysis-sensitive acyl substituent in 5 [29].

Analytical, diagnostic and therapeutic context of diazomethane

• 3) The methyl ester of the carboxyl group of the sialic acid in gangliosides can be formed with diazomethane in methanol-ether after treatment of the gangliosides with Dowex-50 (H+ form) [30].
• This material was isolated by solvent extraction and HPLC and, following treatment with diazomethane, examined by GC/MS [31].
• Thus, protein footprinting with DZN emerges as a feasible methodology useful for mapping contact regions of protein domains involved in macromolecular assemblies [32].
• Cyclopropanation is effected by diazomethane addition followed by irradiation of the resulting pyrazoline and gives a 3:1 mixture of syn:anti isomers that can be separated by crystallization [33].
• Guinea pig lung beta-adrenergic receptors purified by affinity chromatography, ion exchange chromatography, and HPLC size exclusion chromatography or photoaffinity labeled with [125]-iodocyanopindolol diazirine displayed mobilities on sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) that corresponded to Mr = 68,000 [34].

References