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Chemical Compound Review

Diazirine     diazomethane

Synonyms: Acomethylene, Azimethylene, DIAZOMETHANE, diazo-methane, CNN radical, ...
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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


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


Gene context of diazomethane


Analytical, diagnostic and therapeutic context of diazomethane


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  2. A peptidyl derivative structurally based on the inhibitory center of cystatin C inhibits bone resorption in vitro. Johansson, L., Grubb, A., Abrahamson, M., Kasprzykowski, F., Kasprzykowska, R., Grzonka, Z., Lerner, U.H. Bone (2000) [Pubmed]
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  9. GLUT1 transmembrane glucose pathway. Affinity labeling with a transportable D-glucose diazirine. Lachaal, M., Rampal, A.L., Lee, W., Shi, Y., Jung, C.Y. J. Biol. Chem. (1996) [Pubmed]
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  11. Identification of regions of the catalytic subunit of (Na-K)-ATPase embedded within the cell membrane. Photochemical labeling with [3H]adamantane diazirine. Farley, R.A., Goldman, D.W., Bayley, H. J. Biol. Chem. (1980) [Pubmed]
  12. Synthesis of the 2-amino-4-phosphonobutanoic acid analogues (E)- and (Z)-2-amino-2,3-methano-4-phosphonobutanoic acid and their evaluation as inhibitors of hippocampal excitatory neurotransmission. Kroona, H.B., Peterson, N.L., Koerner, J.F., Johnson, R.L. J. Med. Chem. (1991) [Pubmed]
  13. 2-(3-Methyl-3H-diaziren-3-yl)ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate: a derivative of the stereoselective general anesthetic etomidate for photolabeling ligand-gated ion channels. Husain, S.S., Ziebell, M.R., Ruesch, D., Hong, F., Arevalo, E., Kosterlitz, J.A., Olsen, R.W., Forman, S.A., Cohen, J.B., Miller, K.W. J. Med. Chem. (2003) [Pubmed]
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  17. Reactions of diazomethane with glycerolipids in the presence of serum or inorganic salts. Schmid, P.C., Schmid, H.H. Lipids (1994) [Pubmed]
  18. Diffusion through narrow pores: movement of ions, water and nonelectrolytes through track-etched PETP membranes. Rostovtseva, T.K., Bashford, C.L., Alder, G.M., Hill, G.N., McGiffert, C., Apel, P.Y., Lowe, G., Pasternak, C.A. J. Membr. Biol. (1996) [Pubmed]
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