Chemoenzymic synthesis of an original arabinofuranosyl cluster: optimization of the enzymatic conditions. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue ARKIVOC - Online Journal of Organic Chemistry Année : 2013

Chemoenzymic synthesis of an original arabinofuranosyl cluster: optimization of the enzymatic conditions.

Résumé

The evaluation of a mutated glycosidase as a major, renewable and eco-friendly partner (green chem. method) of a glycosylation reaction permitted a one-step synthesis of an arabinofuranosyl cluster in 38% yield. A mutated biocatalyst was able to perform coupling to a multivalent bulky substituent with 80% yield on each arm and pave the way for the further development of enzymic means of ligation of carbohydrates onto org. scaffolds. The title compd. thus formed was a tetramer (I) [i.e., 4-[(α-L-arabinofuranosyl)thio]benzeneacetic acid 2,2-bis[[[[4-[(α-L-arabinofuranosyl)thio]phenyl]acetyl]oxy]methyl]-1,3-propanediyl ester]. The synthesis of the target compd. was achieved by a reaction of 4-(mercapto)benzeneacetic acid 2,2-bis[[[(4-mercaptophenyl)acetyl]oxy]methyl]-1,3-propanediyl ester with 1H-benzimidazol-2-yl 1-thio-α-L-arabinofuranoside. [on SciFinder(R)]

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Autre

Dates et versions

hal-01069719 , version 1 (29-09-2014)

Identifiants

Citer

Melanie Almendros, Marc Francois-Heude, Laurent Legentil, Caroline Nugier-Chauvin, Richard Daniellou, et al.. Chemoenzymic synthesis of an original arabinofuranosyl cluster: optimization of the enzymatic conditions.. ARKIVOC - Online Journal of Organic Chemistry, 2013, pp.123--132. ⟨10.3998/ark.5550190.0014.211⟩. ⟨hal-01069719⟩
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