The Thioglycoside and Glycosyl Phosphite of 5-Azido Sialic Acid: Excellent Donors for theα-Glycosylation of Primary Hydroxy Groups

Yu, Chung‐Shan; Niikura, Kenichi; Lin, Chun‐Cheng; Wong, Chi‐Huey

doi:10.1002/1521-3773(20010803)40:15<2900::aid-anie2900>3.0.co;2-4

Cited by 131 publications

(68 citation statements)

References 36 publications

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“…24 Some of these strategies have been successfully used in oligo-sialic acid synthesis. 25–30 Notably, an α-2,9-dodecasialic acid was effectively prepared with N 5 , O 4 -carbonyl-protected α-sialyl phosphate as a sialyl donor. 31 However, most of the reported α-2,9-oligosialic acids were not completely deprotected and coupled with carrier proteins to form conjugate vaccines.…”

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confidence: 99%

Synthesis and immunological study of α-2,9-oligosialic acid conjugates as anti-group C meningitis vaccines

2015

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mentioning

confidence: 99%

Synthesis and immunological study of α-2,9-oligosialic acid conjugates as anti-group C meningitis vaccines

2015

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“…3) (21)(22)(23). Following reports where the building blocks carry various C-5 amino groups including azide, cyclic imide and carbamate protections show promising results (24)(25)(26)(27). N-Tri chloroethoxycarbonyl (Troc) protections have been especially investigated because of the favorable stability under the conditions used for glycosylation and the various protecting group manipulations (28,29).…”

Section: N-5 Modifi Ed Sialic Acid Building Blocksmentioning

confidence: 99%

Recent Strategies for Stereoselective Sialylation and Their Application to the Synthesis of Oligosialosides

Hanashima

2011

TIGG

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S i a l i c a c i d s o n t h e n o n -r e d u c i n g t e r m i n u s o f sialylgylcans are abundantly expressed on the surface of mammalian cells. They play vital roles in cell-cell interactions and during infection by pathogenic bacteria and viruses. The chemical synthesis of sialylated glycans has been investigated for more than two decades, and interesting chemistry has been developed for coupling of sialic acid in an α-selective manner. Chemoenzymatic approaches are also now available for stereoselective sialylations. This mini-review focuses on very recent advances in stereoselective chemical sialylations and synthesis of natural sialylglycans using novel strategies, especially for the synthesis of the oligo/polysialic acid structure.

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“…However, α-selective sialylation is a problematic step in the chemical synthesis of oligosaccharides. Recently, it was found that replacement of the acetylamino group at the 5 position of the sialyl donor with an N,N-diacetyl (22), azido (23) of various sialo-containing oligosaccharides.…”

Section: C-3 Synthesis Of Sialo-containing Glycosyl Amino Acids By Omentioning

confidence: 99%

Rapid Synthesis of Oligosaccharides Based on One-Pot Glycosylation

Tanaka

Yamada

Takahashi

2007

TIGG

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In this study, biologically active oligosaccharides were synthesized based on one-pot glycosylation. Onepot glycosylation enables direct coupling of multisaccharide building blocks via sequential chemo-and regioselective glycosylations in a single vessel. A di-branched heptasaccharide was synthesized by one-pot glycosylation using seven independent building blocks. The glycosyl amino acids containing sialic acids were covered by the onepot glycosylation, in which sialylation was achieved with N-Troc-protected thiosialoside. Combinatorial oligosaccharide libraries were synthesized by one-pot glycosylation using parallel and automated synthesizers. This study also developed a polymer-assisted strategy for deprotection of protected oligosaccharides. A. IntroductionOligosaccharides play important roles in cell surface events via carbohydrate-protein and carbohydrate-carbohydrate interactions (1). The ability to chemically synthesize structurally defined oligosaccharides for structure-function studies is highly advantageous because oligosaccharides from natural sources are available only in limited quantities. Recent progress in oligosaccharide synthesis has resulted in a number of new and efficient glycosidation methodologies ( 2 ) . H o w e v e r, o l i g o s a c c a h r i d e s y n t h e s e s i n v o l v i n g glycosylation and deprotection are difficult to achieve using standard protocols and require well-trained organic chemists. Seeberger and co-workers reported an automated solid-phase oligosaccharide synthesis using a modified solid-phase peptide synthesizer (3). Alternatively, one-pot sequential glycosylation for the synthesis of oligosaccharides was demonstrated by Kahne and co-workers in 1993. In this method an α-linked deoxytrisaccahride was prepared by sequential chemoselective activation of glycosyl sulfoxide and thioglycoside using a single activator (4). One-pot glycosylation enables coupling of multiple building blocks in a single vessel to yield oligosaccharides; the reaction protocols are simple, involving

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The Thioglycoside and Glycosyl Phosphite of 5-Azido Sialic Acid: Excellent Donors for theα-Glycosylation of Primary Hydroxy Groups

Cited by 131 publications

References 36 publications

Synthesis and immunological study of α-2,9-oligosialic acid conjugates as anti-group C meningitis vaccines

Synthesis and immunological study of α-2,9-oligosialic acid conjugates as anti-group C meningitis vaccines

Recent Strategies for Stereoselective Sialylation and Their Application to the Synthesis of Oligosialosides

Rapid Synthesis of Oligosaccharides Based on One-Pot Glycosylation

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