Exploration of the Sialic Acid World

Abstract

The Sialic Acid World Table 1 Survey of Reported Structures of Naturally Occurring Members of the Sialic Acid Family-cont'd Name Abbreviation References5-N-Acetyl-8-O-acetyl-9-Olactyl-neuraminic acid Neu5,8Ac 2 9Lt 45 5-N-Acetyl-8-O-methylneuraminic acid Neu5Ac8Me 6,19,25,33,46 5-N-Acetyl-4-O-acetyl-8-Omethyl-neuraminic acid Neu4,5Ac 2 8Me 19 5-N-Acetyl-9-O-acetyl-8-Omethyl-neuraminic acid Neu5,9Ac 2 8Me 6,19,33,46 5-N-Acetyl-9-O-methylneuraminic acid Neu5Ac9Me 47 5-N-Acetyl-4-O-sulfoneuraminic acid Neu5Ac4S 48 5-N-Acetyl-8-O-sulfoneuraminic acid Neu5Ac8S 19,32,49,50 5-N-Acetyl-4-O-acetyl-8-Osulfo-neuraminic acid Neu4,5Ac 2 8S 19 5-N-Acetyl-9-O-phosphoneuraminic acid f,g Neu5Ac9P 51 5-N-Acetyl-2-deoxy-2,3didehydro-neuraminic acid g,h Neu2en5Ac 6,30,33,43,52-54 5-N-Acetyl-9-O-acetyl-2deoxy-2,3-didehydroneuraminic acid g Neu2en5,9Ac 2 55,56 5-N-Acetyl-2-deoxy-2,3didehydro-9-O-lactylneuraminic acid g Neu2en5Ac9Lt 55,565-N-Acetyl-2,7-anhydroneuraminic acid g,i

Sialic acid and biology of life: An introduction

“…[3]. In the still growing family of sialic acids, >50 different derivatives [3,5,42] ( Table 1) have been reported of which the two most commonly expressed members of sialic acid family are Neu5Ac and Neu5Gc followed by KDN (2-keto-3-deoxy-nononic acid) and Neu (neuraminic acid) [43].…”

“…4) [82] . Table 1 Naturally occurring sialic acid family members [5,[83][84][85][86][87][88] Name Abbreviation 5-N-Acetyl-4,9-di-O-acccyl-neuraminic acid 1,7-lactone Neu4,5,9Ac 3 1,7lactone 1-Tauryl 5-N-acetyl-neuraminic amide Continued Table 1 Naturally occurring sialic acid family members [5,[85][86][87][88][89][90] Adapted with permission from Schauer R, Kamerling JP. Exploration of sialic acid world Chapter 1, Advances in carbohydrate chemistry and biochemistry, vol.…”

“…Sialic acid family has now been designated as subclass of the superfamily of naturally occurring non-2-ulosonic acids (NulOs), the parent molecule of the family being neuraminic acid (Neu), which is not found in free form in nature due to its immediate cyclization to form an internal Schiff base, and is a nine-carbon-containing monosaccharide, comprising 2-keto-carboxylic acid, a deoxysugar, and an aminosugar. Other members of the NulO superfamily include 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids, with the mother molecules pseudaminic acid (Pse), legionaminic acid (Leg), 4-epi-legionaminic acid (4eLeg), 8-epilegionaminic acid (8eLeg), acinetaminic acid (Aci), and 8-epi-acinetaminic acid (8eAci), found in bacterial polysaccharides and glycoproteins [5] (Fig. 6).…”

“…The negative charge and hydrophilic properties of sialic acid enable its role in different normal and pathological processes, acting as binding sites for various pathogens and toxins wherein pathogen-binding protein recognizes sialic acids present in specific linkages which are thought to have evolved in vertebrates through evolution. Molecular mimicry exhibited by pathogens, by decorating with sialic acids, has been known to enable them to evade the host immune system [1][2][3][4][5][6][10][11][12].…”

“…Sialic acid content of the human brain is the highest among other organisms, and may be associated with evolutionary advancement of an organism [1][2][3][4][5][6][13][14][15][16][17][18]. In Neu5Gc or N-glycolylneuraminic acid, the terminal sialic acid residue is linked by the hydroxy group of the glycolic acid unit, synthesized from Neu5Ac catalyzed by CMP-N-acetylneuraminic acid (CMP-Neu5Ac) hydroxylase (CMAH) in animals including lower animals [19][20][21][22].…”