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Expedient synthesis of C-aryl carbohydrates by consecutive biocatalytic benzoin and aldol reactions.
Expedient synthesis of C-aryl carbohydrates by consecutive biocatalytic benzoin and aldol reactions.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2015 Feb 16; Vol. 21 (8), pp. 3335-46. Date of Electronic Publication: 2015 Jan 07. - Publication Year :
- 2015
-
Abstract
- The introduction of aromatic residues connected by a C-C bond into the non-reducing end of carbohydrates is highly significant for the development of innovative structures with improved binding affinity and selectivity (e.g., C-aril-sLex). In this work, an expedient asymmetric "de novo" synthetic route to new aryl carbohydrate derivatives based on two sequential stereoselectively biocatalytic carboligation reactions is presented. First, the benzoin reaction of aromatic aldehydes to dimethoxyacetaldehyde is conducted, catalyzed by benzaldehyde lyase from Pseudomonas fluorescens biovar I. Then, the α-hydroxyketones formed are reduced by using NaBH4 yielding the anti diol. After acetal hydrolysis, the aldol addition of dihydroxyacetone, hydroxyacetone, or glycolaldehyde catalyzed by the stereocomplementary D-fructose-6-phosphate aldolase and L-rhamnulose-1-phosphate aldolase is performed. Both aldolases accept unphosphorylated donor substrates, avoiding the need of handling the phosphate group that the dihydroxyacetone phosphate-dependent aldolases require. In this way, 6-C-aryl-L-sorbose, 6-C-aryl-L-fructose, 6-C-aryl-L-tagatose, and 5-C-aryl-L-xylose derivatives are prepared by using this methodology.<br /> (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Subjects :
- Aldehyde-Lyases metabolism
Biocatalysis
Carbohydrates chemistry
Escherichia coli metabolism
Fructosephosphates chemistry
Molecular Structure
Aldehyde-Lyases chemistry
Aldehydes chemistry
Benzoin chemistry
Carbohydrates chemical synthesis
Dihydroxyacetone chemistry
Escherichia coli chemistry
Fructosephosphates chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 21
- Issue :
- 8
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 25640727
- Full Text :
- https://doi.org/10.1002/chem.201406156