Abstract
Amino acids and peptides have been attached to the C-6 hydroxyls of the galactose and the N-acetylgalactosamine by first oxidizing the C-6 hydroxyls to the aldehydes by galactose oxidase in the presence of small amounts of catalase, followed by reductive amination (α-amino group) in the presence of cyanoborohydride. The activity of oxidized antifreeze glycoprotein was >70% of the original, and considerable activity has been retained with some substitutions on reductive amination using cyanoborohydride. The following were some activities retained (as compared with the oxidized antifreeze glycoprotein): Gly, 64; (Gly)2, 88; (Gly)3, 82; (Gly)4, 70; Gly-Gly-NH2, 44, Gly-Glu, 13; Gly-Leu, 40; Gly-Tyr, 57; Gly-Gly-Leu, 50; Gly-Gly-Phe, 30; and Gly-Gly-Val, 35. On amino acid analysis of acid hydrolysates, some release of the amino acid attached by amination occurred; e.g., Gly-Tyr gave 0.26 Gly and 0.49 Tyr per disaccharide.
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Ahmed, A. I., Osuga, D. T., and Feeney, R. E. (1973).J. Biol. Chem. 248, 8524–8527.
Brown, R. A., Yeh, Y., Burcham, T. S., and Feeney, R. E. (1985).Biopolymers 24, 1265–1270.
Burcham, T. S., Osuga, D. T., Rao, B. N. N., Bush, C. A., and Feeney, R. E. (1986a).J. Biol. Chem. 261, 6384–6389.
Burcham, T. S., Osuga, D. T., Yeh, Y., and Feeney, R. E. (1986b).J. Biol. Chem. 261, 6390–6397.
Bush, C. A., and Feeney, R. E. (1986).Int. J. Peptide Protein Res. 28, 386–397.
Bush, C. A., Feeney, R. E., Osuga, D. T., Ralapati, S., and Yeh, Y. (1981).Int. J. Peptide Protein Res. 17, 125–129.
DeVries, A. L., Komatsu, S. K., and Feeney, R. E. (1970)J. Biol. Chem. 245, 2901–2908.
Feeney, R. E. (1987).Int. J. Peptide Protein Res. 29, 145–161.
Feeney, R. E. (1988)Comments Agric. Food Chem. 1, 147–181.
Feeney, R. E., and Yeh, Y. (1978).Adv. Protein Chem. 32, 191–282.
Feeney, R. E., Osuga, D. T., Ward, F. C., Rearick, J. I., Glasgow, L. R., Sadler, J. E., and Hill, R. L. (1978). Abstr. Div. Biol. Chem., Am. Chem. Soc. Meeting, Miami Beach, Sept. 10–15.
Feeney, R. E., Burcham, T. S., and Yeh, Y. (1986).Annu. Rev. Biophys. Biophys. Chem. 15, 59–78.
Franks, F., and Morris, E. R. (1978).Biochim. Biophys. Acta 540, 346–356.
Harrison, K., Hallett, J., Burcham, T. S., Feeney, R. E., Kerr, W. L., and Yeh, Y. (1987).Nature (Lond.)328, 241–243.
Kerr, W. L., Feeney, R. E., Osuga, D. T., and Reid, D. S. (1985).Cryo-Letters 6, 371–378.
Komatsu, S. K., DeVries, A. L., and Feeney, R. E. (1970).J. Biol. Chem. 245, 2909–2913.
Kozulic, B., Leustek, I., Pavlovic, B., Mildner, P., and Barbaric, S. (1987).Appl. Biochem. Biotechnol 15, 265–278.
Luna, L. G., ed. (1968).Manual of Histologic Staining Methods of the Armed Forces Institute of Pathology, 3rd ed., McGraw-Hill, New York.
Matta, K. L., Johnson, E. A., and Barlow, J. J. (1973).Carbohydr. Res. 26, 215–218.
Mulvihill, D. M., Geoghegan, K. F., Yeh, Y., Deremer, K., Osuga, D. T., Ward, F. C., and Feeney, R. E. (1980).J. Biol. Chem. 255, 659–662.
Osuga, D. T., and Feeney, R. E. (1978).J. Biol. Chem. 253, 5338–5343.
Osuga, D. T., Ward, F. C., Yeh, Y., and Feeney, R. E. (1978).J. Biol. Chem. 253, 6669–6672.
Powning, R. F., and Irzykiewicz, H. (1967).J. Chromatogr. 29, 115–119.
Raymond, J. A., and DeVries, A. L. (1972).Cryobiology 9, 541–547.
Stacey, M. (1944).J. Chem. Soc. 1944, 272–274.
Stahl, E., ed. (1969).Thin Layer Chromatography, Springer-Verlag, New York.
Stoffyn, A., and Stoffyn, P. (1966).J. Org. Chem. 32, 4001–4006.
Vandenheede, J., Ahmed, A. I., and Feeney, R. E. (1972).J. Biol. Chem. 247, 7885–7889.
Yamasaki, R. B., Shimer, D. A., and Feeney, R. E. (1981).Anal. Biochem. 111, 220–226.
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Osuga, D.T., Feather, M.S., Shah, M.J. et al. Modification of galactose andN-acetylgalactosamine residues by oxidation of C-6 hydroxyls to the aldehydes followed by reductive amination: Model systems and antifreeze glycoproteins. J Protein Chem 8, 519–528 (1989). https://doi.org/10.1007/BF01026436
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DOI: https://doi.org/10.1007/BF01026436