Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/30945
COMPARTIR / EXPORTAR:
logo share SHARE logo core CORE BASE
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE

Invitar a revisión por pares abierta
Título

Experimental Evidence for the Existence of Non-exo-Anomeric Conformations in Branched Oligosaccharides: NMR Analysis of the Structure and Dynamics of Aminoglycosides of the Neomycin Family

AutorAsensio, Juan Luis CSIC ORCID; Hidalgo, Ana; Cuesta, Igor CSIC; González, Carlos CSIC ; Cañada, F. Javier ; Vicent, Cristina CSIC ORCID; Chiara, José Luis CSIC ORCID ; Cuevas, Gabriel; Jiménez-Barbero, Jesús CSIC ORCID
Palabras claveAnomeric effect
Antibiotics
Molecular dynamics
Molecular recognition
NMR spectroscopy
Fecha de publicaciónnov-2002
EditorWiley-Blackwell
CitaciónChemistry - A European Journal 8(22): 5228-5240 (2002)
ResumenIt is commonly known that the exo-anomeric effect is a major factor governing the conformational behavior of naturally occurring oligosaccharides. Conformational flexibility in these molecules mainly concerns the aglycon ψ angle since ϕ is restricted by this stereoelectronic effect. In fact, to the best of our knowledge no case of a natural glycoside adopting a non-exo-anomeric conformation in solution has yet been reported. With respect to the flexibility among naturally occurring carbohydrates, branched type oligosaccharides including sugar residues glycosidated at contiguous positions (such as blood type carbohydrate antigens Lewis X) have been considered as the paradigm of rigid saccharides—the rigidity being enhanced by van der Waals interactions. Herein, we demonstrate unambiguously that both common beliefs are not to be generalized. For example in neomycin B, a branched oligosaccharide antibiotic, a large number of non-exo-anomeric conformations was detected in solution for the first time in naturally occurring sugars. This unusual behavior is attributed to branching. Here, polar contacts between non-vicinal sugar units lead to an enhanced flexibility of the ribose glycosidic torsion ϕ. The influence of sugar flexibility on RNA recognition will also be discussed.
Descripción13 páginas, 14 figuras, 2 tablas.-- Supporting information for this article (Figures showing details of the NMR analysis n and ribostamycin) is available on the WWW under http://www.chemeurj.org or from the author.
Versión del editorhttp://dx.doi.org/10.1002/1521-3765(20021115)8:22<5228::AID-CHEM5228>3.0.CO;2-L
URIhttp://hdl.handle.net/10261/30945
DOI10.1002/1521-3765(20021115)8:22<5228::AID-CHEM5228>3.0.CO;2-L
ISSN0947-6539
Aparece en las colecciones: (IQOG) Artículos
(CIB) Artículos
(CFMAC-IEM) Artículos

Mostrar el registro completo

CORE Recommender

SCOPUSTM   
Citations

22
checked on 24-mar-2024

Page view(s)

361
checked on 28-mar-2024

Google ScholarTM

Check

Altmetric

Altmetric


NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.