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Science | 1970

Biological Phosphonates: Determination by Phosphorus-31 Nuclear Magnetic Resonance

Thomas Glonek; Thomas O. Henderson; Richard L. Hilderbrand; Terrell C. Myers

Advanced methods of phosphorus-31 nuclear magnetic resonance spectroscopy provided a method whereby biological phosphonates and phosphates can be determined on simple lipid fractions of biological origin. The spectra consist of two easily distinguished resonance bands; one corresponds to families of phosphonates, and the other corresponds to families of orthophosphates.


Archives of Biochemistry and Biophysics | 1972

Phosphorus-31 nuclear magnetic resonance studies of the phosphonate and phosphate composition of the sea anemone, Bunadosoma, sp

Thomas O. Henderson; Thomas Glonek; Richard L. Hilderbrand; Terrell C. Myers

Abstract Advanced methods of 31P nuclear magnetic resonance spectroscopy were used in the analysis of the phosphonate and orthophosphate components of fractions from the sea anemone Bunadosoma sp. and in the analysis of hydrolyzates from these fractions. The spectra consist of cleanly separated phosphonate and orthophosphate resonance bands which have been interpreted in some detail. Analysis of the data showed that certain orthophosphates are resistant to classical hydrolytic procedures. These same hydrolytic procedures bring about chemical alterations of the phosphonate subunits which can affect the phosphonate to phosphate ratio as classically determined.


Biochimica et Biophysica Acta | 1977

Organic phosphate binding to hemoglobin in intact human erythrocytes determined by 31P nuclear magnetic resonance spectroscopy

Wayne E. Marshall; Anthony J.R. Costello; Thomas O. Henderson; Akira Omachi

Phosphorus nuclear magnetic resonance (31P NMR) spectroscopy was used to estimate the percent of 2,3-diphosphoglycerate and ATP bound to hemoglobin in intact human erythrocytes at 37 degrees C. Binding was assessed by comparing the chemical shifts (delta) of 2,3-diphosphoglycerate and of ATP observed in intact cells with the delta values of these organic phosphates determined in model solutions closely simulating intracellular conditions, in which percent binding was directly evaluated by membrane ultrafiltration. The results showed that the percent of bound 2,3-diphosphoglycerate in intact cells varied with pH, the state of oxygenation, and 2,3-diphosphoglycerate concentration. The values ranged from 33% in cells incubated with glucose in air at an intracellular pH of 7.2 to 100% in cells incubated with inosine in N2 at a pH of 6.75. At the same 2,3-diphosphoglycerate concentration, a greater percentage of the compound appeared to be bound in erythrocytes than in the closely simulated model system. ATP was not significantly bound to hemoglobin under any condition examined, but appeared to be strongly complexed to Mg2+ inside the erythrocyte. The binding percentages for both 2,3-diphosphoglycerate and ATP in intact cells estimated by 31P NMR spectroscopy were lower than those calculated by others from individual association constants determined for the binding of different ligands to hemoglobin.


Biochimica et Biophysica Acta | 1976

Interactions between hemoglobin and organic phosphates investigated with 31P nuclear magnetic resonance spectroscopy and ultrafiltration

Anthony J.R. Costerllo; Wayne E. Marshall; Akira Omachi; Thomas O. Henderson

1. The chemical shifts (delta) of the phosphates of 2,3-diphosphoglycerate and adenosine triphosphate (ATP) were determined by phosphorus nuclear magnetic resonance (31P NMR) spectroscopy and were found to be displaced downfield following the addition of hemoglobin (3 mM) to a solution of either diphosphoglycerate (5 mM) or ATP (1 mM). 2. The binding of these compounds to hemoglobin was also determined by membrane ultrafiltration. A direct relationship was observed between the change in chemical shift ((delta delta) of the 2-P and 3-P of diphosphoglycerate and the percent diphosphoglycerate bound, when the latter was varied by altering pH, oxygenation state, or total diphosphoglycerate concentration. 3. In comparable studies with ATP binding, a linear relationship between the delta delta values of the gamma-, beta-, and alpha-P of ATP and the percent of ATP bound was not observed when the data from all of the experiments were plotted. NMR signals were not detectible in deoxyhemoglobin solutions containing 1 mM ATP but were seen in solutions containing 3.8 mM ATP. 4. The results indicate that 31P NMR spectroscopy is a promising tool for investigating organic phosphate interactions with hemoglobin.


Biochimica et Biophysica Acta | 1974

31P nuclear magnetic resonance: Application to the study of human serum high density lipoproteins

Thomas Glonek; Thomas O. Henderson; Arthur W. Kruski; Angelo M. Scanu

Abstract Highly resolved 31P nuclear magnetic resonance (31P NMR) spectra were obtained from human serum high density lipoproteins. The spectral shifts obtained were interpreted as reflecting an influence of countercations on the polar phosphate headgroups of the phospholipids found in these lipoproteins. The results indicated that 31P NMR is a potentially useful technique in the study of the structure of serum lipoproteins.


Science | 1980

2-Aminoethylphosphonic Acid Metabolism During Embryonic Development of the Planorbid Snail Helisoma

Michael V. Miceli; Thomas O. Henderson; Terrell C. Myers

In freshly laid egg masses of Helisoma sp., more than 95 percent of the phosphorus is found in alkylphosphonic acids, as determined by phosphorus-31 nuclear magnetic resonance spectroscopy. These compounds are metabolized during embryonic development, as shown by differential acid hydrolysis and experiments with phosphorus-33-labeled phosphoric acid. Further, nuclear magnetic resonance spectroscopy indicates phosphonic acid involvement in related snail families, including the schistosomal vector Biomphalaria glabrata.


Lipids | 1972

The incorporation of 2-aminoethylphosphonic acid into rat liver diacylglyceroaminoethylphosphonate

Jean M. Curley; Thomas O. Henderson

Rats intravenously administered (14C) 2-aminoethylphosphonic acid (AEP) incorporated ca. 16% of the total injected compound into liver lipids. Thin layer chromatography and selective chemical and enzymatic hydrolysis of the labeled lipids demonstrated that essentially all of the radioactivity was in one compound, diacylglycerol-AEP, the phosphonate analog of phosphatidylethanolamine. Lipids from kidneys, heart, skeletal muscle, adipose, pancreas and brain were examined and found to contain less than 2% collectively of the total injected radioactivity. The residues from the tissues contained ca. 3.2% of the total injected (14C) AEP.


Biochimica et Biophysica Acta | 1977

ATP binding to human hemoglobin in the presence and absence of magnesium ions investigated with 31P NMR spectroscopy and ultrafiltration

Anthony J.R. Costello; Wayne E. Marshall; Akira Omachi; Thomas O. Henderson

The addition of 3 mM hemoglobin to 1-10 mM ATP solutions at pH 6.75 resulted in a linear relationship between the change in chemical shift (deltadelta) of the gamma-phosphate of ATP and the percent ATP bound to hemoglobin. The data points obtained with oxyhemoglobin and deoxyhemoglobin fell on the same straight line. In the presence of 3 mM Mg2+, the delta delta decreased curvilinearly as the percent ATP bound was raised. In this case, the percent ATP bound to deoxyhemoglobin was greater than to oxyhemoglobin at the same delta delta value, indicating that the extra ATP binding occurs through groups other than phosphate.


Lipids | 1977

2-Aminoethylphosphonic acid metabolism in the rat.

Jean Curley-Joseph; Thomas O. Henderson

Time course studies of the incorporation of radioactive 2-aminoethylphosphonic acid (AEP) into the tissues of rats demonstrated that maximum incorporation into the liver lipids occurred within 12 to 30 hr after injection, compared to 2 to 3 hr for the incorporation of phosphorylethanolamine. Little incorporation of AEP was observed in the other tissues investigated (heart, lung, spleen, adipose, kidney). The AEP was incorporated to the greatest extent into 1,2-diacylglyceryl-aminoethylphosphonate (diacylglyceryl-AEP), the phosphonate analogue of phosphatidylethanolamine, with some incorporation into the lyso derivative. Diacylglycerol-AEP apparently was not further metabolized by the rat; no methylation of diacylglyceryl-AEP to phosphonolecithin was observed. Subcellular fractionation was performed on the livers of rats who received3H-AEP 12, 30, 36, and 48 hr prior to sacrifice. The greatest amount of radioactivity was recovered in the soluble fractions. Lipid extraction was performed on the subcellular fractions, and most of the radioactivity present in the lipids was found in the microsomal fraction, with the next highest recovery in the mitochondrial and nuclear fractions.


Proceedings of the National Academy of Sciences of the United States of America | 1974

Phosphate Metabolism in Intact Human Erythrocytes: Determination by Phosphorus-31 Nuclear Magnetic Resonance Spectroscopy

Thomas O. Henderson; Anthony J.R. Costello; Akira Omachi

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