scholarly journals HISTOCHEMICAL ACYLATION OF ALDEHYDES PRODUCED BY PERIODIC ACID OXIDATION

1966 ◽  
Vol 14 (7) ◽  
pp. 529-537 ◽  
Author(s):  
R. D. LILLIE

Aldehydes produced in tissue sections by periodic acid oxidation are readily acetylated or benzoylated so as to weaken or completely prevent the Schiff and other chromogenic reactions. The reactivity of acylated aldehydes to Schiff reagent is promptly restored by saponification in alcoholic potassium hydroxide solution (10-20 min, 1% KOH, 70% ethanol). Benzoylation with 5-10% benzoyl chloride in pyridine gave the promptest, most complete and consistent aldehyde blockade, which was somewhat inferior on addition of 0.5% sulfuric acid. Pyridine acetic anhydride mixtures, 25, 40 and 50% gave partial to complete blockade. Addition of 0.25-0.5% sulfuric acid did not give consistent effects. Acetic anhydride at 60°C gave partial blockade at ½-5 hr, on addition of 0.01-0.25% sulfuric acid total or subtotal blockade was achieved. Acetylation in alcohol gave inferior resutlts. Use of 25% acetic anhydride ims glacial acetic acid gave inferior results; addition of 0.25% sulfuric acid produced total to subtotal blockade at 4-5 hr. Glacial acetic acid was without appreciable blockade effect. Sulfation in 10% and 25% H2SO4/glacial acetic acid failed to blockade aldehydes. Experiments with the peracetic acid Schiff reaction for ethylene groups indicate that some proportion of enol monobenzoate may be formed, and that with the various acetylation techniques a smaller or negligible proportion of enol acetate is formed. Acetic anhydride with 0.25% H2S04 at 60° appears to form only aldehyde diacetate. Experiments with the bromination silver techniques did not give satisfactory results.

1975 ◽  
Vol 23 (1) ◽  
pp. 59-64 ◽  
Author(s):  
G Gahrton ◽  
I Olsson ◽  
A Dahlqvist

The kinetics of the periodic acid oxidation as part of the periodic acid-Schiff reaction was studied by combined microinterferometry and microspectrophotometry in micromodel systems of liver glycogen and leukocyte glycogen as well as in neutrophil leukocytes. The initial formation of Schiff-positive chromogens was more rapid in neutrophil leukocytes than in liver or leukocyte glycogen. The chromogen formation was, however, practically complete within 60 min in both neutrophil leukocytes and leukocyte glycogen, but this did not appear to be the case in liver glycogen. Differences in the rate of chromogen formation may depend on various factors such as differences in the source and treatment of the glycogen. The complete periodic acid-Schiff reaction appears to be a measure of the glycogen amount in neutrophil leukocytes and the microdroplet system of leukocyte glycogen is considered to be an appropriate model for the estimation of the glycogen amount in single neutrophil leukocytes. A mean value of 13.3 10-12 g glycogen per normal human neutrophil was found.


1951 ◽  
Vol s3-92 (20) ◽  
pp. 393-402
Author(s):  
A. G. EVERSON PEARSE

1. Oxidation of tissues with performic acid gives rise to histochemically detectable reaction products particularly in two classes of material. These are keratin and lipoids of the phosphatide class. 2. Three methods have been evolved for visualizing the effect of performic acid on cystine-containing structures; two of these (performic acid/Schiff and perfoiTnic acid/cobalt nitrate) also record the effect on lipoids. 3. An attempt has been made to elucidate the chemistry of the reactions and it is suggested that oxidation of cystine in the tissues gives rise not only to cysteic acid (alanine-beta-sulphonic) but to another acid (alanine-beta-sulphinic). The latter is responsible for the positive reaction with Schiff's solution. 4. The Schiff reaction with performic acid oxidized lipoids is due to the formation of substances giving the reactions of aldehydes. It is possible that similar groups may be produced from lipoid molecules by periodic acid oxidation and that these and not polysaccharides (1.2 glycols) are responsible for the periodic acid-Schiff reaction in such cases.


Blood ◽  
1966 ◽  
Vol 28 (5) ◽  
pp. 674-682 ◽  
Author(s):  
J. BURNS ◽  
P. B. NEAME

Abstract Stoward1 conjugated acidified solutions of salicyloyl hydrazide with the dialdehydes formed from the periodic acid oxidation of vicinal glycols in guinea pig tissue sections. The method has now been utilized, with minor modification, to demonstrate glycogen in blood and marrow cells, and it has been compared with the periodic acid-Schiff reaction and with a fluorescent acriflavine Schiff-type method. It is felt that the PA-SH method will replace the existing Schiff-type fluorescent methods and that it will prove to be a useful technic to aid in the diagnosis of blood conditions, such as acute leukemia, where PAS positivity is known to occur.


1983 ◽  
Vol 31 (7) ◽  
pp. 849-858 ◽  
Author(s):  
H Barden

Through use of oxidation and blockading reactions, chemical group precursors of aldehyde demonstrable with Schiff reaction staining were identified in the soluble lipid-free lipofuscin component of neuromelanin of human substantia nigra and in lipofuscin of human inferior olive. Aldehyde generation was implied by moderate staining after bleaching neuromelanin and oxidizing lipofuscin with potassium permanganate followed by oxalic acid. Confirmation of aldehyde generation was achieved when diminished staining followed a sulfite addition blockade obtained by replacing oxalic acid with metabisulfite or bisulfite as well as by condensation blockades obtained with phenylhydrazine or aniline without replacing oxalic acid. Vic-glycol precursors of aldehyde were demonstrated in both pigments when acetylation or bromination preceded permanganate-oxalic acid and staining was unequivocally diminished only after acetylation. Vic-glycols were also demonstrated in lipofuscin by diminished staining when acetylation preceded periodic acid oxidation. Ethylenic precursors of aldehyde were suggested in performic acid-bleached neuromelanin when the minimal staining that followed this peracid's generation of Schiff reaction-negative dihydroxy groups became greatly intensified following an additional oxidation with periodic acid. This additional oxidation converted the dihydroxys to Schiff reaction-positive aldehyde. Ethylenes in lipofuscin were indicated when bromination before performic acid reduced subsequent staining.


1974 ◽  
Vol 23 (7) ◽  
pp. 420-422
Author(s):  
Yoshiharu MATSUBARA ◽  
Yoshihito FUJIHARA ◽  
Yutaka SAKAI ◽  
Makoto SANO

1989 ◽  
Vol 42 (8) ◽  
pp. 1281 ◽  
Author(s):  
MR Grimmett ◽  
ST Hua ◽  
KC Chang ◽  
SA Foley ◽  
J Simpson

Nitration of 4-nitroimidazole in acetic anhydride/glacial acetic acid gives 1,4-dinitroimidazole. The crystal and molecular structure of this compound have been determined by direct methods. Crystals are orthorhombic; P212121, a 5.853(3), b 9.591(8), c 10.392(5) � , V 583.4(7) � 3 , Dm 1 .76 g cm-1, Dc, 1 .80 g cm-1 (Z = 4); λ 0.71069 � ; T 173 K. The structure was refined to R = 0.048 for 926 reflections [I > 2 σ(1)]. Both 2-methyl-4-nitro- and 5-methyl-4-nitro-imidazoles N-nitrate under the same conditions. When heated in solution at 100-140�C 1,4-dinitro- and 2-methyl-1,4-dinitro-imidazoles rearrange to give C-nitro isomers and some denitration products, but 5(4)-methyl-1,4(5)-dinitroimidazole failed to give identifiable products.


1963 ◽  
Vol 9 (2) ◽  
pp. 121-134 ◽  
Author(s):  
Nathan Radin ◽  
Adalbert L Gramza

Abstract Three recrystallization technics were used to fractionate five commercial cholesterol products and one artificial mixture. One technic involved the recrystallization of cholesterol from absolute ethyl alcohol, the second technic involved the recrystallization of cholesterol from glacial acetic acid, and the third technic used the dibromide derivative method. The molar absorptivities for the various crystal batches were in the range of 1610 to 1750 L. mole-1 cm.-1 at 620 mµ with a modified Liebermann-Burchard procedure. The molar absorptivities were in the range of 9,800 to 11,500 L. mole-1 cm.-1 at 560 mµ with a modified sulfuric acid-iron method. The original products and the ethyl alcohol recrystallized products showed molar absorptivities at the lower limits of the ranges, while the glacial acetic acid and dibromide derivative recrystallized cholesterol showed molar absorptivities at the higher limits of the ranges. Absorption peaks at 235 mµ for methyl alcohol solutions of the cholesterol preparations were used to estimate cholesterol impurities on the basis of 7-keto cholesterol acetate absorption values. The decrease of absorption in the ultraviolet spectral region established that impurities were removed from the cholesterol preparations studied.


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