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Patent Issued for 1,2-Dideoxy-1,2-Diamino Oligosaccharides and Polysaccharides and Derivatives

August 26, 2014



By a News Reporter-Staff News Editor at Life Science Weekly -- A patent by the inventors Dekany, Gyula (Sinnamon Park, AU); Bajza, Istvan (Debrecen, HU); Bojstrup, Marie (Tastrup, DK); goston, Karoly (Telki, HU); Kroger, Lars (Hamburg, DE); Perez, Ignacio Figueroa (Copenhagen, DK); Rohrig, Christoph H. (Muhlingen, DE); Vital, Paulo (Kobenhavn V, DK); Czinege, Erzsebet (Esztergom, HU), filed on November 3, 2008, was published online on August 12, 2014, according to news reporting originating from Alexandria, Virginia, by NewsRx correspondents (see also Glycom A/S).

Patent number 8802841 is assigned to Glycom A/S (Kgs. Lyngby, DK).

The following quote was obtained by the news editors from the background information supplied by the inventors: "One of most commonly applied chemical reactions between an amino acid and a reducing sugar is the Maillard reaction. The reactive carbonyl group of the sugar interacts with the nucleophilic amino group of the amino acid resulting interesting but poorly characterized odor and flavor molecules. This reaction is the basis of the flavoring industry, since the type of amino acid determines the resulting flavor. In this the process, numerous different flavor compounds are created. Although this reaction has been used since ancient times, the reaction is named after the chemist Louis-Camille Maillard who investigated it in the 1910s..sup.1

"Related reactions are the Amadori rearrangement and the Heyns rearrangement. The Amadori rearrangement.sup.2 is an acid or base catalyzed isomerisation of the N-glycoside of an aldose or the glycosylamine to the corresponding 1-amino-1-deoxy-ketose, while during the Heyns rearrangement ketoses react with amines forming ketosylamines which further isomerise to the corresponding 2-amino-2-deoxy-aldoses. The second rearrangement was first described by Fisher.sup.3 and later further investigated by Heyns and Koch..sup.4 The Heyns rearrangement reaction was further studied by Carson's and Heyns's labs and numerous different experiments were performed using fructose and other monosaccharides as starting materials..sup.5

"Up to now the isolated yields of Heyns reactions have been moderate in most cases because this reaction suffers from a variety of problems such as competition between hydrolysis and rearrangement of the initial ketosylamines, epimer formation at position 2, separation problems, side reactions, further degradation entering into the Maillard reaction cascade etc. These difficulties caused the absence of synthetic application of this rearrangement reaction. Recently an improved method was published to increase the yield of the rearranged product from fructose..sup.6

"Experiments using oligosaccharides as a starting compound for the Heyns reaction are rarely performed and, where they are performed, the process involves the isolation of labile ketosylamine. Stutz's group did valuable work using lactulose and turanose as a starting ketose for the reaction.sup.7 isolating lactosamine and nigerosamine as products.

"To date, no oligosaccharides have been described in the literature having a reducing end structure of 1,2-dideoxy-1,2-diamino, although these compounds might be expected to be easily available by Heyns reaction of oligosaccharides characterized by a keto-hexose reducing end structural motif.

"WO2007/104311 describes a range of novel compounds having useful functionality. An aim of certain aspects of the present invention is to provide an improved route to such compounds and novel intermediates for use in such a process."

In addition to the background information obtained for this patent, NewsRx journalists also obtained the inventors' summary information for this patent: "The present invention provides novel 1,2-dideoxy-1,2-diamino oligosaccharide derivatives and methods for the preparation of these products in their free base, salt or metal-complex forms avoiding the isolation of labile ketosyl amines.

"Furthermore, the present invention provides novel methods for the transformation of the titled 1,2-dideoxy-1,2-diamino oligosaccharides into oligosaccharides containing 2-deoxy-2-amino hexose residues at their reducing end.

"The first aspect of the present invention provides 1,2-dideoxy-1,2-diamino oligosaccharides or polysaccharides in their free base, salt or metal-complexed forms.

"The first embodiment of the first aspect of the present invention provides novel 1.fwdarw.4 linked 1,2-dideoxy-1,2-diamino disaccharide derivatives in their free base, salt or metal-complexed forms.

"The second embodiment of the first aspect of the present invention provides novel 1.fwdarw.6 linked 1,2-dideoxy-1,2-diamino disaccharide derivatives in their free base, salt or metal-complexed forms.

"The third embodiment of the first aspect of the present invention provides novel 1.fwdarw.3 linked 1,2-dideoxy-1,2-diamino disaccharide derivatives in their free base, salt or metal-complexed forms.

"The second aspect of the present invention provides novel methods suitable for the preparation of 1,2-dideoxy-1,2-diamino oligosaccharides or polysaccharides and the isolation of such compounds in their free base, salt or metal-complexed forms.

"The first embodiment of the second aspect of the present invention provides novel methods suitable for the preparation of 1.fwdarw.4 linked 1,2-dideoxy-1,2-diamino disaccharides and the isolation of such compounds in their free base, salt or metal-complexed forms.

"The second embodiment of the second aspect of the present invention provides novel methods suitable for the preparation of 1.fwdarw.6 linked 1,2-dideoxy-1,2-diamino disaccharides and the isolation of such compounds in their free base, salt or metal-complexed forms.

"The third embodiment of the second aspect of the present invention provides novel methods suitable for the preparation of 1.fwdarw.3 linked 1,2-dideoxy-1,2-diamino disaccharides and the isolation of such compounds in their free base, salt or metal-complexed forms.

"The third aspect of the present invention provides methods for the preparation of 2-deoxy-2-amino oligosaccharides from 1,2-dideoxy-1,2-diamino oligosaccharides.

"The first embodiment of the third aspect of the present invention provides methods for the preparation of 1.fwdarw.4 linked 2-deoxy-2-amino oligosaccharides from 1.fwdarw.4 linked 1,2-dideoxy-1,2-diamino oligosaccharides in which the indicated 1.fwdarw.4 linkage is maintained between the reducing end sugar residue and at least one of the connected sugar residues.

"The second embodiment of the third aspect of the present invention provides methods for the preparation of 1.fwdarw.6 linked 2-deoxy-2-amino oligosaccharides from 1.fwdarw.6 linked 1,2-dideoxy-1,2-diamino oligosaccharides in which the indicated 1.fwdarw.6 linkage is maintained between the reducing end sugar residue and at least one of the connected sugar residues.

"The third embodiment of the third aspect of the present invention provides methods for the preparation of 1.fwdarw.3 linked 2-deoxy-2-amino oligosaccharides from 1.fwdarw.3 linked 1,2-dideoxy-1,2-diamino oligosaccharides in which the indicated 1.fwdarw.3 linkage is maintained between the reducing end sugar residue and at least one of the connected sugar residues.

"Further, the present invention provides for the use of 1,2-dideoxy-1,2-diamino oligosaccharides or polysaccharides in the preparation of other oligosaccharide or polysaccharide products. Such a use may be by means of conversion of 1,2-dideoxy-1,2-diamino oligosaccharides or polysaccharides to 2-amino-2-deoxy oligosaccharides or polysaccharides, and in particular a conversion of 1,2-dideoxy-1,2-diamino disaccharides to 2-amino-2-deoxy disaccharides, such as lactosamine. Further, such a use may be by means of conversion of 1,2-dideoxy-1,2-diamino oligosaccharides or polysaccharides to N-substituted 2-amino-2-deoxy oligosaccharides or polysaccharide, and in particular a conversion of 1,2-dideoxy-1,2-diamino disaccharides to N-substituted 2-amino-2-deoxy disaccharides, such as N-alkyllactosamines.

"It is further envisaged in the present invention that the 1,2-dideoxy-1,2-diamino oligosaccharides or polysaccharides may find application as medicaments, as pharmaceuticals, as diagnostic agents, in diagnostic kits, as a detergent or surfactant, or as a food additive or component of food products."

URL and more information on this patent, see: Dekany, Gyula; Bajza, Istvan; Bojstrup, Marie; goston, Karoly; Kroger, Lars; Perez, Ignacio Figueroa; Rohrig, Christoph H.; Vital, Paulo; Czinege, Erzsebet. 1,2-Dideoxy-1,2-Diamino Oligosaccharides and Polysaccharides and Derivatives. U.S. Patent Number 8802841, filed November 3, 2008, and published online on August 12, 2014. Patent URL: http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=8802841.PN.&OS=PN/8802841RS=PN/8802841

Keywords for this news article include: Peptides, Proteins, Glycom A/S, Amino Acids.

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Source: Life Science Weekly


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