By R. W. Ledeen, R. K. Yu (auth.), Abraham Rosenberg, Cara-Lynne Schengrund (eds.)
There is a startling volume of analysis task about the position of sialic acid in mammalian cells and within the mammalian organism. One could figure within the early literature premonitions of compounds containing sialic acid, traceable via descriptions of colour reactions, way back to the flip of the century. paintings spanning the Nineteen Thirties to the Nineteen Fifties culmi nated within the crystallization of sialic acid from a wide selection of organic fabrics. the ever-present nature of the sialic acids, and the organic significance of the elements within which they take place, then grew to become ordinarily occur. considering the fact that then, the chemistry and metabolism of sialic acid and its incidence, significantly, yet now not solely, within the outer cellphone surfaces of mammalian cells and in key extracellular glycoproteins, have acquired nice recognition. The involvement of sialic acid-containing elements in tumorigenicity and in different metabolic and infectious pathological stipulations, and within the progress, improvement, and integrity of mammalian cells has completed common acceptance. extensive inquiry into the organic roles of sialic acid maintains in plenty of examine laboratories in the course of the international. This ebook is meant to symbolize for the uninitiated in addition to for the specialist a large and distinct evaluate of the present country of data. significant efforts and pioneering holiday throughs have emerged from numerous laboratories, positioned on each side of the Atlantic, of which we make no targeted person point out right here due to the fact they're going to to a point look within the pages that follow.
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W. Ledeen and R. K. ~ H-(-OAc I H-(-OAc I (H20Ac I Ph 3 == P-(-O(2 HS 00 XLVII y XLVIII I H-(-OH I AcNH-(-H I HO-(-H I H-(-OH I H-(-OH I (H20H HO-(-(OOH I (H2 I H-(-OH (HO I H-(-OAc I AcNH-(-H I AcO-(-H I H-(-OAc I H-(-OAc I (H 2 0Ac XLVI I AcNH-(-H I O-(-H I H-(-OH I H-(-OH I (H20H IX FIGURE 13. Sialic acid synthesis by the procedure of Mirzayanova et al. (1970). , 1957), resorcinol (Svennerholm, 1957b), dimethylaminobenzaldehyde (Werner and Odin, 1952), and thiobarbituric acid (Warren, 1959; Aminoff, 1959), but only a few of these are still in use.
Although the various anomeric pairs could be differentiated by physical and enzymatic means, the precise structures remained uncertain until it was established that these reactions followed III HO, /H XXVIII OR /C:CC~n--r COOR HOCH2~ AcNH OH XXIX FIGURE 9. HO~~(COOH HOCH2 H,C-- OH AcNH 0 OR OH XXX General procedures for synthesis of l3-ketosides (XXIX) and a-ketosides (XXX) of sialic acids. Ketoside group Methyl Methyl Methyl Methyl n-Amyl n-Amyl n-Hexyl n-Hexyl Carboxymethyl Benzyl H Acetyl Acetyla Acetyla Acetyl Acetyl Acetyl Acetyl Acetyl Acetyl 199-200 175-177 193-195 Acetyl 97-98 115-130 111-115 137-138 124-125 199-200 Melting or decomposition point,OC Acetyl Acetyl 4,7,8,9-0Substitution -24(H2O) -44 -39(CH3 OH) -46(CH3 OH) -45(H2O) -11(CH3 OH) -23(H2O) -42(DMSO)b -27(AcOH) -12(AcOH) -20(H2 0) -55(H20) [alD (solvent) B6hm and Baumeister (1955) Gielen (1965; 1967a) Klenk and Lauenstein (1952) Kuhn et al.
NANA with two acetyl substituents at C7-CS or C 7-C9 failed to react due to absence of vicinal hydroxyls (Blix and Lindberg, 1960). Mild periodate oxidation of sialoglycoproteins was shown to result 36 R. W. Ledeen and R. K. Yu in selective modification of the sialic acid moieties with no apparent change in other carbohydrates or amino acids (van Lenten and Ashwell, 1971; Suttajit and Winzler, 1971). Subsequent reduction with sodium borohydride produced analogs having one or two carbons less than the original sialic acid; such derivatives could be conveniently labeled by carrying out the reduction with tritiated borohydride.