ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Confomational Analysis, XXIV. - determination of the Conformations of Tri-and Tetrasaccharide Sequences of N-Glycoproteins. The problem of the (1 → 6)-glycosidic BondThe preferred solution conformations of the saccharides α-D-Man(1 → 3)-β-D-Man(1 → 4)-D-GIcNAc (1), α-D-Man(1 → 6)-β-Man(1 → 4)-D-GIcNAc (2), and α-D-Man(1 → 3)[α-D-Man(1 → 6)]lβ-D-Man(1 → 4)-D-GIcNAc3), which are known as parts of the core structure of N-glycoproteins, could be established by use of HSEA calculations (HSEA: Hard-Sphere Exo-Anomeric) with the new program GESA (= Geometry of Saccharides) in connection with 1H NMR investigations like NOE experiments, spin-lattice relaxation-time measurements and the observation of selective deshieldings. (1 → 3)- and (1 → 4)-glycosidic bonds show one strongly preferred conformation. The greater flexibility of the (1 → 6)-glycosidic bonds show one strongly preferred conformation. The greater flexibility of the (1 → 6)-glycosidic bond will be discussed in details. For the spectra analysis various 2-D techniques have been used.
Notes:
Von den Sacchariden α-D-Man(1 → 3)-β-D-Man(1 → 4)-D=-GICNAc (1), α-D-Man(1 → 6)-β-D-Man(1 → 4)-D-GIcNAc(2) und α-D-Man(1 → 3)[α-D-Man(1 → 6)]-β-D-Man(1 → 4)-D-GlcNAc(3), die als Core-Struktur in N-Glycoproteinen vorkommen, wurden durch HSEA-Berechnungen (HSEA: Hard-Sphere Exo-Anomeric) mit dem neuen GESA-Programm (GESA: Geometry of Saccharides) die bevorzugten Konformationen bestimmt. Mit Hilfe von 1H-NMR-Experimenten, nämlich NOE-Experimenten, Spin-Gitter-Relaxationszeitmessungen und der Beobachtung selektiver Entschirmungen, ließen sich diese Konformationen in Lösung bestätigen. (1 → 3)- und (1 → 4)-glycosidische Bindungen weisen eine stark bevorzugte Konformation auf. Die weitaus größere Flexibilität der (1 → 6)-glycosidischen Bindung wird besonders diskutiert. Zur Analyse der Spektren wurden verschiedene 2-D-NMR-Techniken angewandt.
Additional Material:
10 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198419840514
