Preparation of glucosaminyl muramic acid derivatives

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 41, 536 172, 536 185, 536 186, 536124, C07H 1500

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060083336

ABSTRACT:
The present invention provides a method for the preparation of disaccharides, such as glucosaminyl muramic acids peptides and derivatives. The method includes condensing a protected muramic acid ester with a 1-organothio- or 1-fluoroglucosamine derivative in the presence of a suitable promoter to produce a protected glucosaminyl muramic acid ester. The protected glucosaminyl muramic acid ester may be used to prepare disaccharide peptides, such as N-acetylglucosaminyl-N-acetylmuramyl dipeptides, which have demonstrated immunological activity. Protected muramic acid esters and 1-organothio- or 1-fluoro-glucosamine compounds which may be employed as intermediates in the method are also provided.

REFERENCES:
patent: 4391800 (1983-07-01), Durette et al.
patent: 4395399 (1983-07-01), Ovchinnikov et al.
patent: 4545932 (1985-10-01), Takase et al.
patent: 4774231 (1988-09-01), Petitou et al.
patent: 4950645 (1990-08-01), Vosika et al.
patent: 5371202 (1994-12-01), Hasegawa
patent: 5750665 (1998-05-01), Vosika et al.
Baker et al., "Puromycin Synthetic Studies. V. 6-Dimethylamino-0-(2'-acetamido-.beta.-D-glucopyranosyl)purine," J. Organic Chemistry, 19, 1786-1792 (Jun. 1954).
Bomford et al., "The Control of the Antibody Isotype Response to Recombinant Human Immunodeficiency Virus gp120 Antigen by Adjuvants," AIDS Research and Human Retroviruses, 8(10), 1765-1771 (Oct., 1992).
Campbell et al., "Idiotype Vaccination Against Murine B Cell Lymphyoma," J. of Immunology, 145(3), 1029-1036 (Aug. 1, 1990).
Chapleur et al., "On the Reaction of 4,6,-0-Benzylidene-2-deoxypyranosides with Sodium Cyanoborohydride: Formation of 1,5-Anhydroalditols," J. Chem. Soc., Perkin Transactions I, (Issue No. 4), 703-705 (Apr. 1989).
Durette et al. (I), "Synthesis of 0-(2-acetamido-2-deoxy-.beta.-D-glucosyl)-(1->4)-N-acetylmuramoyl-L-alanyl -D-isoglutamine, the Repeating Disaccharide-Dipeptide Unit of the Bacterial Cell-Wall Peptidoglycan," Carbohydrate Research, 77, C1-C4 (Dec. 1979).
Durette et al. (II), "Bacterial Cell Wall Constituents. II. Synthesis of 0-(N-Acetyl-.beta.-muramyl-L-alanyl-D-isoglutamine)-(1->4)-N-acetyl-D-gluc osamine," Tetrahedron Letters, (Issue No. 42), 4013-4016 (Oct. 1979).
Farkas et al., "The Synthesis of 0-(2-acetamido-2-deoxy-.beta.-D-glycopyranosyl)-1->4)-N-acetylnormuramoyl- L-.alpha.-aminobutanoyl-D-isoglutamine," Carbohydrate Research, 163(1), 63-72 (Jun. 1, 1987).
Flowers et al., "The Synthesis of 2-Acetamido-3-0-(D-1-carboxyethyl)-2-deoxy-.alpha.-D-glucose (N-aceylmuramic Acid) and of Benzyl Glycoside Derivatives of 2-Amino-3-0-(D-1-carboxyethyl)-2-deoxy-D-glucose (Muramic Acid)," J. Organic Chemistry, 28, 2983-2986 (Nov. 1963).
Furuta et al., "Synthesis and Biological Activites of N -Acetylglucosaminyl-.beta.-(1->4)-N -Acetylmuramyl Tri- and Tetrapeptide Derivatives," Agricultural and Biological Chemistry, 50(10), 2561-2572 (Oct. 1986).
Gross et al., "Stereochemically Pure Derivatives of Muramic and Isomeramic Acids," Liebigs Annalen der Chemie, 1986(1), 37-45.
Guinand et al., "Enzymatic Preparation of an Immunostimulant, the Disaccharide-Diepetide, N-Acetyl-.beta.-D-glucosaminyl-(1->4)-N-acetylmuramyl-L-alanyl-D-isoglutam ine, From a Bacterial Peptidoglycan," European J. Biochemistry, 143(2), 359-362 (Sep. 3, 1984).
Kanie et al., "Orthogonal Glycosylation Strategy in Oligosaccharide Synthesis," J. American Chemical Society, 116(26), 12073-12074 (Dec. 28, 1994).
Kantouci et al., "A Convenient Synthetic Route to the Disaccharide Repeating-Unit of Peptidoglycan," Carbohydrate Research, 162(2), 227-235 (May 1, 1987).
Kawata et al., "Preparation of Disaccharide Peptides with Immunostimulation From Microbial Cell Walls," Agricultural & Biological Chemistry, 48(7), 1783-1793 (Jul. 1984).
Keglevic et al.(I), "Isolation Procedure and Properties of Monomer Unit From Lysozyme Digest of Peptidoglycan Complex Excreted Into the Medium by Penicillin-Treated Brevibacterium Divaricatum Mutant," Biochemica et Biophysica Acta, 585(2), 273-281 (Jun. 12, 1979).
Keglevic et al.(II), "Aminolysis of N-Acetylmuramic Acid Lactones by Amino Acid and Peptide Esters--A Synthetic Route of the N-Acetylmuramosylamide Derivatives," Croatica Chemica Acta, 58(4), 569-581 (Mar. 6, 1986).
Kiso et al., "Synthesis and Immunoadjuvant Activities of the Repeating, Disaccharide-Dipeptide Unit of the Bacterial, Cell-Wall Peptidoglycan and of Some Carbohydrate Analogs," Carbohydrate Research, 104(2), 253-269 (Jun. 16, 1982).
Kusumoto et al. (I), "Chemical Synthesis and Biological Activities of Two Disaccharide Dipeptides Corresponding to the Repeating Units of Bacterial Peptidoglycan," Bulletin of the Chemical Society of Japan, 59, 1411-1417 (May 1986).
Kusumoto et al. (II), Synthesis of .beta.(1->4)-Linked Disaccharides of N-Acetylglycosamine and N-Acetyl Muramic Acid by Their Direct Condensation," Bulletin of the Chemical Society of Japan, 59, 1419-1423 (May 1986).
Kusumoto et al. (III), "Synthesis of N-Acetyl-.beta.-D-glucosaminyl-(1-4)-N-acetylmuramyl-L-alanyl-D-isoglutami ne," Tetrahedron Letters, (Issue No. 45), 4407-4410 (Nov. 1978).
Ledvina et al. (I), "Synthesis of O-[2-acetamido-2-deoxy-6-O-stearoyl- and -6-O-(2-tetradecylhexadecanoyl)-.beta.-D-glucopyranosyl]-(1->4)-N-acetylno rmuramoyl-L-.alpha.-aminobutanoyl-D-isoglutamine, Lipophilic Disaccharide Analogues of MDP," Carbohydrate Research, 251, 269-284 (Jan. 3, 1994).
Ledvina et al., (II), "An Alternative Synthesis of O-(2-acetamido-2-deoxy-.beta.-D-glucopyranosyl)-(1->4)-N-acetylnormuramoyl -L.alpha.-aminobutanoyl-D-isoglutamine," Coll. Czech Chem. Communications, 54(10), 2784-2794 (Oct. 1989).
Merser et al., "Synthesis of the Repeating Disaccharide Unit of the Glycan Moiety of the Bacterial Cell Wall Peptidoglycan," Tetrahedron Letters, (Issue No. 13), 1029-1032 (Mar. 1973).
Mukaiyama et al., "An Efficient Method for the Glucosylation of Hydroxy Compounds Using Glycopyranosyl Fluoride," Chemistry Letters, (Issue No. 3), 431-432 (Mar. 1981).
Nicolaou et al. (I), "A Mild and General Method for the Synthesis of O-Glycosides," J. American Chemical Society, 105(8), 2430-2434 (Apr. 20, 1983).
Nicolaou et al. (II), "Practical Synthesis of Oligosaccharides. Partial Synthesis of Avermectin B.sub.1a." J. American Chemical Society, 106(15), 4189-4192 (Jul. 25, 1984).
Nicolaou et al. (III), "Stereospecific Synthesis of Rhynchosporosides: A Family of Rungal Metaboliktes Causing Scald Disease in Barley and Other Grasses," J. American Chemical Society, 107(19), 5556-5558 (Sep. 18, 1985).
Nicolaou et al. (IV), "Total Synthesis of the Tumor-Associated Le.sup.X Family of Glycosphingolipids," J. American Chemical Society, 112(9), 3693-3695 (Apr. 25, 1990).
Pozsgay et al. (I), "Synthesis of a Di-, Tri-, and Tetrra-Saccharide Unit of the Group B Streptococcal Common Antigen," Carbohydrate Research, 179, 61-75 (Aug. 15, 1988).
Pozsgay et al. (II), "A New Method for the Synthesis of O-Glycosides from S-Glycosides," J. Organic Chemistry, 52(20), 4635-4637 Oct. 2, 1987).
Pozsgay et al. (III), "A New, Stereoselective Synthesis of Methyl 1,2-trans-1-thioglycosides," Tetrahedron Letters, 28(13), 1375-1378 (1987).
Sava et al., "Immunotherapy of Lewis Lung Carcinoma with Hydrosolube Peptidoglycan Monomer (PGM)." Cancer Immunology Immunotherapy, 15(2), 84-86 (Jul. 1983).
Termin et al. (I), "Synthesis of the GlcNAc.beta.(1->4)MurNAc.beta.(1->4)GlcNAc.beta. (1->4)MurNAc Tetrasaccharide of Bacterial Peptidoglycan," Liebigs Annalen der Chemie, 1992(5), 527-533 (May 1992).
Termin et al. (I), "6-O-Benzylierte Muraminsaure als Glycosylakzeptor--Synthese des GlcNAc-.beta.(1>4)-MurNAc-Disaccharids," Liebigs Annalen der Chemie, 1989(8), 789-795 (Aug. 1989).
Vosika et a., "Phase I Trial of ImmTher, a New Liposome-Incorporated Lipophilic Disaccharide Tripeptide," Journal of Immunotherapy, 10(4), 256-266 (Aug. 1991).

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