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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, Babu Varghese, Duraikkannu Loganathan
Published in Elsevier Ltd
2013
PMID: 23916853
Volume: 380
   
Pages: 37 - 44
Abstract
The linkage region, GlcNAcβAsn, is conserved in all eukaryotic N-glycoproteins. As a logical extension of a research endeavor aimed at understanding the structural significance of GlcNAc and Asn as the linkage region constituents, the newer analogs GlcNAcβNHBu and (GlcNAcβ(1-4) GlcNAc)alkanamides have been synthesized to assess the influence of aglycon as well as additional GlcNAc on the linkage region. X-ray crystallographic analysis of the GlcNAcβNHBu and (GlcNAcβ(1-4)GlcNAc)βNHBu is described. Comparative analysis of these structures with those of reported models and analogs shows that the deviation in N-glycosidic torsion, φN among the GlcNAc alkanamides is negligible (<2) whereas (GlcNAcβ(1-4) GlcNAc)βNHBu deviates by ∼15 as compared to GlcNAcβNHBu. Under the influence of the molecular packing, the conformation around the C1′-C2′ bond deviates from anti to gauche in (GlcNAcβ(1-4) GlcNAcβNHBu. Interestingly, C2-acetamido group in (GlcNAcβ(1-4)GlcNAc) NHBu orients differently as compared to GlcNAc alkanamides and this orientation was found to be almost similar to β-N,N′-diacetylchitobiose trihydrate. The bifurcated anti-parallel pattern involving N-HO and C-HO hydrogen bonds, a hallmark feature of the N-glycoprotein models, GlcNAcβNHAc and GlcNAcβAsn, is absent in both the title alkanamides. This is the first report on the crystal structure analysis of chitobiosyl alkanamide as analog of the N-glycoprotein linkage region, (GlcNAcβ(1-4) GlcNAc)βAsn. © 2013 Published by Elsevier Ltd.
About the journal
JournalData powered by TypesetCarbohydrate Research
PublisherData powered by TypesetElsevier Ltd
ISSN00086215
Open AccessNo
Concepts (56)
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    C (programming language)
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    Hydrogen bonds
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    X ray crystallography
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    X rays
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    ANALOGS
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    Comparative analysis
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    Crystal structure analysis
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    LINKAGE REGION
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    MOLECULAR ASSEMBLY
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    MOLECULAR PACKINGS
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    N-GLYCOPROTEIN
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    X-ray crystallographic analysis
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    Glycoproteins
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    Acetamide derivative
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    AGLYCONE
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    Alkane derivative
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    ASPARAGINE DERIVATIVE
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    Carbon
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    CHITOBIOSE
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    CHITOBIOSYLASPARAGINE
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    Glycoprotein
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    Hydrogen
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    N acetylglucosamine
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    N GLYCOPROTEIN
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    Nitrogen
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    Oxygen
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    Unclassified drug
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    Article
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    Chemical modification
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    Controlled study
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    Covalent bond
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    Cross linking
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    Crystal structure
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    Hydrogen bond
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    Molecular dynamics
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    Priority journal
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    Protein analysis
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    Protein conformation
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    Protein glycosylation
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    Protein synthesis
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    Proteomics
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    Eukaryota
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    ANALOGS
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    LINKAGE REGION
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    N-GLYCOPROTEIN
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    X-RAY AND MOLECULAR ASSEMBLY
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    ACETYLGLUCOSAMINE
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    Amides
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    Asparagine
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    Carbohydrate conformation
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    Chemistry techniques, synthetic
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    Conserved sequence
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    Crystallography, x-ray
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    Disaccharides
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    Glycosylation
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    Molecular conformation