Periodate oxidation and alkaline degradation of heparin-related glycans

Fransson, Lars‐Âke; Malmström, Anders; Sjöberg, Ingrid; Huckerby, Thomas N.

doi:10.1016/s0008-6215(00)85321-5

Cited by 49 publications

(32 citation statements)

References 26 publications

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“…In the case of heparin and highly sulphated oligosaccharides the reaction mixtures contained 0.2 M sodium perchlorate in order to minimize periodatepolyanion repulsion [28]. Oxidation at pH 3.0 and 4 "C selectively destroys GlcUA in GlcNAc-containing block regions [15,16]. The extent of oxidation under the three different conditions (a -c) were essentially the same [16] despite a recent claim that citrate is consumed by periodate (J. E. Scott, personal communication).…”

Section: Degradative Methodsmentioning

confidence: 99%

“…Oxidation at pH 3.0 and 4 "C selectively destroys GlcUA in GlcNAc-containing block regions [15,16]. The extent of oxidation under the three different conditions (a -c) were essentially the same [16] despite a recent claim that citrate is consumed by periodate (J. E. Scott, personal communication). At pH 7.0 and 37 "C all non-sulphated uronic acids are oxidised.…”

Section: Degradative Methodsmentioning

confidence: 99%

“…As the most retarded fraction (A) showed low carbazole reactivity it must represent components where n = 0, i.e. GlcNAc-R derived from segments containing continuous GlcUA-GlcNAc repeats [16]. Consequently, fractions B, C and D should correspond to saccharides n = 1, 2 and 3, respectively, especially those derived from heparan sulphate 1 (Fig.…”

Section: Fragmentation Of Oxyheparan Sulphatesmentioning

confidence: 98%

“…It was recently demonstrated [15,16] that on treatment of heparan sulphate with periodate at pH 3.0 and 4 "C GlcUA associated with GlcNAc was oxidised. In contrast, the GlcUA, IdoUA and IdoUA-OSO, residues of N-sulphated regions were unaffected.…”

mentioning

confidence: 99%

“…In contrast, the GlcUA, IdoUA and IdoUA-OSO, residues of N-sulphated regions were unaffected. By alkaline degradation of oxyheparan sulphate the N-sulphated regions may be released in oligosaccharide form [16]. The present report is concerned with (a) fractionation and characterization of heparan sulphates (heparin by-products) from beef lung, (b) controlled degradation of various heparan sulphate subfractions by periodate oxidation/alkaline elimination as well as isolation and characterization of the degradation products.…”

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confidence: 99%

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Structural Studies on Heparan Sulphates

Fransson¹,

Sjöberg²,

Havsmark³

1980

European Journal of Biochemistry

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Three heparan sulphate fractions were subjected to degradation by periodate oxidation and alkaline elimination. The starting materials were one low-sulphated fraction rich in glucuronic acid and iV-acetylglucosamine (I), one fraction (IV) that was medium-suphated, contained similar proportions of iV-acetyl and iV-sulphate as well as of glucuronic and iduronic acid and one fraction (V) that was oversulphated, contained an excess of iV-sulphate and was rich in iduronic acid. Selective periodate oxidation of glucuronic acid residues within iV-acetylated regions followed by scission in alkali yielded three categories of fragments that were isolated by gel and ion-exchange chromatography. (a) iV-Acetylglucosamine-R compounds where R is the remnant of an oxidised and degraded glucuronic acid residue. (b) Medium-sized oligosaccharides, of the general structure glucosamine-(glycuronic acid-glucosamine),-R where n = 1 -4, contained largely glucuronic acid associated with glucosamines that were iV-sulphated, iV-acetylated or unsubstituted. In saccharides where n = 4 indications of an alternating arrangement of iV-sulphate and iV-acetyl groups as well as of iduronic and glucuronic acid residues were obtained. The glucuronic acid residues of the oligosaccharide fragments were susceptible to reoxidation with periodate. The smaller saccharides were not depolymerised by HNO, despite the presence of iV-sulphate groups. (c) Longer oligosaccharide fragments (n 2 5) that were highly sulphated and contained heparin-like repeating units, i. e. iduronic acid -glucosamine-iV-sulphate with ester-sulphate on both sugars. These oligosaccharides were susceptible to deaminative cleavage.

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Section: Degradative Methodsmentioning

confidence: 99%

Section: Degradative Methodsmentioning

confidence: 99%

Section: Fragmentation Of Oxyheparan Sulphatesmentioning

confidence: 98%

mentioning

confidence: 99%

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confidence: 99%

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