The Chemistry of Sialic Acid

Boons, Geert‐Jan; Demchenko, Alexei V.

doi:10.1002/3527602437.ch3

Cited by 24 publications

(12 citation statements)

References 187 publications

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“…131 A great deal of effort has been devoted to the synthesis of the α-sialosides but their stereocontrolled synthesis still represents a formidable challenge to the synthetic chemist. The area has been reviewed a number of times 132 and we concentrate here only on recent advances using cyclic protecting groups.…”

Section: α-Sialosidesmentioning

confidence: 99%

Methodology Development and Physical Organic Chemistry: A Powerful Combination for the Advancement of Glycochemistry

Crich

2011

J. Org. Chem.

111

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Section: α-Sialosidesmentioning

confidence: 99%

Methodology Development and Physical Organic Chemistry: A Powerful Combination for the Advancement of Glycochemistry

Crich

2011

J. Org. Chem.

111

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“…[1] For the most part advances have centered around modification of the N-5 protecting group, [2] culminating in the discovery of the 4- O -,5- N -oxazolidine systems [3] and their N -acetyl variants, [3c, 4] which afford excellent yields and selectivities. Nevertheless, the potential applications of sialic acid glycosides and their oligomers in medicine, [5] and the consequent need for larger scale synthesis, drive the continued search for improved methods.…”

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confidence: 99%

The Isothiocyanato Moiety: An Ideal Protecting Group for the Stereoselective Synthesis of Sialic Acid Glycosides and Subsequent Diversification

et al. 2014

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The preparation of a crystalline, peracetyl adamantanyl thiosialoside donor protected by an isothiocyanate group is described. On activation at -78 C in the presence of typical carbohydrate acceptors this donor gives high yields of the corresponding sialosides with exquisite α-selectivity. The high selectivity extends to the 4-O-benzyl-protected 3-OH acceptors that are typically less reactive and selective than galactose 3,4-diols. Treatment of the α-sialosides with tris(trimethylsilyl)silane or allyltris(trimethylsilyl)silane sialosides replaces the C5-N5 bond by a C-H or a C-C bond. Reaction of the isothiocyanate-protected sialosides with thioacids achieves conversion into amides. Reaction of the isothiocyanate with an amine gives a thiourea, which can be converted to a guanidine. The very high α-selectivities observed with the new donor and the rich chemistry of the isothiocyante function considerably extend the scope for optimization at the sialoside 5-position.

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“…6,107,137,660,[666][667][668][669][670][671][672] Furthermore, the progress in the biotechnology of carbohydrate enzymes led also to the generation of suitable amounts of stereoselective sialyltransferases/CMP-Neu5Acyl and trans-sialidases, which made enzymatic approaches attractive. 107,126,137,139,142,660,669,[673][674][675][676] In this way, growing activities focused on a further exploration of the properties of modified sialic acids, the preparation of substrates and inhibitors for sialidases, sialyltransferases, trans-sialidases, or sialic acid-converting enzymes, the synthesis of sialo-glycans, and to make compounds accessible for analytical purposes or for studies related to metabolism or biological functions of sialic acids. Over the years, several detailed reviews, describing different aspects of sialic acid organic and enzymatic synthesis, were published (see references in the foregoing paragraphs of this section).…”

Section: Growing Interest From the Organic And Enzymatic Chemistrymentioning

confidence: 99%

Exploration of the Sialic Acid World

Schauer

Kamerling

2018

Advances in Carbohydrate Chemistry and Biochemistry

248

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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The Chemistry of Sialic Acid

Cited by 24 publications

References 187 publications

Methodology Development and Physical Organic Chemistry: A Powerful Combination for the Advancement of Glycochemistry

Methodology Development and Physical Organic Chemistry: A Powerful Combination for the Advancement of Glycochemistry

The Isothiocyanato Moiety: An Ideal Protecting Group for the Stereoselective Synthesis of Sialic Acid Glycosides and Subsequent Diversification

Exploration of the Sialic Acid World

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