Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing compound containing saccharide radical
Patent
1986-03-07
1990-05-15
Wax, Robert
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing compound containing saccharide radical
435 681, 435 99, 435193, 435201, 530395, C12P 1918
Patent
active
049257960
ABSTRACT:
A method for modifying eukaryotic and prokaryotic proteins to extend their in vivo circulatory lifetimes. In the preferred embodiment, enzymatic and/or chemical treatments are used to produce a modified protein carrying one or more covalently attached trisaccharide, sialic acid.fwdarw.galactose.fwdarw.N-acetylglucosamine.fwdarw.(SA.fwdarw.Gal.fwd arw.GlcNac.fwdarw.), or tetrasaccharide (SA.fwdarw.Gal.fwdarw.GlcNAc.fwdarw.GlcNAc.fwdarw.) moieties. The method can be applied to any natural or recombinant protein possessing asparagine-linked oligosaccharides or to any non-glycosylated protein that can be chemically or enzymatically derivatized with the appropriate carbohydrate units. Following injection into an animal, the modified glycoproteins are protected from premature clearance by cells of the liver and reticulo-endothelial system which recognize and rapidly internalize circulating glycoproteins with carbohydrate chains containing terminal Gal, GlnNAc, fucose or mannose residues. The method can also be used to mask antigenic determinants on foreign proteins which would otherwise produce an immune response or to "target" a protein for recognition by sugar-specific cell surface receptors.
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Berger, Eric G., Urs F. Greber and Klaus Mosbach, "Galactosyltransferase-dependent Sialylation of complex and endo-N-acetylglucosaminidase H-treated core N-glycans", FEBS Letters, vol. 203, No. 1, Jul. 1986, pp. 64-68.
"Requirements of Cleavage of High Mannose Oligosaccharides in Glycoproteins by Peptide N-Glycosidase F" by F. K. Chu in J. Biol. Chem., 261, 172-177, (Jan. 5, 1986).
"Optimizing Hydrolysis of N-Linked High Mannose Oligosaccharides by Endo-.beta.N-acetylglucosaminidase H" by R. B. Trimble and R. Maley in Anal. Biochem., 141, 515-522, (1984).
"Binding of Synthetic Oligosacchrides to the Hepatic Gal/GlcNAc Lectin" by Y. C. Lee et al in J. Biol. Chem., 258, 199-202, (1983).
"Preparation of Neoglycoproteins Using 2-Imino-Methoxyethyl-1-Thiolycosides" by C. P. Stowell and Y. C. Lee, Meth. Enzymol., 83, 278-288, (1982).
"Neoglycoproteins: In Vitro, Introduction of Glycosyl Units at Glutamines in .beta.-Casein Using Transglutaminase" by S. B. Yan and F. Wold, Biochemistry, 23, 3759-3765, (1984).
"Effect of Glycosylation in the In Vivo Circulating Half-Life Ribonuclease" by J. W. Baynes and F. Wold, J. Biol. Chem., 251, 6016-6024, (1976).
"Sialkylation of Glycoprotein Oligosaccharides N-Linked to Asparagine" by J. Weinstein, U. de Souza-e-Silva and J. C. Paulson, in J. Biol. Chem., 257, 13845-13853, (1982).
"Sialylation of Glycoprotein Oligosaccharides with N-Acetyl-, N-Glycolyl- and N,O-Diacetylneuraminic Acids" by H. H. Higa and J. C. Paulson, J. Biol. Chem., 260, 8838-8847, (1985).
"Physical and Chemical Studies of Ceruloplasmin, VIII, Preparation of N-Acetylneuraminic Acid-1-.sup.14 C-Labeled Ceruloplasmin" by J. Hickman et al, J. Biol. Chem., 245, 759-766, (1970).
"N-Asparagine-Linked Oligosaccharides: Processing" by I. Tabas et al in Methods in Enzymology, 83, 416-429, (Academic Press, 1982).
"Structure, Biosynthesis and Functions of Glycoprotein Glycans" by E. G. Berger et al in Experientia, 38 (10), 1129-1258, (1982).
Bergh Michel L. E.
Hubbard S. Catherine
Rasmussen James R.
Massachusetts Institute of Technology
Wax Robert
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