Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Reexamination Certificate
2007-05-01
2007-05-01
Jiang, Shaojia Anna (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C536S005000, C536S001110, C536S004100, C536S109000, C536S018600, C536S018700, C536S123100, C536S123130, C536S117000, C536S017900, C536S018500, C536S126000, C549S222000, C435S097000
Reexamination Certificate
active
10033175
ABSTRACT:
One aspect of the present invention relates to differentially protected glycosyl phosphates. Another aspect of the present invention relates to the preparation of glycosyl phosphates from glycal precursors. In another aspect of the present invention, glycosyl phosphates are used as glycosyl donors in glycosylation reactions.
REFERENCES:
patent: 4785084 (1988-11-01), Warren et al.
patent: 5095123 (1992-03-01), Sabesan
patent: 5369017 (1994-11-01), Wong et al.
patent: 5374655 (1994-12-01), Kashem et al.
patent: 5516665 (1996-05-01), Wong
patent: 5716812 (1998-02-01), Withers et al.
patent: 5721338 (1998-02-01), Imperiali et al.
patent: 5728554 (1998-03-01), Bayer et al.
patent: 5759823 (1998-06-01), Wong et al.
patent: 5811539 (1998-09-01), Seiffert-Stoeriko et al.
patent: 5922577 (1999-07-01), Defrees et al.
patent: 5952203 (1999-09-01), Withers et al.
patent: 5952454 (1999-09-01), Kovac et al.
patent: 5994502 (1999-11-01), Imperiali et al.
patent: 6013779 (2000-01-01), Wong et al.
patent: 6022713 (2000-02-01), Noguchi et al.
patent: 6030815 (2000-02-01), Defrees et al.
patent: 6077695 (2000-06-01), Nilsson
patent: 6323339 (2001-11-01), Seeberger et al.
patent: 6693178 (2004-02-01), Buchwald et al.
patent: WO 96/24683 (1996-08-01), None
patent: WO 96/32491 (1996-10-01), None
patent: WO 98/46784 (1998-10-01), None
patent: WO 99/ 28491 (1999-06-01), None
patent: WO 99/47694 (1999-09-01), None
patent: WO 99/47695 (1999-09-01), None
patent: WO 00/20428 (2000-04-01), None
Hashimoto et al. “A rapid and efficient synthesis of 1,2-trans-B-linked glycosides via benzyl- or benzoyl-protected glycopyranos phosphates.” J. Chem. Soc. Chem. Commun. pp. 685-687, 1989.
Stevens et al. Carbohydrate Res., 11:93-98, 1969.
Danilov et al. Zhurnal Obshchei Khimii, vol. 45, 10, 2307-2311, 1975.
Schmid et al. “Activation of glycosyl phosphates by in situ conversion to glycosyl iodides under neutral conditions in concentrated solutions of lithium perchlorate in organic solvents.” Tetrahedron Letters, vol. 37, No. 22, pp. 3837-3840, 1996.
Merck Index, Twelfth Edition, 1996, pp. 759, compound 4470.
Hashimoto et al.; “Oligosaccharide Synthesis Based on Glycosyl Donors and Acceptors Carrying Phosphorus Containing Carving Groups”, Tetrahedron Letters 38 (29): 5181-5184 (1997).
Morales et al.; “Carbohydrate- Carbohydrate Interactions in Water with Glycophanes as Model Systems”, J. Org. Chem. 63. 9212-9222 (1998).
Torgov et al. “Synthesis of Oligosaccharide Fragments of the Repeating UnitSalmonellaKentucky O-specific Polysaccharide and Conversion of the Oligosaccharides Into the Glycosyl Phosphates”, Carbohydrate Research 161 : 97-112 (1987).
Plante and Seeberger ; “ Anomeric Phosphorodithioates as Novel Glycosylating Agents”, J. Org. Chem. 63 : 9150-9151 (1998).
Seeberger et al., “Synthesis of Biologically Important Oligosaccharides and Other Glycoconjugates by the Glycal Assembly Method”, Aldrichimica Acta 30 (3): 75-92 (1997).
Zheng et al., “ Solid Support Oligosaccharide Synthesis : Construction of β-Linked Oligosaccharides by Coupling of Glycal Derived Thioethyl Glycosyl Donors”, J. Org. Chem. 63:1126-1130 (1998).
Chen, et al. Glycosyl Phosphoramidinidates As Versatile Glycosyl Donors, Heterocycles, 45(7): 124 (1997).
Hashimoto, et al.; ““Armed Diarmed”Glycosidation Strategy Based on Glycosyl Donors and Acceptors Carrying Phosphoroamidate as a Leaving Group: A Convergent Synthesis of Globotriaosylceramide”, Tetrahedron Letters 38 (52): 8969-8972 (1997).
Hashimoto, et al.; “A Rapid and Efficient Synthesis of 1,3- trans-β-Linked Glycosides via Benzyl- or Benzoyl-Protected Glycopyranosyl Phosphates”, J. Chem. Soc. Chem. Commun. pp. 685-687 (1989).
Laupichler , et al.; “Convenient Iodonium-Promoted Stereoselective Synthesis of 2-Deoxy-α-glycosides by Use of S-(2-Deoxyglycosyl) Phosphorodithioates as Donors”, Synthesis , pp. 1133-1136 (Nov. 1992).
Liang, et al.; “Parallele Synthesis and Screening of a Solid Phase Carbohydrate Library”, Science, 274 : 1520-1522 (Nov. 29, 1996).
Paulsen et al.; “Synthese Von DD-Heptosephosphaten als Substrate oder Potentielle Inhibitoren für die Heptose-Synthetase”, Liebigs Ann. Chem. pp. 389-397 (1994).
Plante and Seeberger; “Anomeric Phosphorodithioates as Novel Glycosylating Agents”, J. Org. Chem. 63 : 9150-9151 (1998).
Timmers, et al. “An Expeditious Route to Streptococci and Enterococci Glycolipids VLA Ring-Opening of 1.2—Anhydrosugars”, J. Carbohydrate Chemistry 17 (3): 471-487 (1998).
Watanabe, et al.; “Dibenzyl Phosphorofluoridate, A New Phosphorylating Agent”, Tetrahedron Letters 29 (45) pp. 5763-5764 (1988).
Danilov, L. L. et al., “Stereospecific Synthesis of 1,2-trans-Glycosyl Phosphates”,Zhumal Obshchel Khimβ,46(10):2907-2911 (Oct. 1975).
Grujić-Injac, B., et al., “The Structure of a New Phospholipid from the Koilin-Glandular Layer of Chicken Gizzard”,Hoope-Seylera Z. Physiol. Chem.,S68;499-604 (Apr. 1977).
Schmidt, R, R. et al, “Glycosylphosphate aus Glycosyl(trichloracetlmidaten)”,Liebigs Ann. Chem.,10:680-691 (1984).
European Search Report dated Apr. 22, 2005.
Stevens, C. L. et al., “Proof of Structure and Synthesis of α-D-Glucopyranosyl (Dihydrogen Phosphate)”,Carbohyd. Res.,11:93-98 (1969).
Volkova, L. V. et al., “A novel, stereospecific synthesis of β-D-glucopyranosyl phosphate”,Carbohyd. Res.,32:165-166 (1974).
Plante Obadiah J.
Seeberger Peter H.
Foley & Hoag LLP
Gordon Dana M.
Jiang Shaojia Anna
Khare Devesh
Massachusetts Institute of Technology
LandOfFree
Synthesis of oligosaccharides, reagents and methods related... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Synthesis of oligosaccharides, reagents and methods related..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of oligosaccharides, reagents and methods related... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3802402