Synthesis and High-Field NMR of α-D-Arabinofuranosyl-(1→6)-2-AcetamidO-2-Deoxy-O-D-Glucopyranosyl-(1→3)-6-Deoxy-L-Talose, the Repeating Unit of an O-Specific Lipopolysaccharide fromPseudomonasMaltophiliaN.C.I.B. 9204
作者:
András Lipták,
János Kerékgyártó,
Velimir Popsavin,
Maria Kajtár-Peredy,
Lajos Radies,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1988)
卷期:
Volume 7,
issue 2
页码: 337-357
ISSN:0732-8303
年代: 1988
DOI:10.1080/07328308808058929
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Starting from L-rhamnose, benzyl 2,4-di-O-benzyl-6-deoxy-α-L-talopyranoside (7) was prepared by hydrogenolysis of a dioxolane-type benzylidene acetal and used as the aglycon to prepare 2-acetamido-2-deoxy-6-D-glucopyranosyl-(1–3)-6-deoxy-L-talose (13) and the title trisacchafide (20). Due to fast interconvirsion between the α-, β- -pyranose/furanose forms at the reducing end of the molecule in aqueous solutions, the di- and trisaccharides occur as mixtures of four isomers all in significant concentration. By two-dimensional (20) methods, the proton (400) and carbon (100 MHz) NMR spectra of the individual tri-saccharide isomers were completely assigned and interpreted in terms of stereochemistry of the 6-deoxy-L-talose residue.
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