Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Patent
1990-10-31
1992-11-10
Schofer, Joseph L.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
526270, 526304, C08F 2400
Patent
active
051624710
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to copolymers of glycosyl amines and amides, to N-acryloyl- or methacryloyl-glycosylamines and to processes for their preparation.
BACKGROUND OF THE INVENTION
Carbohydrate structures, exposed on the surface of cells or occurring in soluble form in body fluids, are important in many biological recognition processes. To investigate such processes, low molecular weight oligosaccharides are sometimes not satisfactory. Therefore, a great deal of effort has been devoted to the development of techniques (ref. 1 to 4) for attaching oligosaccharides to larger molecules such as proteins, to give high molecular weight, multivalent conjugates. The obtained "neoglycoproteins" can be used as immunizing antigens to produce carbohydrate-directed antibodies, or as antigens in immunoassays to detect such antibodies.
However, for many applications, it is problematic to use protein conjugates. For example, in immunoassays using carbohydrate antigens, the presence of protein epitopes is highly undesirable. An alternative to proteins in these cases are water-soluble, weakly immunoreactive polymers of the polyacrylamide type. Several reports have recently appeared describing the preparation of oligosaccharide-acrylamide copolymers, both linear (ref. 5 to 14) and crosslinked (ref. 15 to 17). The general strategy for preparation of these conjugates has been to attach an olefinic group to a carbohydrate, and then copolymerize this derivative with acrylamide. The olefinic group has been introduced into the carbohydrate molecule either as an allyl glycoside at an early stage in a synthetic scheme (ref. 5-7, 9-12 and 15), by acryloylation of an amino function of a mono- or oligosaccharide derivative (ref. 8, 11, 13, 14, 17), or by other methods (ref. 16). These known techniques are, however, subject to drawback in that they cannot be directly applied to reducing di- or oligosaccharide reactants, since the reaction conditions necessary result in cleavage of interglycosidic linkages.
Few reports have appeared to date (ref. 14, 18) on the attachment of an olefinic group onto a reducing oligosaccharide. Reducing oligosaccharides of great complexity and structural variety can be isolated from natural sources such as milk (ref. 19), urine (ref. 20), and faeces (ref. 20), and also from chemical or enzymatic hydrolyzates of glycoproteins (ref. 21), glycolipids (ref. 22, 23), or lipopolysaccharides (ref. 24).
SUMMARY OF THE INVENTION
The present invention is directed to new techniques for the attachment of an olefinic group to the anomeric position of reducing saccharides. Generally, the invention is based on conversion of the saccharides used into the corresponding .beta.-glycosyl amines which are then N-acryloylated or N-methacryloylated. The N-acryloyl- or N-methacryloylglycosylamines formed are then copolymerized with acrylamide or methacrylamide to form high molecular weight, linear polymers. These new polymers are useful in for example applications involving coating antigens in ELISA assays.
According to a first aspect the invention thus provides for a copolymer of glycosyl amine and an amide, said copolymer having the general formula: ##STR3## wherein R.sup.2 is a reducing sugar residue; about 2000 kDa.
It is preferred that R.sup.2 in formula I above is a mono-, di-or oligo-saccharide residue. Particularly preferred are saccharides having 1 to 10 monosaccharide units, especially 1 to 6 units.
Although the invention is not to be construed to be limited thereto, examples of saccharides of which R.sup.2 denotes the residue are: lactose, lacto-N-tetraose, lacto-N-fucopentaose I, lacto-N-fucopentaose II, lacto-N-difucohexaose I, 2'-fucosyllactose, 3'-siallyllactose, A-tetrasaccharide, cellobiose.
In formula I above x is preferably from 1 to about 15, and m is preferably such that the molecular weight of the copolymer is from about 10 to about 500 kDa. It is preferred that R.sup.3 of formula I is hydrogen corresponding to using acrylamide as one repeating entity in the copolymer I.
In the above formula I sy
REFERENCES:
K. Kobayashi et al. Polym. J. 15 (9), 667-671 (1983).
P. Kosma, G. Schulz, and F. M. Unger, Carbohydr. Res., 180, 19-28 (1988).
R. Roy and F. Tropper, Glycoconjugate J., 5., 203-206 (1988).
E. Kallin, H. Lonn, and T. Norberg, Glycoconjugate J., 5, 145-150 (1988).
E. Kallin, H. Lonn, and T. Norberg, Glycoconjugate J. 3, 311-319 (1986).
P. Kosma, J. Gass, G. Schulz, R. Christian, and F. M. Unger, Carbohydr Res., 167, 39-54 (1987).
R. Roy, C. A. Laferriere, A. Gamian, H. J. Jennings, J. Carbohydr. Chem., 6, 161-165 (1987).
H. Paulsen and K.-W. Pflughaupt in The Carbohydrates, vol. 1B, W. Pigman and D. Horton, Eds.; Academic Press: N. Y., 1980, pp. 881-927.
A. Ya. Chernyak, A. B. Levinsky, B. A. Dmitriev, and N. K. Kochetkov, Carbohydr. Res., 128, 269-282 (1984).
A. Ya. Chernyak, K. V. Antonov, N. K. Kochetkov, L. N. Padyukov, and N. V. Tsvetkova, Carbohydr. Res., 141, 199-212 (1985).
Kallin Elisabeth
Norberg Thomas
Biocarb AB
Nagumo M.
Schofer Joseph L.
LandOfFree
Carbonhydrateacryl- and methacrylcopolymers and their manufactur does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Carbonhydrateacryl- and methacrylcopolymers and their manufactur, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Carbonhydrateacryl- and methacrylcopolymers and their manufactur will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2294577