Methods for the preparation of oligosaccharide products from polysaccharide starting materials are disclosed. The methods include: hydrolyzing a glucosamine-containing polysaccharide starting material, such as heparin or heparosan, under conditions sufficient to form an oligosaccharide intermediate (e.g., a GlcN-IdoA disaccharide intermediate or a GlcA-GlcN disaccharide intermediate), and converting the oligosaccharide intermediate to the oligosaccharide product. Conversion of the oligosaccharide intermediates to the oligosaccharide products may include one or more esterification, acylation, epimerization, protection, and deprotection steps. Preparation of higher-order oligomers is described, as well as methods for selective oligosaccharide sulfation.

A glycosaminoglycan derivative which is obtainable by a process that includes the steps of N-desulfation of from 25% to 100% of the N-sulfated residues of a glycosaminoglycan, and oxidation, by periodate at a pH of from 5.5 to 10.0, of from 25% to 100% of the 2-N-, 3-O-non-sulfated glucosamine residues, and of the 2-O-non-sulfated uronic acid residues of said glycosaminoglycan, under conditions effective to convert adjacent diols and adjacent OH/NH.sub.2 to aldehydes. The process further includes reduction, by sodium borohydride, of said oxidized glycosaminoglycan, under conditions effective to convert said aldehydes to alcohols, where the glycosaminoglycan is heparin, low molecular weight heparin, heparan sulfate or fractions thereof.

The present invention relates to a method for degrading a polysaccharide in the field of food, medicine or chemical industry. In particular, a molecular chain of the polysaccharide is broken by ozone into polysaccharides with smaller molecular weights, oligoses and/or oligosaccharides. The polysaccharides include linear or branched glycans extracted from plants, traditional Chinese medicinal materials, animals, fungi, or microorganisms and sulfated polysaccharides or esterified polysaccharides formed by sulfation or esterification thereof. As an oxidizing agent in the reaction, the ozone can be used alone or can be used under the catalysis of a base, a metal ion, hydrogen peroxide, UV light, or activated carbon to accelerate the reaction. The method for degrading the polysaccharide in the present invention uses milder reaction conditions compared to a conventional acid-catalytic degradation method, has higher reaction efficiency and a controllable reaction process, does not need to use an acid, and reduces environmental pollution.

The present invention provides an improved process for the preparation of Enoxaparin sodium. The process is simple, commercially viable and industrially advantageous.

A glycosaminoglycan derivative which is obtainable by a process that includes the steps of N-desulfation of from 25% to 100% of the N-sulfated residues of a glycosaminoglycan, and oxidation, by periodate at a pH of from 5.5 to 10.0, of from 25% to 100% of the 2-N-, 3-O-non-sulfated glucosamine residues, and of the 2-O-non-sulfated uronic acid residues of said glycosaminoglycan, under conditions effective to convert adjacent diols and adjacent OH/NH.sub.2 to aldehydes. The process further includes reduction, by sodium borohydride, of said oxidized glycosaminoglycan, under conditions effective to convert said aldehydes to alcohols, where the glycosaminoglycan is heparin, low molecular weight heparin, heparan sulfate or fractions thereof.

The present invention provides an improved process for the preparation of Dalteparin sodium. The process is simple, commercially viable and industrially advantageous.

Disclosed are a carboxylated glycosaminoglycan derivative, a preparation method therefor, and the use thereof for inhibiting tumor growth and/or metastasis.

The invention relates to N-desulfated and optionally 2-O-desulfated glycosaminoglycan derivatives, wherein at least part of the adjacent diols and OH/NH.sub.2 have been converted into the corresponding aldehyde, which aldehydes have been then reduced to the corresponding alcohol. These products are endowed with heparanase inhibitory activity and anti-tumor activity. Said glycosaminoglycan derivatives are obtained from natural or synthetic glycosaminoglycan, preferably from unfractionated heparin, low molecular weight heparins (LMWHs), heparan sulfate or derivatives thereof. The invention further relates to the process for preparation of the same and further to their use as active ingredients of medicaments, also in combination with known established drugs or treatments. The present invention further relates to a process for breaking the C.sub.2-C.sub.3 linkage of glucosamine residues of a glycosaminoglycan by oxidation of said glycosaminoglycan.

The invention relates to glycosaminoglycan derivatives, endowed with heparanase inhibitory activity and antitumor activity, bearing carboxylate groups in positions 2 and 3 of at least part of the glycosaminoglycan residues, and to the process for preparing the same. The glycosaminoglycan derivatives of the present invention are generated starting from natural or synthetic glycosaminoglycans, preferably heparin or low molecular weight heparin, optionally 2-O- and 2N-desulfated by two steps of oxidation. By the first oxidation, adjacent diols and optionally adjacent OH/NH.sub.2 of the glycosaminoglycan residues are converted to aldehydes and by the second oxidation said dialdehydes are converted to carboxylate groups. The first oxidation preferably leads to the cleavage of C.sub.2-C.sub.3 linkage of the ring of oxidable residues. The invention further relates to a process for the preparation of said glycosaminoglycan derivatives and further to their use as active ingredients of medicaments. Furthermore, the invention relates to pharmaceutical compositions comprising di/tricarboxylated heparin derivatives, as active agent.

Affinity purification of platelet-derived growth factor-binding heparan sulphate from porcine mucosa (HS6) is disclosed. Also disclosed is the use of HS6 in repair and regeneration of the skin for treating wounds, burns, ulcers and other skin injuries.