Zur Biosynthese der Glykolyl-Gruppe der N-Glykolyl-neuraminsäure. Die oxydative Umwandlung der N-Acetyl-Gruppe zur Glykolyl-Gruppe

Schauer, Roland; Schoop, Hans Joseph; Faillard, Hans

doi:10.1515/bchm2.1968.349.1.645

Cited by 33 publications

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“…The predominant types of Sias in mammals include N -acetylneuraminic acid (Neu5Ac) and its hydroxylated version, Neu5Gc (Figure 1). These two molecules differ by a single oxygen atom, which is added to CMP-Neu5Ac in the cytosol, via a reaction catalyzed by the enzyme cytidine monophosphate N -acetylneuraminic acid hydroxylase (CMAH) (37–44). These activated sugars are then transported into the Golgi, where they act as donors for various sialyltransferases.…”

Section: Diversity In the Sialic Acidsmentioning

confidence: 99%

Involvement of a Non-Human Sialic Acid in Human Cancer

et al. 2014

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Sialic acids are common monosaccharides that are widely expressed as outer terminal units on all vertebrate cell surfaces, and play fundamental roles in cell–cell and cell–microenvironment interactions. The predominant sialic acids on most mammalian cells are N-glycolylneuraminic acid (Neu5Gc) and N-acetylneuraminic acid (Neu5Ac). Neu5Gc is notable for its deficiency in humans due to a species-specific and species-universal inactivating deletion in the CMAH gene encoding the hydroxylase that converts CMP-Neu5Ac to CMP-Neu5Gc. However, Neu5Gc is metabolically incorporated into human tissues from dietary sources (particularly red meat), and detected at even higher levels in some human cancers. Early life exposure to Neu5Gc-containing foods in the presence of certain commensal bacteria that incorporate dietary Neu5Gc into lipooligosaccharides can lead to generation of antibodies that are also cross-reactive against Neu5Gc-containing glycans in human tissues (“xeno-autoantigens”). Such anti-Neu5Gc “xeno-autoantibodies” are found in all humans, although ranging widely in levels among individuals, and displaying diverse and variable specificities for the underlying glycan. Experimental evidence in a human-like Neu5Gc-deficient Cmah−/−mouse model shows that inflammation due to “xenosialitis” caused by this antigen–antibody interaction can promote tumor progression, suggesting a likely mechanism for the well-known epidemiological link between red meat consumption and carcinoma risk. In this review, we discuss the history of this field, mechanisms of Neu5Gc incorporation into tissues, the origin and specificities of human anti-Neu5Gc antibodies, their use as possible cancer biomarkers, implications of xenosialitis in cancer initiation and progression, and current and future approaches toward immunotherapy that could take advantage of this unusual human-specific phenomenon.

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Section: Diversity In the Sialic Acidsmentioning

confidence: 99%

Involvement of a Non-Human Sialic Acid in Human Cancer

et al. 2014

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“…Ever since the discovery, in porcine submandibular gland mucin, of large quantities of Neu5Gc, and high amounts of O-acetylated Sia in bovine submandibular glands [5±9], we have taken an interest in the metabolism of these Sia. The oxidative conversion of the N-acetyl group of Neu5Ac to the N-glycolyl residue of Neu5Gc had already been observed in 1968 in surviving slices of pig submandibular glands [31]. However, it took until 1988 to determine the substrate for this reaction, that being CMP-Neu5Ac [32].…”

Section: Biosynthesis Of Sialic Acidsmentioning

confidence: 99%

Untitled

Schauer

2000

Glycoconjugate Journal

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514

205

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Slalic acids are one of the most important molecules of life, since they occupy the terminal position on macromolecules and cell membranes and are involved in many biological and pathological phenomena. The structures of sialic acids, comprising a family of over 40 neuraminic acid derivatives, have been elucidated. However, many aspects of the regulation of their metabolism at the enzyme and gene levels, as well as of their functions remain mysterious. Sialic acids play a dual role, not only are they indispensable for the protection to and adaptation of life, but are also utilised by life-threatening infectious microorganisms. In this article the present state of knowledge in sialobiology, with an emphasis on my personal experience in this research area, is outlined including a discussion of necessary future work in this fascinating field of cell biology.

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“…808 Further incubations with [1-14 C]acetate, N-[1-14 C]acetyl-mannosamine, and N-[1-14 C]acetyl-neuraminic acid led in each case to the identification of N-[1-14 C]glycolyl-neuraminic acid. [809][810][811] All these results led to the claim of the existence of an N-acetylhydroxylase, involved in Neu5Gc biosynthesis. Most of the newly formed, radioactive Neu5Gc was within the tissue still free and not yet incorporated into glycoconjugates.…”

Section: N-glycolylneuraminic Acidmentioning

confidence: 99%

Exploration of the Sialic Acid World

Schauer

Kamerling

2018

Advances in Carbohydrate Chemistry and Biochemistry

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261

225

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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

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Zur Biosynthese der Glykolyl-Gruppe der N-Glykolyl-neuraminsäure. Die oxydative Umwandlung der N-Acetyl-Gruppe zur Glykolyl-Gruppe

Cited by 33 publications

References 0 publications

Involvement of a Non-Human Sialic Acid in Human Cancer

Involvement of a Non-Human Sialic Acid in Human Cancer

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Exploration of the Sialic Acid World

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