Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1994-01-10
1997-04-01
Hollinden, Gary E.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
5361231, 53612313, 536124, 536120, C07G 300, C07H 100, C07H 1504, C08B 3700
Patent
active
056166982
ABSTRACT:
The present invention provides improved syntheses of oligosacchairdes. In accordance with preferred embodiments, anomeric specificity in such syntheses can be attained using polymer-supported liquid synthetic design with certain novel diether linkers. The present invention also provides novel strategies for capping imcompletely glycosylated hydroxyls.
REFERENCES:
patent: 3173892 (1965-03-01), Kun
patent: 3853708 (1974-12-01), Porath et al.
patent: 3941849 (1976-03-01), Herold
patent: 4029720 (1977-06-01), Seiler et al.
patent: 4083834 (1978-04-01), Komatsu et al.
patent: 4085168 (1978-04-01), Milkovich et al.
patent: 4609546 (1986-09-01), Hiratani
patent: 4908405 (1990-03-01), Bayer et al.
patent: 5180674 (1993-01-01), Roth
Bayer, E. Towards the Chemical Synthesis of Proteins Angew. Chem. Int. Ed. 1991 30:113-216.
Bayer et al. Liquid Phase Synthesis of Peptides Nature 1972 237:512.
Bonora et al. Large scale, liquid phase synthesis of oligonucleotides by the phosphoramidite approach Nucleic Acids Res 1993 21:1213-1217.
Bonora et al. HELP (High Efficiency Liquid Phase) new oligonucleotide synthesis on soluble polymeric support Nucleic Acids Res 1990 18:3155.
Danishefsky et al. A Strategy for the Solid-Phase Synthesis of Oligosacchardies Science 1993 260:1307.
Douglas et al. Polymer-Supported Solution Synthesis of Oligosaccharides Am. Chem. Soc. 1991 113:5095.
Frechet J. Synthesis and Application of Organic Polymers as Supports and Portecting Groups Tetrahedron 1981 37:663.
Frechet J. Polymer-supported Synthesis of Oligosaccharides Polymer-Supported Reactions in Organic Synthesis 1980 Ch 8, 407.
Frechet J. Synthesis Using Polymer-supported Protecting Groups Polymer-Supported Reactions in Organic Synthesis 1980 Ch 6, 293.
Frechet et al. Solid-Phase Synthesis of Oligosaccharides Carbohydr. Res. 1991 22:399.
Frechet et al. Solid-Phase Synthesis of Oligosaccharides J. Am. Chem. Soc. 1971, 93;492.
Friesen et al. On the Use of the Haloetherification Method to Synthesize Fully Functionalized Disaccharides Tetrahedron 1990 46:103-112.
Friesen et al. On the Controlled Oxidative Coupling of Glycals J. Am. Chem. Soc. 1989 111:6656-6660.
Fugedi et al. Thioglycosides as Glycosylating Agents in Oligosaccharide Synthesis Glycoconjugate J. 1987 4:97.
Ichikawa et al. Chemical-Enzymatic Synthesis and Conformational Analysis of Sialyl Lewis x and Derivatives J. Am. Chem. Soc. 1992 114:9283-9298.
Kamaike et al. Efficient Syntheses of An Oligonucleotide on A Cellulose Acetate Derivative As A Novel Polymer-Support Using Phosphotriester Approach Tetrahedron 1988 29:647-650.
Kanie et al. Glycosylation Using Methythioglycosides fo N-Acetylneuraminic Acid and Dimethyl Sulfonium triflate J. Carbohy. Chem. 1988 7:501.
Kaur et al. Use of N-Acetylglucosaminyltransferases I and II in the preparative synthesis of oligosaccharides Carbohy. Res. 1991 210:145-153.
Look et al. A Combined Chemical and Enzymatic Strategy for the Construction of Carbohydrate-Containing Antigen Core Units J. Org. Chem. 1993 58:4326.
Mathur et al. Oligosaccharide Synthesis on Polymer Supports Polymers as Aids in Organic Chemistry Academic Press New York, 1980 Ch 6, 105.
Mereyala et al. Stereoselective Synthesis of .alpha.-Linked Saccharides Tetrahedron 1991 47:6435-6448.
Mootoo et al. n-Pentenyl Glyosides Permit the Chemospecific Liberation of the Anomeric Center Am. Chem. Soc. 1988 110:2662-2663.
Mutter et al. The Liquid-Phase method for Peptide Synthesis The Peptides Academic Press: New York 1980 Ch. 2, 286.
Paulsen H. Syntheses, Conformations and X-Ray Structure Analyses of the Saccharide Chaims from the Core Regions of Glycoproteins Angew. Chem. Int. Ed. 1990 29:823.
Paulsen H. Advances in Selective Chemical Syntheses of Complex Oligosaccharides Angew. Chem. Int. Ed. 1982 21:155.
Schmidt R. New Methods for the Synthesis of Glycosides and Oligosaccharides Angew. Chem. Int. Ed. 1986 25:212.
Toshima et al. Recent Progress in O-Glycosylation Methods and Its Application to Natural Products Synthesis Chem Rev. 1983 93:1503-1531.
Wong et al. Enzymatic Synthesis of N-and O-Linked Glycopeptides J. Am. Chem. Soc. 1993 115:5893.
Wong et al. Probing the Acceptor Specificity of .beta.-1,4-Galactosyltransferase for the Development of Enzymatic Synthesis of Novel Oligosaccharides, J. Am. Chem. Soc., 1991, 113, pp. 8137-8145.
Veenerman et al. Synthesis of Carbohydrate-Antigenic Structures of Mycobacterium Tuberculosis Using and Iodonium Ion Promoted Gylcosidation Approach J. Carbohy. Chem. 1990 9:783-796.
Zehavi U. Applications of Photosensitive Protecting Groups in Carbohydrate Chemistry Advances in Carbohy. Chem. Biochem. 1988 46:179.
Douglas Stephen P.
Krepinsky Jiri J.
Whitfield Dennis M.
Hollinden Gary E.
University of Toronto - Innovations Foundation
White Everett
LandOfFree
Polymer-supported solution synthesis of oligosaccharides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Polymer-supported solution synthesis of oligosaccharides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Polymer-supported solution synthesis of oligosaccharides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-540016