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Characterization of two glucuronic acid-containing glycosphingolipids in larvae of the green-bottle fly, Lucilia caesar.

Two glucuronic acid-containing glycosphingolipids were purified from larvae of the green-bottle fly, Lucilia caesar by DEAE-Sephadex and Iatrobeads column chromatography. Structures of these acidic glycolipids, glycolipids X and Y, were elucidated by means of sugar analysis, permethylation, enzymatic hydrolysis, negative-ion fast atom bombardment mass spectrometry, and NMR studies. Glycolipid X was determined to have the following structure: GlcA beta 1-3Gal beta 1-3GalNAc alpha 1-4 GalNAc beta 1-4 GlcNAc beta 1-3Man beta 1-4Glc beta 1-1 ceramide. The other acidic glycolipid, glycolipid Y contains a phosphoethanolamine residue linked through the 6-hydroxy group of the N-acetyl-glucosamine unit of glycolipid X. The ceramide moieties were composed of saturated fatty acids (16:0-22:0) and tetradeca- and hexadeca-4-sphingenines. Based on the structural similarity of the ceramide moieties it appears likely that glycolipid X is an intermediate from which glycolipid Y is synthesized by addition of a phosphoethanolamine residue.

Animals↗

Oxidation of 7-ethoxycoumarin and conjugation of umbelliferone by intact, viable epidermal cells from the hairless mouse.

Intact, viable (greater than 80%) epidermal cells were isolated from the hairless mouse. These cells metabolized 7-ethoxycoumarin (7-EC) to umbelliferone ( UMB ) (3 pmol/min/10(6) cells) and UMB to the sulfate and glucuronide conjugates (1 pmol/min/10(6) cells). The rate of oxidation in intact cells compared well with that in disrupted cells with added NADPH, but conjugation proceeded more rapidly in disrupted cells with added cofactors, due to a combination of "activation" of the UDP-glucuronosyltransferase, and to a limitation of activity by the concentration of UDP-glucuronic acid in the intact cells. Pretreatment of the animals with 5,6-benzoflavone resulted in a 5-fold increase in the rate of oxidation, and a 2-fold increase in both the rate of conjugation and the intracellular concentration of UDP-glucuronic acid. UDP-glucuronic acid concentration in isolated cells increased during incubation with glucose, and was regenerated to a steady-state concentration on incubation of cells with UMB . Pretreatment of animals with 5,6-benzoflavone decreased the percentage of metabolite conjugated (from 30% to 15%), whereas adding an inhibitor of oxidation, ellipticine, to cells isolated from pretreated animals, increased the percentage of metabolite conjugated (from 15% to 40%). Sulfation of UMB was almost undetectable, except at very low concentrations (less than 10 nM) of substrate. Thus, glucuronidation of UMB in epidermal cells may be limited by UDP-glucuronic acid availability; sulfation in the epidermis may contribute little to the conjugation of UMB ; and greater than 70% of the products of 7-EC oxidation in the skin may remain unconjugated.

Animals↗

Identification of a hydroxylamine glucuronide metabolite of an oral hypoglycemic agent.

Glucuronides of piperazine hydroxylamines are rarely reported in the literature, and even more rarely are their structures unambiguously identified. One major metabolite was detected by liquid chromatography/mass spectrometry-radioactivity in urine from monkeys treated with the aryl piperazine oral hypoglycemic agent 9-[(1S,2R)-2-fluoro-1-methylpropyl]-2-methoxy-6-(1-piperazinyl) purine hydrochloride (1). The mass spectrum of this metabolite indicated that it was both monooxygenated and glucuronidated on the piperazine ring. Possible structures included the N- or O-glucuronic acid conjugates of a carbinolamine, hydroxylamine, or N-oxide. Treatment with beta-glucuronidase gave a monooxygenated derivative of the parent compound. 1H NMR analysis of either the glucuronic acid conjugate or the monooxygenated product provided insufficient evidence to unambiguously determine their structures. Incubation of 1 with pig liver microsomes resulted in formation of the same monooxygenated derivative derived from beta-glucuronidase treatment of the glucuronide metabolite. This in vitro system was used to generate sufficient material for analysis by 13C NMR, and the metabolite was identified as a hydroxylamine derivative 2. Incubation of the hydroxylamine with monkey liver microsomes and uridine diphospho-5'-glucuronic acid gave the same glucuronic acid conjugate as that observed in monkey urine. 13C NMR analysis of this biosynthetic product led to its unequivocal structure assignment as the O-glucuronic acid conjugate of the hydroxylamine 3.

Administration, Oral↗

Cyclical changes in the carbohydrate composition of dog endometrium.

In the first part of prooestrus glucuronic acid could not be detected, but small amounts of glucose, fructose, inositol and sorbitol were found. When progesterone was formed a small amount of glucuronic acid could be observed and sorbitol had disappeared. During the first weeks of metoestrus the amounts of fructose and glucose increased gradually, but those of glucuronic acid remained low. When more progesterone and pregnanedione were found in the endometrium the amounts of glucuronic acid began to increase and the highest values were reached in anoestrus. During the last days of anoestrus a sudden change in the carbohydrate composition of the endometrium occurred: glucuronic acid and fructose could no longer be detected, the amounts of glucose and inositol decreased and sorbitol was found. These findings show that next to the cyclical ovarian events, there is a cyclical change in te carbohydrate composition of dog endometrium.

Animals↗

Altered acetaminophen disposition in fed and food-deprived rats after acute ethanol administration.

The effects of acute ethanol administration and resulting redox changes on the hepatic glucuronidation of acetaminophen were studied in male rats, either fed or deprived of food for 24-72 hr. Regardless of the animal's nutritional status, one of the primary effects of acute ethanol administration in vivo is an increase in hepatic NADH production, usually resulting in an increased intracellular NADH/NAD ratio. Inasmuch as NAD-requiring reactions, such as the conversion of UDP-glucose to UDP-glucuronic acid, could be impaired by such redox changes, the subsequent conjugation of drugs with glucuronic acid may be decreased after ethanol administration. To test this hypothesis, the effects of ethanol on the disposition of acetaminophen (200 mg/kg, ip), a drug excreted primarily as glucuronide and sulfate conjugates in the rat, were studied. In fed rats, administration of 2 g of ethanol per kg produced minimal redox changes, and no significant alterations in hepatic UDP-glucose or UDP-glucuronic acid concentrations. Consequently, no inhibition of acetaminophen-glucuronide formation was observed. However, after at least 24 hr of food deprivation, hepatic UDP-glucuronic acid and acetaminophen-glucuronide concentrations were significantly depressed by ethanol. These results suggest that the effect of ethanol on glucuronide formation in vivo depends on the nutritional state of the animal. In fed rats, homeostatic mechanisms act to prevent any redox-mediated alterations in glucuronide conjugation. However, in food-deprived animals, such compensatory mechanisms are apparently no longer operative, and acetaminophen glucuronidation is inhibited by ethanol administration.

Acetaminophen↗

Uridine diphosphate glucose dehydrogenase from cornea and epiphysial-plate cartilage.

1. UDP-glucose dehydrogenase (EC 1.1.1.22) was extracted from epiphysial-plate cartilage of newborn pigs and from whole bovine corneas. 2. Formation of UDP-glucuronic acid was demonstrated by radioautography after separation of the sugar nucleotides by paper chromatography or t.l.c.: in these conditions a radioactive glucuronic acid spot also appears. 3. UDP-xylose prevented the formation in the incubation mixture of both UDP-glucuronic acid and free glucuronic acid. 4. In both tissues the dependence of the enzyme activity on pH and the K(m) values for UDP-glucose and NAD(+) were determined. 5. Inhibition by UDP-xylose with respect to UDP-glucose was investigated. The plots of 1/v versus 1/[UDP-glucose], and of percentage inhibition versus UDP-xylose concentration and the Hill coefficient showed that a co-operative effect existed between UDP-xylose-binding sites. 6. The physiological meaning of the different affinities of cartilage and cornea enzymes for UDP-xylose is discussed and related to the different glycosaminoglycan contents of the two connective tissues studied.

Alcohol Oxidoreductases↗

The influence of dietary protein on ascorbic acid metabolism in rats.

1. d-Glucuronolactone reductase, l-gulonolactone oxidase, uronolactonase, dehydroascorbatase, l-gulonate dehydrogenase and l-gulonate decarboxylase have been measured in the tissues of rats fed on diets containing variable amounts of protein. Rats fed on a protein-free or a 2% casein diet for 15 days showed a marked decline in the activities of d-glucuronolactone reductase, l-gulonolactone oxidase, uronolactonase and dehydroascorbatase in the liver, and no change in l-gulonate dehydrogenase and l-gulonate decarboxylase activities in the kidney when compared with rats fed on diets containing 9%, 18% or 25% casein. Giving diets containing 60% or 88% casein to rats did not appreciably alter the activities of uronolactonase, dehydroascorbatase, l-gulonate dehydrogenase and l-gulonate decarboxylase, but inhibited considerably the activities of d-glucuronolactone reductase and l-gulonolactone oxidase in the liver, resulting in decreased synthesis of ascorbic acid. 2. Rats fed on a 25% casein diet showed maximal weight gain, higher tissue reserve of ascorbic acid and higher urinary excretion of both ascorbic acid and glucuronic acid when compared with rats fed on diets containing lower or higher amounts of protein.

Alcohol Oxidoreductases↗

Characterization of Gla(KP), a UDP-galacturonic acid C4-epimerase from Klebsiella pneumoniae with extended substrate specificity.

In Escherichia coli and Salmonella enterica, the core oligosaccharide backbone of the lipopolysaccharide is modified by phosphoryl groups. The negative charges provided by these residues are important in maintaining the barrier function of the outer membrane. In contrast, Klebsiella pneumoniae lacks phosphoryl groups in its core oligosaccharide but instead contains galacturonic acid residues that are proposed to serve a similar function in outer membrane stability. Gla(KP) is a UDP-galacturonic acid C4-epimerase that provides UDP-galacturonic acid for core synthesis, and the enzyme was biochemically characterized because of its potentially important role in outer membrane stability. High-performance anion-exchange chromatography was used to demonstrate the UDP-galacturonic acid C4-epimerase activity of Gla(KP), and capillary electrophoresis was used for activity assays. The reaction equilibrium favors UDP-galacturonic acid over UDP-glucuronic acid in a ratio of 1.4:1, with the K(m) for UDP-glucuronic acid of 13.0 microM. Gla(KP) exists as a dimer in its native form. NAD+/NADH is tightly bound by the enzyme and addition of supplementary NAD+ is not required for activity of the purified enzyme. Divalent cations have an unexpected inhibitory effect on enzyme activity. Gla(KP) was found to have a broad substrate specificity in vitro; it is capable of interconverting UDP-glucose/UDP-galactose and UDP-N-acetylglucosamine/UDP-N-acetylgalactosamine, albeit at much lower activity. The epimerase GalE interconverts UDP-glucose/UDP-galactose. Multicopy plasmid-encoded gla(KP) partially complemented a galE mutation in S. enterica and in K. pneumoniae; however, chromosomal gla(KP) could not substitute for galE in a K. pneumoniae galE mutant in vivo.

Amino Acid Sequence↗

Reduction of myocardial infarct size in vivo by carbohydrate-based glycomimetics.

One of the foremost mechanisms involved in the pathogenesis of myocardial reperfusion injury is the adhesion of neutrophils within the myocardium. The initial neutrophil-endothelial cell interactions are mediated by the selectin family of adhesion molecules. Blockade of this group of adhesion molecules, through the use of synthetic carbohydrate analogs to the selectin ligand sialyl Lewisx and glycomimetics, has been beneficial in reducing neutrophil influx and infarct size. In the present study, glycyrrhizin (GM1292), a natural structural glycomimetic, was analyzed for the ability to decrease myocardial infarct size after regional myocardial ischemia/reperfusion. To determine the structural requirements for optimal cardioprotective activity, two additional compounds related to glycyrrhizin, GM3290 and GM1658 (glycyrrhetinic acid), were studied. The molecular structures of the latter two compounds differ in the number of glucuronic acid residues in their respective molecules. Open-chest, anesthetized rabbits were subjected to 30 min occlusion of the left coronary artery followed by 5 hr of reperfusion. Vehicle or glycomimetic (10 mg/kg/hr) was administered intravenously immediately before the onset of reperfusion and every hour during the reperfusion period. Myocardial infarct size in rabbits treated with GM1292 (two glucuronic acid residues) and GM3290 (one glucuronic acid residue) was reduced significantly when compared with vehicle-treated animals (P < .05). GM1658, which lacks glucuronic acid residues, did not provide a protective effect in vivo. The data suggest that GM1292 and GM3290, which contain carbohydrate moieties, are effective in reducing the degree of myocardial injury after an acute period of ischemia/reperfusion.

Animals↗

Rodent and ruminant ingestive response to flavonoids in Euphorbia esula.

Euphorbia esula, common name leafy spurge, was chemically evaluated for aversive phytochemicals that appear to minimize herbivory by rodents and cattle. A middle-layer extract elicited food aversions in rats as did the petroleum ether extract of the initial methanol extract. Kaempferol-3-0-beta-glucuronic acid and quercetin-3-0-beta-glucuronic acid were separated and identified from the middle-layer residue. This study is the first report of quercetin-3-0-beta-glucuronic acid in leafy spurge. Together these flavonoidal glucosides were mildly aversive to rats but showed less aversive activity when tested separately. The middle-layer extract produced no aversive response from cattle, while the petroleum ether extract elicited strong aversions in cattle. Flavonoidal compounds from leafy spurge that were aversive to rats, a monogastric mammal, were not aversive to cattle, a ruminant. Microbial degradation of the compounds before they reach the intestines and are absorbed into the bloodstream is likely a key advantage for cattle compared to rats.

Animals↗

Metabolism of benzo[A]pyrene in hamster embryo cells. Effect of the concentration of benzo[A]pyrene on its metabolism.

The metabolism of benzo[a]pyrene (BP) by hamster embryo cells was studied. The production of water-soluble metabolites, shown to be conjugates with glucuronic acid, depended on BP concentration. With increased BP concentration the amount of glucuronic acid conjugates increased, but the proportion of conjugates in BP or its metabolites present in the medium decreased. The metabolites extracted with ethylacetate were trans-7,8-dihydrodiol-BP (7,8-dihydrodiol) and trans-9,10-dihydrodiol-BP (9,10-dihydrodiol), but large peaks of phenolic metabolites were found by high pressure liquid chromatography (HPLC) after digesting the medium with beta-glucuronidase. Therefore, BP is metabolized to oxygenated forms, and of these, most of the phenolic metabolites and parts of the dihydrodiols are conjugated with glucuronic acid. The proportions of dihydrodiols to phenols, estimated by HPLC after beta-glucuronidase digestion, decreased when the BP concentration was decreased. The results suggest that dihydrodiols are less readily glucuronidated than phenols and so may be metabolized further to metabolites other than glucuronic acid conjugates.

Animals↗

Studies of the catalytic mechanism of microsomal UDP-glucuronyltransferase. Alpha-glucuronidase activity and its stimulation by phospholipids.

The rate at which a specific, purified form of microsomal UDP-glucuronyltransferase (designated as the GT2P type of this enzyme) catalyzes the hydrolysis of UDP-glucuronic acid was measured with pure, delipidated enzyme and enzyme reconstituted with different lysophosphatidylcholines. This activity of the GT2P type of UDP-glucuronyltransferase is referred to as alpha-glucuronidase activity. For delipidated enzyme, the rate of hydrolysis of UDP-glucuronic acid catalyzed by GT2P extrapolated to infinite concentrations of UDP-glucuronic acid was 1 X 10(-9) mol/min/mg of protein. This compares with a rate of glucuronidation of p-nitrophenol of 96 X 10(-9) mol/min/mg of enzyme, for delipidated enzyme. Addition of oleoyl- or myristoyllysophosphatidylcholine to GT2P did not affect the alpha-glucuronidase activity significantly. This activity was stimulated, however, in the presence of compounds that bind at the aglycone site but that do not undergo glucuronidation. alpha-Glucuronidase activity extrapolated to infinite concentration of UDP-glucuronic acid was 4.0 X 10(-9) mol/min/mg for delipidated enzyme assayed in the presence of less than saturating concentrations of p-nitrophenyl phenyl ether. Moreover, when the aglycone site of GT2P was occupied by ethers, the alpha-glucuronidase activity of this enzyme was enhanced by addition of phospholipids to delipidated enzyme. The extent of activation of the alpha-glucuronidase activity of GT2P, when the aglycone site was occupied, depended on the acyl chain of the lipid added to delipidated enzyme. These data indicate that the GT2P form of UDP-glucuronyltransferase catalyzes the hydrolysis of UDP-glucuronic acid at a significant rate and that lysophosphatidylcholines can influence this rate.

Animals↗

[Physiopathological effects of feeding heated oils to rats].

1. Reproduction tests were carried out in rats receiving diets containing 10 p. 100 fresh or heated linseed oil (L) or 20 p. 100 fresh or heated rapeseed (Cz) or canbra (Cb) oils. These oils were heated either at 275 degrees C (12 hours, under nitrogen), or at 200 degrees C (100 hours or 60 X 30 minutes, exposed to the air). With L-275, we observed in the young rats a very important perinatal mortality and an hepatic hypertrophy with steatosis. With L-200, the mortality was lower, but the body growth of surviving young rats was slower and their liver were enlarged. With Cz-275 and Cb-275, the results were qualitatively identical, but less important that with L-275. With Cz-200 and Cb-200, a slowing down of the body growth and an enlargement of the liver were observed. With all the heated oils, cyclic monomers were detected in liver lipids of young rats before weaning. 2. The detoxification mechanisms of components formed during heating of the oils were studied in the weaned rat. We noted that a diet containing 10 p. 100 heated linseed oil markedly increased the urinary excretion of hippuric acid and mainly of glucuronic acid as compared to the results obtained with a 10 p. 100 fresh oil diet. Kinetics of excretion of conjugated glucuronic acid shows that there are two phases: a phase of fast increase of excretion (appearance of the detoxification system), then a phase where this increase was much lower. The authors draw some practical conclusions from their whole work.

Animals↗

Purification and characterization of a catalytically active human liver UDP-glucuronosyltransferase expressed as a fusion protein in E. coli.

The purification and the characterization of functional human liver UDP-glucuronosyltransferase 2B4 produced as a Staphylococcus aureus protein A fusion protein in E. coli are described. The purified fusion protein was able to catalyze the glucuronidation of hyodeoxycholic acid, the major substrate described for this isoform to date. The effects of the amount and the nature of the phospholipids upon reconstitution into phospholipid micelles were investigated. Apparent determined Km values for hyodeoxycholic acid and UDP-glucuronic acid were 0.55 and 0.43 mM, respectively. Moreover, photoaffinity labelling of the fusion protein with a photoactivatable analog of UDP-glucuronic acid strongly suggested that this recombinant protein exhibited similar binding properties as the microsomal protein, which emphasizes its use for further structural analyses.

Affinity Labels↗

The composition and physicochemical properties of hyaluronic acids prepared from ox synovial fluid and from a case of mesothelioma.

1. Materials containing hyaluronic acid have been prepared by filtration (Ogston & Stanier, 1950) from ox synovial fluid and from a protein-rich human mesothelioma fluid. The ox material has been deproteinized by treatment with chloroform and pentanol and by gradient elution on DEAE-Sephadex; several fractions were obtained by the latter method. These materials can be stored in solution at -20 degrees without change of properties. The ox material contained 21% of protein; all other preparations contained less than 6% of protein. 2. The two materials have been compared by sedimentation and viscosity and shown to be closely similar. Treatment of the ox material with neuraminidase caused no change in its viscosity behaviour. 3. Information about the molecular configuration of the ox material has been obtained from measurements of light-scattering and viscosity. The results, though consistent with a highly extended configuration, are not consistent with a linear random-coil configuration. It is tentatively suggested that the structure may have some degree of branching and of cross-linking, which give it a rigidity with respect to expansion of the molecular domain that would not be possessed by a random coil. 4. The deproteinized material recovered from DEAE-Sephadex, though polydisperse, showed unchanged average molecular weight; however, the average radius of gyration was greater than before this treatment. 5. Acidification to approx. pH3 resulted in a contraction of the structure, with only a slight degree of expansion when the pH was restored to 6.8-7.0. 6. Measurements of optical rotatory dispersion qualitatively support a structure less simple than a linear random coil. 7. Colloid osmotic pressures of mixed solutions of bovine serum albumin and of hyaluronic acid prepared by filtration from ox synovial fluid have been measured. The results agree approximately with those of Laurent & Ogston (1963) but are in quantitative disagreement with the partition measurements of Ogston & Phelps (1960). The relationships between thermodynamic quantities in a quaternary system of electrolytes are discussed in Appendix 2. 8. Refractometric measurements have been made in connexion with light-scattering measurements, as the basis for a convenient method of determining the concentrations of solutions of hyaluronic acids, and to measure the partition of sodium chloride in dialysis experiments. The theory of the last use is discussed in Appendix 1. 9. Sedimentation measurements on the ox preparation have been made up to a concentration of 1.4x10(-2)g./ml. The form of the sedimentation coefficient-concentration relationship is discussed. The value of the sedimentation coefficient at higher concentration is the basis of an illustration of the likely effect of hyaluronic acid on the flow of water through narrow channels in connective tissue. 10. Available colorimetric methods have been shown to give low estimates for glucuronic acid when applied to highly polymerized materials, as compared with estimates by decarboxylation. A spectrophotometric titration with cetylpyridinium bromide has been shown to give estimates of carboxyl groups that agree well with those of decarboxylation when applied to preparations of hyaluronic acid under suitable conditions; the results are not affected by the presence of protein. 11. Estimates of glucosamine (Ogston, 1964) have been found to be low compared with those of total acetyl, independently of the presence of protein. The magnitude of the discrepancy is characteristically different for preparations from ox synovial fluid and from mesothelioma. 12. Sialic acid was estimated in several preparations. It is likely that this forms part of the protein. 13. Analyses of preparations for total nitrogen, amino acids, total acetyl, glucuronic acid (by decarboxylation) and ash account for at least 95.7% of the dry weight in terms of N-acetylglucosaminyl, glucuronyl, protein and metal ions. Previously published analyses of hyaluronic acids are reviewed. 14. The estimated molar ratios of glucuronic acid to glucosamine were all significantly greater than unity. 15. The analytical results are interpreted as agreeing with the physicochemical measurements in suggesting a more complex structure, for at least some hyaluronic acids, than that of an alternate linear copolymer in random-coil configuration.

Animals↗

Glycoconjugates as noninvasive probes of intrahepatic metabolism: pathways of glucose entry into compartmentalized hepatic UDP-glucose pools during glycogen accumulation.

Recent studies have questioned the efficiency with which administered glucose generates hepatic glycogen through the direct nonrecycling route compared with the indirect route from glucose recycled through glycolysis followed by gluconeogenesis. Using fasted and refed rats, we examined the relative access of infused [1-3H]- and [U-14C]glucose by way of these two pathways to liver glycogen and to hepatic glucuronic acid, the latter recovered from the urine as the glucuronide conjugated with administered acetaminophen. In fasted animals and during early refeeding, extensive dilution of administered [3H]- and [14C]glucose recovered in glycogen showed that 60-70% of the labeled glucose had undergone recycling by the indirect route. As refeeding progressed with substantial glycogen deposition, the contribution of the recycling pathway to glycogen and glucuronic acid diminished considerably. Thus, there is a shift in pathways of hepatic glucose utilization as liver glycogen accumulates. Consequently, the ratio of 3H/14C in glucuronic acid was closely correlated with the glycogen content of the liver at sacrifice, indicating that this ratio may prove useful as a noninvasive indicator of liver glycogen concentration. Since glycogen and glucuronic acid are derived by single reactions from UDP-glucose, they should show a common labeling pattern with 3H and 14C under various nutritional conditions. However, detailed analysis of their labeling patterns showed a striking divergence, implying that there must be compartmentation of the UDP-glucose pools leading to each of these end products, either because they are made in separate compartments within the same cell or because each is made in different hepatocyte populations. We favor the former explanation because galactose secreted in glycoproteins shows 3H and 14C labeling patterns similar to those of glucuronic acid conjugated with acetaminophen, and both of these conjugations occur in the endoplasmic reticulum of the liver, whereas most glycogen is present in the cytosol.

Animals↗

Calcium- and hydroxyapatite-binding properties of glucuronic acid-rich and iduronic acid-rich glycosaminoglycans and proteoglycans.

This study describes the interaction of a small chondroitin sulphate proteoglycan and the glycosaminoglycans chondroitin 4-sulphate, dermatan sulphate and heparan sulphate with hydroxyapatite. All macromolecules possessed a high affinity, with the iduronic acid-rich dermatan sulphate and heparan sulphate displaying higher adsorption maxima than the glucuronic acid-rich chondroitin 4-sulphate. At similar concentrations, dermatan sulphate produced a 30% inhibition of hydroxyapatite-induced crystal growth, whilst chondroitin 4-sulphate yielded 50% inhibition. Estimation of the calcium binding capacity of these glycosaminoglycans using equilibrium dialysis indicated that chondroitin 4-sulphate bound five times more calcium than dermatan sulphate at a calcium concentration similar to that of serum. The data indicate a possible important role for chondroitin 4-sulphate in dentinogenesis where it is the dominant glycosaminoglycan, since it could act as a capture point for calcium ions during mineralisation, with the leucine-rich domain of its parent proteoglycan acting as anchor points to type I collagen.

Adsorption↗

Thin-layer chromatography of hyaluronate oligosaccharides.

Odd- and even-numbered hyaluronate oligosaccharides with N-acetylglucosamine, glucuronic acid, or 4,5-unsaturated glucuronic acid at their nonreducing ends were separated by thin-layer chromatography, using silica gel and a solvent system of isopropanol-water (66 : 34) containing 0.05 M NaCl. In the isopropanol system, small amounts of electrolytes were necessary for the resolution of each oligosaccharide.

Acetylglucosamine↗