By R. W. Ledeen, R. K. Yu (auth.), Abraham Rosenberg, Cara-Lynne Schengrund (eds.)
There is a startling volume of analysis task in regards to the position of sialic acid in mammalian cells and within the mammalian organism. One may possibly figure within the early literature premonitions of compounds containing sialic acid, traceable by means of descriptions of colour reactions, way back to the flip of the century. paintings spanning the Thirties to the Nineteen Fifties culmi nated within the crystallization of sialic acid from a large choice of organic fabrics. the ever-present nature of the sialic acids, and the organic significance of the elements within which they take place, then turned regularly appear. because then, the chemistry and metabolism of sialic acid and its incidence, particularly, yet no longer completely, within the outer mobilephone surfaces of mammalian cells and in key extracellular glycoproteins, have acquired nice realization. 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 accomplished common reputation. in depth inquiry into the organic roles of sialic acid keeps in lots of learn laboratories through the international. This booklet is meant to symbolize for the uninitiated in addition to for the specialist a large and precise assessment of the present nation of information. significant efforts and pioneering holiday throughs have emerged from a number of laboratories, positioned on each side of the Atlantic, of which we make no particular person point out right here when you consider that they're going to to a point seem within the pages that follow.
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Additional info for Biological Roles of Sialic Acid
Use of N-acetyl-o-mannosamine itself in the aldol condensation gave the same product in similar yield (Brug and Paerels, 1958), but the yield could be increased to 8-10% by prolonging the reaction period to 48 hr (Carroll and Cornforth, 1960). , 1969). , 1969). Chemistry and Analysis of Sialic Acid 37 o II Me3(0( - ( = (-OK I I (H (~ I'd (HO I AcNH-(-H I HO-(-H I H-(-O I ~ H-~-OH /(HPh (HO I AcNH-(-H I HO-(-H I H-(-OH I H-(-OH I (H2 0H ~H20/ 0( Me 3 I (=0 I (H 20 XXXIX 0 AcNH-(-H I HO-(-H I H-(-O I ~ H-(-OH (HPh + XLII (HK I (=0 I (=0 I o 0( Me 3 II Me3(0(-(=(-OK I I (~ ("0 XLI / 0 XL (t]_0 I / ,>eY AcNH-(-H I HO-(-H I H-(-OH I H-(-OH I (H2 0H XLIII (=0 I (H2 H-~-O I AcNH-(-H I HO-(-H I H-(-OH I H-(-OH I (H2 0H ow ) NAN A XXVII FIGURE 12.
The recent report of Buscher et al. (1974), in which three new sialic acids were described, presents a combination of methods that together comprise a powerful tool for separating and characterizing the components of complex mixtures. TLC in two dimensions with intermediate ammonia treatment to remove O-acyl groups led to identification of the basic N-acylneuraminic acids, while substitution of hydroxylamine for ammonia permitted identification of the O-acyl groups as hydroxamates. By this means two sialic acids containing an O-glycolyl group were 15 Chemistry and Analysis of Sialic Acid characterized for the first time.
The sign and location of ellipticity bands for sialic acid and its derivatives were found to depend on the state of the carboxyl group (free versus esterified) and the nature of the solvent (Ledeen, 1970; Dickinson and Bush, 1975). Additional influence is exerted by the grouping to which sialic acid is 22 R. W. Ledeen and R. K. Yu ketosidically linked, as shown in the distinguishable CD patterns obtained for the (2~3) and (2~6) isomers of neuraminosyllactose (Dickinson and Bush, 1975). C. Chemical Reactions and Derivatives Sialic acids are highly reactive toward many reagents, and the diversity of products can be understood in terms of the nature and orientation of the various functional groups.