A CHEMICAL PROCEDURE FOR DETERMINATION OF THE C14-DISTRIBUTION IN LABELLED D-FRUCTOSE AND OTHER KETOSES

1957 ◽  
Vol 35 (1) ◽  
pp. 7-13 ◽  
Author(s):  
Carol Brice ◽  
A. S. Perlin

A procedure is described for determining the activity of the individual carbon atoms in D-fructose labelled with C14, which is suitable for as little as 1 millimole of the sugar. The D-fructose is degraded by lead tetraacetate oxidation and the product is hydrolyzed to glycolic acid, formic acid, and D-glyceraldehyde. Glycolic acid is oxidized to formaldehyde (carbon-1) and carbon dioxide (carbon-2), and formic acid to carbon dioxide (carbon-3). D-Glyceraldehyde is degraded to carbon dioxide (carbons-4 and -5, combined) and formaldehyde (carbon-6); after reduction of a second portion of the D-glyceraldehyde to glycerol, the degradation products obtained are carbon dioxide (carbon-5) and formaldehyde (carbons-4 and -6, combined). The activity of carbon-1, -2, -3, -5, or -6 is thus determined directly, and of carbon-4 by difference in two ways. The procedure should also be applicable to C14-labelled L-sorbose. Lead tetraacetate oxidation of sedoheptulose followed by hydrolysis yields glycolic acid, formic acid, and D-erythrose. These three fragments are degraded in turn to afford a method for partial determination of the C14-distribution in samples of this important heptulose.

1957 ◽  
Vol 35 (1) ◽  
pp. 7-13 ◽  
Author(s):  
Carol Brice ◽  
A. S. Perlin

A procedure is described for determining the activity of the individual carbon atoms in D-fructose labelled with C14, which is suitable for as little as 1 millimole of the sugar. The D-fructose is degraded by lead tetraacetate oxidation and the product is hydrolyzed to glycolic acid, formic acid, and D-glyceraldehyde. Glycolic acid is oxidized to formaldehyde (carbon-1) and carbon dioxide (carbon-2), and formic acid to carbon dioxide (carbon-3). D-Glyceraldehyde is degraded to carbon dioxide (carbons-4 and -5, combined) and formaldehyde (carbon-6); after reduction of a second portion of the D-glyceraldehyde to glycerol, the degradation products obtained are carbon dioxide (carbon-5) and formaldehyde (carbons-4 and -6, combined). The activity of carbon-1, -2, -3, -5, or -6 is thus determined directly, and of carbon-4 by difference in two ways. The procedure should also be applicable to C14-labelled L-sorbose. Lead tetraacetate oxidation of sedoheptulose followed by hydrolysis yields glycolic acid, formic acid, and D-erythrose. These three fragments are degraded in turn to afford a method for partial determination of the C14-distribution in samples of this important heptulose.


1955 ◽  
Vol 33 (1) ◽  
pp. 368-373 ◽  
Author(s):  
Stewart A. Brown

A series of reactions reported previously for the degradation of glucose has been modified and extended to permit the determination of carbon-14 in each of the five carbons of a single 2 mM. xylose sample. Methyl xylopyranoside was oxidized with periodic acid giving C-3 as formic acid, and a dialdehyde which was converted to strontium methoxy-diglycolate. The purified salt was hydrolyzed to glyoxylic and glycolic acids. The glyoxylic acid was isolated as the 2, 4-dinitrophenylhydrazone (C-1 + C-2) which was decarboxylated to give carbon dioxide from C-2. The glycolic acid was oxidized by lead tetraacetate to give C-4 as carbon dioxide and C-5 as formaldehyde. The activity in C-1 was determined by difference. The method was applied to xylose-1-C14, xylose-5-C14, and a biologically synthesized xylose sample with satisfactory results. This degradation procedure is theoretically applicable to other aldopentoses and aldotetroses.


1955 ◽  
Vol 33 (3) ◽  
pp. 368-373 ◽  
Author(s):  
Stewart A. Brown

A series of reactions reported previously for the degradation of glucose has been modified and extended to permit the determination of carbon-14 in each of the five carbons of a single 2 mM. xylose sample. Methyl xylopyranoside was oxidized with periodic acid giving C-3 as formic acid, and a dialdehyde which was converted to strontium methoxy-diglycolate. The purified salt was hydrolyzed to glyoxylic and glycolic acids. The glyoxylic acid was isolated as the 2, 4-dinitrophenylhydrazone (C-1 + C-2) which was decarboxylated to give carbon dioxide from C-2. The glycolic acid was oxidized by lead tetraacetate to give C-4 as carbon dioxide and C-5 as formaldehyde. The activity in C-1 was determined by difference. The method was applied to xylose-1-C14, xylose-5-C14, and a biologically synthesized xylose sample with satisfactory results. This degradation procedure is theoretically applicable to other aldopentoses and aldotetroses.


1955 ◽  
Vol 33 (1) ◽  
pp. 62-68 ◽  
Author(s):  
B. Boothroyd ◽  
Stewart A. Brown ◽  
J. A. Thorn ◽  
A. C. Neish

A procedure based on the work of Jackson and Hudson was developed for the degradation of methyl-α-D-glucopyranoside formed from 2 millimoles of glucose. Oxidation of the glucoside with periodic acid gave C-3 as formic acid and a dialdehyde which was converted to the strontium salt of D′-methoxy-D-hydroxymethyl diglycolic acid. The purified salt was hydrolyzed to glyoxylic and glyceric acids. The glyoxylic acid was isolated as the 2,4-dinitrophenylhydrazone (C-1 + C-2); this was decarboxylated by heat to give carbon dioxide from C-2. The glyceric acid was oxidized by periodate to give C-4 as carbon dioxide, C-5 as formic acid, and C-6 as formaldehyde. This degradation permitted the determination of C14 in each position of the glucose molecule, the activity in C-1 being determined by difference. The method was applied to glucose-1-C14 and a sample of glucose labeled in all positions with satisfactory results.


1955 ◽  
Vol 33 (1) ◽  
pp. 62-68 ◽  
Author(s):  
B. Boothroyd ◽  
Stewart A. Brown ◽  
J. A. Thorn ◽  
A. C. Neish

A procedure based on the work of Jackson and Hudson was developed for the degradation of methyl-α-D-glucopyranoside formed from 2 millimoles of glucose. Oxidation of the glucoside with periodic acid gave C-3 as formic acid and a dialdehyde which was converted to the strontium salt of D′-methoxy-D-hydroxymethyl diglycolic acid. The purified salt was hydrolyzed to glyoxylic and glyceric acids. The glyoxylic acid was isolated as the 2,4-dinitrophenylhydrazone (C-1 + C-2); this was decarboxylated by heat to give carbon dioxide from C-2. The glyceric acid was oxidized by periodate to give C-4 as carbon dioxide, C-5 as formic acid, and C-6 as formaldehyde. This degradation permitted the determination of C14 in each position of the glucose molecule, the activity in C-1 being determined by difference. The method was applied to glucose-1-C14 and a sample of glucose labeled in all positions with satisfactory results.


1979 ◽  
Vol 24 (4) ◽  
pp. 479-483 ◽  
Author(s):  
Dale Allen Raines ◽  
Edward W.D. Huffman
Keyword(s):  

1983 ◽  
Vol 66 (5) ◽  
pp. 1158-1163 ◽  
Author(s):  
Ronald C Lundstrom ◽  
Linda D Racicot

Abstract The volatile amines dimethylamine (DMA) and trimethylamine (TMA) are common degradation products of TMA-oxide in marine fish- Both compounds are used as important indicators of quality in seafoods. DMA is produced along with an equimolar quantity of formaldehyde by action of an endogenous enzyme found primarily in gadoid fish. TMA is produced in fresh, but not frozen seafoods by a bacterial enzyme. The current AOAC method for determination of TMA in fish is based on the colorimetric estimation of TMA as a picrate salt. This method is not specific for TMA; ammonia, monomethylamine, and DMA also form corresponding picrate salts. Gas chromatography provides a means of separating and quantitating the individual volatile amines. A simple perchloric acid extract of fish is neutralized with potassium hydroxide and extracted with benzene. The amines are then separated by gas chromatography on a porous polymer packed column and detected by using a nitrogen-phosphorus-specific flame ionization detector. The method provides simple, rapid simultaneous quantitation of DMA and TMA, and is applicable to a wide variety of seafoods.


1957 ◽  
Vol 3 (7) ◽  
pp. 945-951 ◽  
Author(s):  
N. H. Tattrie ◽  
A. C. Blackwood

L-Erythrulose was dissimulated anaerobically by Aerobacter aerogenes PRL R4 producing acetic acid, formic acid, succinic acid, glycolic acid, ethanol, erythritol, hydrogen, carbon dioxide, and traces of acetone and 2,3-butanediol. D-Erythrose and D-threose were also dissimilated to form the same products. Resting cells metabolized the tetroses, whereas cell-free preparations were inactive. Phosphorylation of the tetroses was not found with cell-free preparations.


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