Synthesis and X-ray crystallographic investigation of N-(β-d-glycosyl)butanamides derived from GlcNAc and chitobiose as analogs of the conserved chitobiosylasparagine linkage of N-glycoproteins

Mathiselvam, Manoharan; Srivastava, Amrita; Varghese, Babu; Pérez, Serge; Loganathan, Duraikkannu

doi:10.1016/j.carres.2013.07.004

Carbohydrate Research

2013

DOI: 10.1016/j.carres.2013.07.004

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Synthesis and X-ray crystallographic investigation of N-(β-d-glycosyl)butanamides derived from GlcNAc and chitobiose as analogs of the conserved chitobiosylasparagine linkage of N-glycoproteins

Manoharan Mathiselvam

Amrita Srivastava

Babu Varghese

et al.

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Cited by 5 publications

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“…[1] Currently its hydrolysis is widely used for the industrial production of the glucosamine monomer, and to a much lessser extent, the production of chitooligosaccharides (COSs), because of low production yields of often heterogeneous mixtures. Furthermore, the degradation of chitin by acetolysis is well documented, [2,3] and leads only to or mainly to the dimer [2] as well as the tri-and tetramer being isolated in poor yield. [3] Higher oligomers exhibit numerous biological activities [4,5] and their elaboration to size-defined molecules with distinct substitution patterns is greatly desirable.…”

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confidence: 99%

From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG‐chitotriomycin

et al. 2014

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The direct and chemoselective N-transacylation of peracetylated chitooligosaccharides (COSs), readily obtained from chitin, to give per-N-trifluoroacetyl derivatives offers an attractive route to size-defined COSs and derived glycoconjugates. It involves the use of various acceptor building blocks and trifluoromethyl oxazoline dimer donors prepared with efficiency and highly reactive in 1,2-trans glycosylation reactions. This method was applied to the preparation of the important symbiotic glycolipids which are highly active on plants and to the TMG-chitotriomycin, a potent and specific inhibitor of insect, fungal, and bacterial N-acetylglucosaminidases.

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confidence: 99%

From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG‐chitotriomycin

et al. 2014

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From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG‐chitotriomycin

Despras¹,

Alix²,

Urban³

et al. 2014

Angewandte Chemie

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The direct and chemoselective N‐transacylation of peracetylated chitooligosaccharides (COSs), readily obtained from chitin, to give per‐N‐trifluoroacetyl derivatives offers an attractive route to size‐defined COSs and derived glycoconjugates. It involves the use of various acceptor building blocks and trifluoromethyl oxazoline dimer donors prepared with efficiency and highly reactive in 1,2‐trans glycosylation reactions. This method was applied to the preparation of the important symbiotic glycolipids which are highly active on plants and to the TMG‐chitotriomycin, a potent and specific inhibitor of insect, fungal, and bacterial N‐acetylglucosaminidases.

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Effect of distal sugars and interglycosidic linkage on the N-glycoprotein linkage region conformation: synthesis and X-Ray crystallographic investigation of β-1-N-alkanamide derivatives of cellobiose and maltose as disaccharide analogs of the conserved chitobiosylasparagine linkage

et al. 2013

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The linkage region constituents, 2-deoxy-2-acetamido-β-D-glucopyranose (GlcNAc) and L-asparagine (Asn) are conserved in the N-glycoproteins of all eukaryotes. Elucidation of the structure and conformation of the linkage region of glycoproteins is important to understand the presentation and dynamics of the carbohydrate chain at the protein/cell surface. Earlier crystallographic studies using monosaccharide models and analogs of N-glycoprotein linkage region have shown that the N-glycosidic torsion, ϕN, is more influenced by the structural variation in the sugar part than that of the aglycon moiety. To access the influence of distal sugar as well as interglycosidic linkage (α or β) on the N-glycosidic torsion angles, cellobiosyl and maltosyl alkanamides have been synthesized and structural features of seven of these analogs have been characterized by X-ray crystallography. Comparative analysis of the seven disaccharide analogs with the reported monosaccharide analogs showed that the ϕN value of cellobiosyl analogs deviate ~9° with respect to GlcβNHAc. In the case of maltosyl analogs, deviation is more than 18°. These deviations indicate that the N-glycosidic torsion is influenced by addition of distal sugar as well as with respect to inter glycosidic linkage (α or β); it is less influenced by changes occurring at the aglycon. The χ₂ value of alkanamide derived from glucose, cellobiose and maltose exhibit a large range of variations (from 1.6° to -109.9°). This large span of χ₂ value suggests the greater degree of rotational freedom around C1'-C2' bond which is restricted in GlcNAc alkanamides. The present finding explicitly proved the importance of molecular architecture in the N-glycoproteins linkage region to maintain the linearity, planarity and rigidity. These factors are necessary for N-glycan to serve role in inter- as well as intramolecular carbohydrate-protein interactions.

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Synthesis and X-ray crystallographic investigation of N-(β-d-glycosyl)butanamides derived from GlcNAc and chitobiose as analogs of the conserved chitobiosylasparagine linkage of N-glycoproteins

Cited by 5 publications

References 19 publications

From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG‐chitotriomycin

From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG‐chitotriomycin

From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG‐chitotriomycin

Effect of distal sugars and interglycosidic linkage on the N-glycoprotein linkage region conformation: synthesis and X-Ray crystallographic investigation of β-1-N-alkanamide derivatives of cellobiose and maltose as disaccharide analogs of the conserved chitobiosylasparagine linkage

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