Hybrid glycosaminoglycans synthesized by monolayers of chick embryo arterial fibroblasts

Da, Blake; He, Conrad

doi:10.1021/bi00591a033

Cited by 9 publications

(4 citation statements)

References 27 publications

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“…[44], UDP-GlcNAc [45], indole-3-glyce. [46], N-acetyl-D-glucosamine [47], and GDPmannose [44]. Besides, N-acetylgalactosamine 4-sulfate and Nacetyl-D-glucosamine share a similar structure and the difference is that N-acetylgalactosamine 4-sulfate has a sulfate at the position 4 of the ring while N-acetyl-D-glucosamine has not [38].…”

Section: Predicted Results For the Compounds With Unknown Metabolic Pmentioning

confidence: 99%

Predicting Biological Functions of Compounds Based on Chemical-Chemical Interactions

Chen

Huang

et al. 2011

PLoS ONE

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Given a compound, how can we effectively predict its biological function? It is a fundamentally important problem because the information thus obtained may benefit the understanding of many basic biological processes and provide useful clues for drug design. In this study, based on the information of chemical-chemical interactions, a novel method was developed that can be used to identify which of the following eleven metabolic pathway classes a query compound may be involved with: (1) Carbohydrate Metabolism, (2) Energy Metabolism, (3) Lipid Metabolism, (4) Nucleotide Metabolism, (5) Amino Acid Metabolism, (6) Metabolism of Other Amino Acids, (7) Glycan Biosynthesis and Metabolism, (8) Metabolism of Cofactors and Vitamins, (9) Metabolism of Terpenoids and Polyketides, (10) Biosynthesis of Other Secondary Metabolites, (11) Xenobiotics Biodegradation and Metabolism. It was observed that the overall success rate obtained by the method via the 5-fold cross-validation test on a benchmark dataset consisting of 3,137 compounds was 77.97%, which is much higher than 10.45%, the corresponding success rate obtained by the random guesses. Besides, to deal with the situation that some compounds may be involved with more than one metabolic pathway class, the method presented here is featured by the capacity able to provide a series of potential metabolic pathway classes ranked according to the descending order of their likelihood for each of the query compounds concerned. Furthermore, our method was also applied to predict 5,549 compounds whose metabolic pathway classes are unknown. Interestingly, the results thus obtained are quite consistent with the deductions from the reports by other investigators. It is anticipated that, with the continuous increase of the chemical-chemical interaction data, the current method will be further enhanced in its power and accuracy, so as to become a useful complementary vehicle in annotating uncharacterized compounds for their biological functions.

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Section: Predicted Results For the Compounds With Unknown Metabolic Pmentioning

confidence: 99%

Predicting Biological Functions of Compounds Based on Chemical-Chemical Interactions

Chen

Huang

et al. 2011

PLoS ONE

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“…This cleavage method will convert all disaccharide units of a glycosaminoglycan into disaccharides, regardless of their monosaccharide composition or sulphate substitution. Thus the selectivity obtained from the specificity of the enzymes, which often results in incomplete cleavage of the glycosidic bonds Blake & Conrad, 1979;Fukuda & Matsumura, 1976;Nakagawa et al, 1980), is complemented by complete conversions obtained in the chemical cleavage. In addition, bond cleavage by hydrazinolysis/deamination, in contrast with the bacterial eliminases, results in the preservation of the uronic acid structure and the ready identification of the structure of the disaccharide unit that was present in the original polymer.…”

Section: Discussionmentioning

confidence: 99%

The disaccharides formed by deaminative cleavage of N-deacetylated glycosaminoglycans

Shaklee¹,

Conrad²

1986

Biochemical Journal

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Chondroitin 4-sulphate, chondroitin 6-sulphate, dermatan sulphate and keratan sulphate were N-deacetylated by treatment with hydrazine and then cleaved with HNO2 at pH 4.0, and the resulting products were reduced with NaB3H4. This reaction sequence cleaved the glycosaminoglycans at their N-acetyl-D-glucosamine or N-acetyl-D-galactosamine residues, which were converted into 3H-labelled 2,5-anhydro-

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“…CS (chondroitin sulphate)-DS hybrid molecules have been reported to be present in various tissues [8][9][10][11][12][13][14][15][16]. In these hybrid molecules, GalNAc residues located in GlcA-containing moieties were sulphated at position 4 or 6; however, it is not known how the sulphation pattern of these hybrid molecules is determined.…”

Section: Introductionmentioning

confidence: 99%

“…The 35 S-labelled glycosaminoglycans formed from DSDS after the reaction with C4ST-1 (A-C) or C6ST-1 (D-F) were applied to the Superdex 30 column before (A, D) or after digestion with chondroitinase ABC (B, E) or ACII (C, F). The arrows indicate the elution position of Blue Dextran (Vo), Di-4S (Di), CS tetrasaccharide (Tet), chondroitin tetrasaccharide (Ch-Tet), CS hexasaccharide (Hex), CS octasaccharide (Oct), CS decasaccharide (Dec), CS dodecasaccharide(12) and CS tetradecasaccharide(14).…”

mentioning

confidence: 99%

Chondroitin 4-sulphotransferase-1 and chondroitin 6-sulphotransferase-1 are affected differently by uronic acid residues neighbouring the acceptor GalNAc residues

Yamada

Ohtake

Sato

et al. 2004

Biochemical Journal

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C4ST-1 (chondroitin 4-sulphotransferase-1) and C6ST-1 (chondroitin 6-sulphotransferase-1) transfer sulphate from PAPS (adenosine 3'-phosphate 5'-phosphosulphate) to positions 4 and 6 respectively of the GalNAc residues of chondroitin. We showed previously that C4ST-1 purified from rat chondrosarcoma and recombinant C4ST-1 both transfer sulphate efficiently to position 4 of the GalNAc residues of DSDS (desulphated dermatan sulphate). We report here the specificity of C4ST-1 and C6ST-1 in terms of uronic acid residue recognition around the GalNAc residue to which sulphate is transferred. When [35S]glycosaminoglycans formed from DSDS after incubation with [35S]PAPS and C4ST-1 were digested with chondroitinase ACII, a major part of the radioactivity was recovered in disaccharide fractions and the remainder distributed to tetrasaccharides and larger fractions, indicating that C4ST-1 mainly transferred sulphate to position 4 of the GalNAc residue located at the GlcA-GalNAc-GlcA sequence. Structural analysis of tetrasaccharide and larger oligosaccharide fractions indicated that C4ST-1 mainly transferred sulphate to the GalNAc residue adjacent to the reducing side of the GlcA residue. On the other hand, when [35S]glycosaminoglycans formed from DSDS after incubation with [35S]PAPS and C6ST-1 were digested with chondroitinase ACII, a major part of the radioactivity was recovered in fractions larger than hexasaccharides, indicating that C6ST-1 transferred sulphate to the GalNAc residues located in the L-iduronic acid-rich region. Structural analysis of the tetrasaccharide and larger oligosaccharide fractions indicated that C6ST-1 showed very little preference for the GalNAc residue neighbouring the GlcA residue. These results indicate that C4ST-1 and C6ST-1 differ from each other in the recognition of uronic acid residues adjacent to the targeted GalNAc residue.

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Hybrid glycosaminoglycans synthesized by monolayers of chick embryo arterial fibroblasts

Cited by 9 publications

References 27 publications

Predicting Biological Functions of Compounds Based on Chemical-Chemical Interactions

Predicting Biological Functions of Compounds Based on Chemical-Chemical Interactions

The disaccharides formed by deaminative cleavage of N-deacetylated glycosaminoglycans

Chondroitin 4-sulphotransferase-1 and chondroitin 6-sulphotransferase-1 are affected differently by uronic acid residues neighbouring the acceptor GalNAc residues

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