Investigations on the chemistry of heparin. I. Desulfation and acetylation

Danishefsky, I.; Eiber, Harold B.; Carr, Julius J.

doi:10.1016/0003-9861(60)90621-4

Cited by 82 publications

(27 citation statements)

References 16 publications

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“…The 3-O-sulfated glucosamine structure in heparin was originally discovered in 1969 by Danishefsky et al 81 Subsequently, the presence of this particular residue has been linked to the anticoagulant activities of heparin and HS. 82,83 HS3ST activity was first reported in mouse mastocytoma cells and was speculated to be an essential activity in the generation of the antithrombinbinding site.…”

Section: B Heparan Sulfate (Hs) and Heparinmentioning

confidence: 98%

Sulfotransferases and sulfated oligosaccharides

Honke¹,

Taniguchi²

2002

Medicinal Research Reviews

111

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Structural diversity of the sugar chains attached to proteins and lipids that arises from the variety of combinations of different monosaccharides, different types of linkages, branch formation and secondary modifications, such as sulfation, possesses a large amount of biological information. A number of proteoglycans, glycoproteins, and glycolipids contain sulfated carbohydrates. Their sulfate groups provide a negative charge and play a role in a specific molecular recognition process. The sulfation of oligosaccharides is catalyzed by the Golgi-associated sulfotransferases. Recent success in molecular cloning of these sulfotransferases has brought a breakthrough in the understanding of biological function of sulfated oligosaccharides in a variety of contexts. Investigations on the relationship of sulfated oligosaccharides to human diseases including hereditary deficiency, cancer, inflammation, and infection may provide hints for curing disastrous diseases.

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Section: B Heparan Sulfate (Hs) and Heparinmentioning

confidence: 98%

Sulfotransferases and sulfated oligosaccharides

Honke¹,

Taniguchi²

2002

Medicinal Research Reviews

111

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“…Encouraged by these reports, we generated N ‐acetylated ( N ‐Ac) heparin by subjecting sodium heparinate (which is >85 % N ‐sulfated) to N ‐desulfation and N ‐acetylation and then explored the ability of various acids (e.g., H 2 SO 4 , TFA, CuCl, TMSOTf, BF 3 Et 2 O, TfOH) to produce intact HS disaccharides. We found that N ‐Ac‐heparin was efficiently hydrolyzed to give disaccharides as the major product using 1 m TfOH at 100 °C for approximately 6 h (Scheme and Figure S2).…”

Section: Resultsmentioning

confidence: 99%

“…Encouraged by these reports,w eg enerated N-acetylated (N-Ac) heparin by subjecting sodium heparinate (which is > 85 % N-sulfated) to N-desulfation and N-acetylation [9] and then explored the ability of various acids (e.g., H 2 SO 4 ,T FA, CuCl, TMSOTf, BF 3 Et 2 O, TfOH) to produce intact HS disaccharides.W ef ound that N-Ac-heparin was efficiently hydrolyzed to give disaccharides as the major product using 1m TfOH at 100 8 8Cf or approximately 6h (Scheme 1a nd Figure S2). Thec rude free disaccharide was then esterified using AcCl and MeOH, which also resulted in methylation of the anomeric hydroxy group.H ydrolysis of this methyl glycoside and acetylation of the free hydroxy groups using acetic anhydride,f ollowed by treatment with acetic anhydride/pyridine to effect N-acetylation, resulted in peracetylated disaccharide 1.…”

Section: Resultsmentioning

confidence: 99%

Expedient Synthesis of Core Disaccharide Building Blocks from Natural Polysaccharides for Heparan Sulfate Oligosaccharide Assembly

et al. 2019

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The complex sulfation motifs of heparan sulfate glycosaminoglycans (HS GAGs) play critical roles in many important biological processes. However, an understanding of their specific functions has been hampered by an inability to synthesize large numbers of diverse, yet defined, HS structures. Herein, we describe a new approach to access the four core disaccharides required for HS/heparin oligosaccharide assembly from natural polysaccharides. The use of disaccharides rather than monosaccharides as minimal precursors greatly accelerates the synthesis of HS GAGs, providing key disaccharide and tetrasaccharide intermediates in about half the number of steps compared to traditional strategies. Rapid access to such versatile intermediates will enable the generation of comprehensive libraries of sulfated oligosaccharides for unlocking the “sulfation code” and understanding the roles of specific GAG structures in physiology and disease.

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“…Uronic acid groups in mucopolysaccharides are not reduced as easily as those in hexuronic acids. Normally mucopolysaccharides are degraded partially and desulphated before the reduction of such groups is attempted in vitro (Danishefsky et al, 1960;Weissman & Meyer, 1952;Wolfrom & Juliano, 1960).…”

Section: Selective Reduction With Lithium Aluminium Hydridementioning

confidence: 99%

Studies in fluorescence histochemistry: I. The demonstration of sulphomucins*

STOWARD

1967

Journal of the Royal Microscopical Society

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SYNOPSISSulphated mucosubstances in sections of coagulant‐fixed tissue emit a variable yellow to red fluorescence after being stained with purified coriphosphine at pH 2 to 4. Unfortunately this fluorescence is sometimes indistinguishable from a similarly coloured fluorescence emitted by nuclei, oxidized sulphoproteins and some sialo‐mucins, which, however, can be eliminated more or less selectively either by (1) a preliminary Feulgen hydrolysis and condensation with N,N‐dimethyl‐m‐phenylene diamine; or (2) by pretreatment with a solution of ferric alum; or (3) by a previous methylation with methanolic thionyl chloride, followed by reduction with lithium aluminium hydride in hot dioxane and then by saponification (a sequence of reactions which, in theory but not always in practice, should remove all polyanionic groups in the tissue except sulphate groups on sulphated mucopolysaccharides); or (4), best of all, by staining sections in a very dilute solution of thiazol yellow at pH 2 after they have been stained in coriphosphine.The rationale and limitations of these methods are discussed critically.

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Investigations on the chemistry of heparin. I. Desulfation and acetylation

Cited by 82 publications

References 16 publications

Sulfotransferases and sulfated oligosaccharides

Sulfotransferases and sulfated oligosaccharides

Expedient Synthesis of Core Disaccharide Building Blocks from Natural Polysaccharides for Heparan Sulfate Oligosaccharide Assembly

Studies in fluorescence histochemistry: I. The demonstration of sulphomucins*

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