Method of forming multiple glycosidic linkages in a single step

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

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

530395, 536 111, 536 41, 536 64, 536 186, 536124, 536126, A61K 3816, C07K 100, C07H 100, C07H 1524

Patent

active

056356129

ABSTRACT:
The invention relates to methods that permit the rapid construction of oligosaccharides and other glycoconjugates. Methods for forming multiple glycosidic linkages in solution in a single step are disclosed. The invention takes advantage of the discovery that the relative reactivity of glycoside residues containing anomeric sulfoxides and nucleophilic functional groups can be controlled. In another aspect of the invention, the reactivity of activated anomeric sugar sulfoxides is utilized in a solid phase method for the formation of glycosidic linkages. The methods disclosed may be applied to the preparation of specific oligosaccharides and other glycoconjugates, as well as to the preparation of glycosidic libraries comprising mixtures of various oligosaccharides, including glycoconjugates, which can be screened for biological activity.

REFERENCES:
patent: 3036061 (1962-05-01), MacPhillamy et al.
patent: 3896238 (1975-07-01), Smith
patent: 3952099 (1976-04-01), Smith
patent: 4046886 (1977-09-01), Smith
patent: 4130643 (1978-12-01), Smith
patent: 4130667 (1978-12-01), Smith
patent: 4148887 (1979-04-01), Smith
patent: 4148893 (1979-04-01), Smith
patent: 4148917 (1979-04-01), Smith
patent: 4148924 (1979-04-01), Smith et al.
patent: 4150114 (1979-04-01), Smith
patent: 4360663 (1982-11-01), Asano et al.
patent: 4548922 (1985-10-01), Carey et al.
patent: 4746508 (1988-05-01), Carey et al.
patent: 4865848 (1989-09-01), Cheng et al.
patent: 4900555 (1990-02-01), Cheng et al.
patent: 4902505 (1990-02-01), Pardridge et al.
patent: 4959358 (1990-09-01), Carey et al.
patent: 5116817 (1992-05-01), Anik
patent: 5144017 (1992-09-01), LaBella et al.
patent: 5338837 (1994-08-01), Kahne
Tetrahedron Letters, (1987), vol. 28, No. 40, pp. 4701-4704, "Sulfenate Esters as Glycosyl Acceptors: A Novel Approach to O-Glycosides from Thioglycosides and Sulfenate Esters", Ito et al.
Tetrahedron Letters, (1987), vol. 28, No. 24, pp. 2723-2726, "Sulfenate Esters as Glycosyl Acceptors: A Novel Approach to the Synthesis of 2-Deoxyglycosides", Ito et al.
J. Am. Chem. Soc., (1983), vol. 105, No. 8, pp. 2430-2433, "A Mild and General Method for the Synthesis of O-Glycosides", Nicolaou et al.
Carbohydrate Research, (1983), vol. 116, pp. 162-165, "A Reinvestigation of Glycosidation Reactions Using 1-Thioglycosides as Glycosyl Donors and Thiophillic Cations as Promoters", Garegg et al.
Carbohydrate Research, (1985), vol. 139, pp. 105-113, "Synthesis of a tri-and a Hepta-Saccharide which Contain .alpha.-L-Fucopyanosyl Groups and are Part of the Complex Type of Carbohydrate Moiety of Glycoproteins", Lonn.
pp. 3919-3922, "Synthesis of 1.2-CIS-Linked Glycosides using Dimethl(Methylthio)Sulfonium Triflate as Promoter and Thioglycosides and Glycosyl Donors", Andersson et al.
Pp. 1061-1064, "Benzeneselenenyl Triflate as a Promoter of Thioglycosides: A New Method for O-Glycosylation Using Thioglycosides", Ito et al.
Biochemistry, (1989), vol. 86, pp. 6553-6556, "Cholesteryl-Conjugated Oligonucleotides: Synthesis, Properties, and Activity as Inhibitors of Replication of Human Immunodeficiency Virus in Cell Culture", Letsinger et al.
J. Am. Chem. Soc., (1989), vol. 111, No. 17, pp. 6881-6882, "Glycosylation of Unreactive Substrates", Kahne et al.
Tetrahedron Letters, (1988) vol. 29, No. 38, pp. 4873-4876, "Preparation of Cyclic Ether Acetals from2-benzenesulphonyl Derivatives: A New Mild Glycosidation Procedure", Brown et al.
Carbohydrate Research, (1988), vol. 177, pp. c13-c17, "Alkyl Sulfenyl Triflate as Activator in the Thioglycoside-mediated Formation of .beta.-Glycosidic Linkages during Oligosaccharide Syntheses", Dasgupta et al.
(1973), vol. 27, pp. 55-61, "A Potentially Versatile Synthesis of Glycosides", Ferrier et al.
Chemical Abstracts, (1991), vol. 115, No. 7.
Proc. Natl. Acad. Sci., (1985), vol. 82, pp. 7419-7423, "Nasal Absorption of Insulin: Enhancement by Hydrophobic Bile Salts", Gordon et al.
Proc. Natl. Acad. Sci., (1981), vol. 78, pp. 5908-5912, "Properties of the Gastric Proton Pump in Unstimulated Permeable Gastric Glands", Malinowska et al.
Neurosurgery, (1983), vol. 12, No. 6, pp. 606-612, "Intracarotoid Dehydrocholate Infusion: A New Method for Prolonged Reversible Blood-Brain Barrier Disruption", Spigelman et al.
Chemical Abstracts, 94:98644b, "Interactions Between Deoxycholic Acid Glucuronides and Glucuronidase,", Oehlke.
Chemical Abstracts, 115:72019d, "Bile Acid Derivatives, A Process for Their Production and Their Use As Medicines.", Kramer et al.
Chemical Abstracts, 92:59167n, "CMT-Selectin Syntheses. Preparation of Deoxycholic Acid Glucuronides.", Oehlke.
Pharmazie, (1979), vol. 34, H.7, pp. 383-386, "Darstllung Von Desoxycholsaureglucuroniden", Oehlke.
J. Org. Chem., (1986), vol. 51, No. 4, pp. 533-536, "Two New Steroidal Glycoside Sulfates, Longicaudoside-A and -B, from the Mediterranean Ophiuroid Ophioderma Longicaudum", Riccio et al. Exhibit A, pp. 1-8, Claims 1-5, 7-8, 14, 19, 51-53, 56-75, and 77-82.
Ito et al Tetrahedron Ltts vol. 28 No. 24 pp. 2723-2726 (1987).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Method of forming multiple glycosidic linkages in a single step does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method of forming multiple glycosidic linkages in a single step, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of forming multiple glycosidic linkages in a single step will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-392589

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.