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Significant substituent effect on the anomerization of pyranosides: Mechanism of anomerization and synthesis of a 1,2-cis glucosamine oligomer from the 1,2-trans anomer


Manabe, Shino; Satoh, Hiroko; Hutter, Juerg; Luethi, Hans Peter; Laino, Teodoro; Ito, Yukishige (2014). Significant substituent effect on the anomerization of pyranosides: Mechanism of anomerization and synthesis of a 1,2-cis glucosamine oligomer from the 1,2-trans anomer. Chemistry - A European Journal, 20(1):124-132.

Abstract

Aminoglycosides containing a 2,3-trans carbamate group easily undergo anomerization from the 1,2-trans glycoside to the 1,2-cis isomer under mild acidic conditions. The N-substituent of the carbamate has a significant effect on the anomerization reaction; in particular, an N-acetyl group facilitated rapid and complete -anomerization. The differences in reactivity due to the various N-substituents were supported by the results of DFT calculations; the orientation of the acetyl carbonyl group close to the anomeric position was found to contribute significantly to the directing of the anomerization reaction. By exploiting this reaction, oligoaminoglycosides with multiple 1,2-cis glycosidic bonds were generated from 1,2-trans glycosides in a one-step process.

Abstract

Aminoglycosides containing a 2,3-trans carbamate group easily undergo anomerization from the 1,2-trans glycoside to the 1,2-cis isomer under mild acidic conditions. The N-substituent of the carbamate has a significant effect on the anomerization reaction; in particular, an N-acetyl group facilitated rapid and complete -anomerization. The differences in reactivity due to the various N-substituents were supported by the results of DFT calculations; the orientation of the acetyl carbonyl group close to the anomeric position was found to contribute significantly to the directing of the anomerization reaction. By exploiting this reaction, oligoaminoglycosides with multiple 1,2-cis glycosidic bonds were generated from 1,2-trans glycosides in a one-step process.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2014
Deposited On:17 Oct 2014 11:26
Last Modified:05 Apr 2016 17:29
Publisher:Wiley-VCH Verlag Berlin
ISSN:0947-6539
Publisher DOI:https://doi.org/10.1002/chem.201303474
PubMed ID:24307501

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