Chemo-enzymatic synthesis and glycosidase inhibitory properties of DAB and LAB derivatives.

@article{Concia2013ChemoenzymaticSA,
  title={Chemo-enzymatic synthesis and glycosidase inhibitory properties of DAB and LAB derivatives.},
  author={Alda Lisa Concia and L. G{\'o}mez and J. Bujons and T. Parella and C. Vilaplana and P. Cardona and J. Joglar and P. Clap{\'e}s},
  journal={Organic \& biomolecular chemistry},
  year={2013},
  volume={11 12},
  pages={
          2005-21
        }
}
A chemo-enzymatic strategy for the preparation of 2-aminomethyl derivatives of (2R,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol (also called 1,4-dideoxy-1,4-imino-D-arabinitol, DAB) and its enantiomer LAB is presented. The synthesis is based on the enzymatic preparation of DAB and LAB followed by the chemical modification of their hydroxymethyl functionality to afford diverse 2-aminomethyl derivatives. This strategy leads to novel aromatic, aminoalcohol and 2-oxopiperazine DAB and LAB… Expand
Inhibitory properties of 1,4-dideoxy-1,4-imino-d-arabinitol (DAB) derivatives acting on glycogen metabolising enzymes.
TLDR
Results are consistent with a model in which these compounds bind to the subsite in the active centre of the enzymes that is normally occupied by the glucosyl residue which is transferred between donor and acceptor substrates. Expand
A common strategy towards the synthesis of 1,4-dideoxy-1,4-imino-l-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars.
TLDR
A strategy towards the synthesis of three different target molecules, namely 1,4-dideoxy-1, 4-imino-l-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars, is reported from a common amino-vicinal diol intermediate derived from tri-O-benzyl-d-glucal. Expand
Casuarine stereoisomers from achiral substrates: chemoenzymatic synthesis and inhibitory properties.
TLDR
The new ent-3-epi-casuarine is a strong inhibitor of α-d-glucosidase from rice and of rat intestinal sucrase and its enantiomer DAB and LAB were obtained from dihydroxyacetone and aminoethanol using D-fructose-6-phosphate aldolase and L-rhamnulose-1-ph phosphate a Aldolase catalysts, respectively. Expand
Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.
TLDR
A library of sp(2)-iminosugar conjugates derived from the piperidine iminosugar d-fagomine and the enantiomeric pyrrolidine iminougars DAB and LAB is generated, showing an unfavourable chaperone/inhibitor balance on disease-associated GCase mutants in cellulo. Expand
Expedient synthesis of C-aryl carbohydrates by consecutive biocatalytic benzoin and aldol reactions.
TLDR
An expedient asymmetric "de novo" synthetic route to new aryl carbohydrate derivatives based on two sequential stereoselectively biocatalytic carboligation reactions is presented. Expand
Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.
TLDR
These new mimics of l-rhamnose may affect other enzymes associated with the biochemistry of rhamnosed including enzymes involved in progression of tuberculosis. Expand
C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat.
TLDR
L-IsoDMDP, prepared in 11 steps in an overall yield of 45% from d-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. Expand
l-Rhamnulose-1-phosphate and l-fuculose-1-phosphate aldolase mediated multi-enzyme cascade systems for nitrocyclitol synthesis
Abstract One-pot multistep stereoselective cascade reactions were implemented for the straightforward synthesis of various nitrocyclitols. Two kinases, an aldolase and a phosphatase were involved inExpand
Recent Developments in the Preparation of Carbohydrate Derivatives from Achiral Building Blocks by using Aldolases
The central role of carbohydrates in medicinal chemistry has stimulated intensive research in the last few years to develop simpler and more efficient routes for their preparation. Among them, routesExpand
Fructose-6-phosphate aldolases as versatile biocatalysts for nitrocyclitol syntheses
Efficient and stereoselective polyhydroxylated nitrocyclitol syntheses were performed via biocatalysed aldol reactions. The key step was based on a one-pot/one-enzyme cascade reaction process whereExpand
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Several 2-(aminomethyl)-and 2-(2-aminoethyl)-pyrrolidine-3,4-diol derivatives have been assayed for their inhibitory activities towards glycosidases. Good inhibitors of alpha-mannosidases must haveExpand
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Salacinol showed a much more potent inhibitory activity toward maltase in Caco-2 cell model system than its de-sulfonated derivative, and was further a stronger inhibitor of human lysosomal alpha-glucosidase than the derivative, which indicates that the sulfate in the side chain plays an important role in the specificity of enzyme inhibition. Expand
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