Preparation and nutritional properties of caseins covalently modified with sugars. Reductive alkylation of lysines with glucose, fructose, or lactose

Abstract

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Contribution of Protein Flexibility to the Foaming Properties of Casein

“…Reductive alkylation of lysyl residues with sugar was carried out as described by Lee et al (1979). Different times of reaction resulted in different levels of modification.…”

Chemical modifications of proteins: history and applications

“…Reagents and procedures have been developed to decrease immunogenicity (9, 20), to increase and decrease susceptibility to proteolysis (22-23), to increase UV or visible absorbancy (14), to introduce fluorescent labels (25,16), spin labels (27), radiolabels , various metal ions (22), magnetic microspheres (22,23), and electron-dense substituents (24), to increase the content of certain low-abundance nonradioactive isotopes (25) …”

“…Reagents and procedures have been developed to decrease immunogenicity (9,20), to increase and decrease susceptibility to proteolysis (22)(23), to increase UV or visible absorbancy (14), to introduce fluorescent labels (25,16), spin labels (27), radiolabels , various metal ions (22), magnetic microspheres (22,23), and electron-dense substituents (24), to increase the content of certain low-abundance nonradioactive isotopes (25), and to attach several different types of carbohydrate moieties (26)(27)(28)(29), biotin (30), and a number of other biospecific recognition groups (i.e., avidin, streptavidin, antibodies, protein A, protein G, lectins, and others (32)). Procedures also have been developed to effect the cleavage of peptide chains (32,33); to modify enzyme specificity (34); to modify the terminal hydroxyls of galactosyl residues in glycoproteins (35); to introduce intramo- 1 The Ohio State University.…”

Chemical and Enzymatic Protein Modifications and Functionality Enhancement

“…Different from enzymatic glycosylation, which attaches mono-saccharides or oligosaccharides to the alcoholic hydroxyl group of serine and threonine residues or to the amide group of asparagine residue, chemical glycosylation of a food protein (Kato, Watanabe, and Sato 1981;Kato et al 1995;Aoki et al 1997;Wahyuni, Ishizaki, and Tanaka 1999;Saeki 1999;Katayama, Shima, and Saeki 2002;Kato 2002;Paraman, Hettiarachchy, and Schaefer 2007;Jiménez-Castaño, Villamiel, and López-Fandiño 2007;Nakamura et al 2008) or via reductive alkylation ( Figure 7.6) (Schwartz and Gray 1977;Lee et al 1979;Courthaudon, Colas, and Lorient 1989;Baniel et al 1992). Not only monosaccharides (Lee et al 1979;Kato, Watanabe, and Sato 1981;Saeki 1999;Katayama, Shima, and Saeki 2002;Paraman, Hettiarachchy, and Schaefer 2007) and disaccharides (Courthaudon, Colas, and Lorient 1989;Baniel et al 1992), but also polysaccharides, such as chitosan, galactomannan, pectin, arabinogalactan, xyloglucan, dextran, dextrin, cyclodextrin, xanthan gum (Saeki 1999;Kato 2002;Jiménez-Castaño, Villamiel, and López-Fandiño 2007;Paraman, Hettiarachchy, and Schaefer 2007;Nakamura et al 2008), and even glucose 6-phosphate (Kato et al 1995;Aoki et al 1997;Wahyuni, Ishizaki, and Tanaka 1999), can be attached to a protein via the Maillard reaction.…”

“…Not only monosaccharides (Lee et al 1979;Kato, Watanabe, and Sato 1981;Saeki 1999;Katayama, Shima, and Saeki 2002;Paraman, Hettiarachchy, and Schaefer 2007) and disaccharides (Courthaudon, Colas, and Lorient 1989;Baniel et al 1992), but also polysaccharides, such as chitosan, galactomannan, pectin, arabinogalactan, xyloglucan, dextran, dextrin, cyclodextrin, xanthan gum (Saeki 1999;Kato 2002;Jiménez-Castaño, Villamiel, and López-Fandiño 2007;Paraman, Hettiarachchy, and Schaefer 2007;Nakamura et al 2008), and even glucose 6-phosphate (Kato et al 1995;Aoki et al 1997;Wahyuni, Ishizaki, and Tanaka 1999), can be attached to a protein via the Maillard reaction. During the reaction, the aldehyde group of an aldose or a polysaccharide first attaches to the amino group of a protein to form aldimine (Schiff base).…”