82928-12-9

Upstream product

• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 50-99-7 D-glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 84534-36-1 (3R/3S)-linalyl β-D-D-glucopyranoside tetraacetate 
• 84534-33-8 (R,S)-linalyl 6-O-α-L-rhamnopyranosyl-β-D-glucopyranoside 
• 84543-11-3 (R,S)-linalyl-6-O-α-L-arabinofuranosyl-β-D-glucopyranoside 

Downstream Products

• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 50-99-7 D-glucose 

Relevant academic research and scientific papers

Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds

The synthesis of terpenoid glycosides typically uses a chemical strategy since few biocatalysts have been identified that recognise these scaffolds. In this study, a platform of 107 recombinant glycosyltransferases (GTs), comprising the multigene family of small molecule GTs of Arabidopsis thaliana have been screened against a range of model terpenoid acceptors to identify those enzymes with high activity. Twenty-seven GTs are shown to glycosylate a diversity of mono-, sesquiand diterpenes, such as geraniol, perillyl alcohol, artemisinic acid and retinoic acid. Certain enzymes showing substantial sequence similarity recognise terpenoids containing a primary alcohol, irrespective of the linear or cyclical structure of the scaffold; other GTs glycosylate scaffolds containing secondary and tertiary alcohols; the carboxyl group of other terpenoids also represents a feature that is recognized by GTs previously known to form glucose esters with many different compounds. These data underpin the rapid prediction of potential biocatalysts from GT sequence information. To explore the potential of GTs as biocatalysts, their use for the production of terpenoid glycosides was investigated by using a microbial-based whole-cell biotransformation system capable of regenerating the cofactor, UDP-glucose. A high cell density fermentation system was shown to produce several hundred milligrams of a model terpenoid, geranyl-glucoside. The activities of the GTs are discussed in relation to their substrate recognition and their utility in biotransformations as a complement or alternative to chemical synthesis.

Preparation of New Terpenyl β-D-Glucopyranosides by a Modified Koenigs-Knorr Procedure.

Ten new hemi- and monoterpenyl β-D-glucopyranosides have been prepared by a modification of the Koenigs-Knorr procedure which utilises silver fluoroacetate as a soluble catalyst coupled with the introduction of a basic ion-exchange resin to effect the deacetylation step.Most of these compounds could not be obtained in acceptable yields using the classical procedure.

SEQUENTIAL ENZYMIC HYDROLYSIS OF POTENTIALLY AROMATIC GLYCOSIDES FROM GRAPE

The mechanism of action of α-L-arabinofuranosidase, α-L-rhamnopyranosidase, and β-D-glucopyranosidase on p-nitrophenyl and grape monoterpenyl disaccharide-glycosides has been studied.First, the (1->6) linkage is cleaved by either α-L-arabinofuranosidase or α-L-rhamnosidase, and arabinose, rhamnose, and the corresponding monoterpenyl β-D-glucosides are released.Subsequently, liberation of monoterpenol takes place after action of β-D-glucosidase.The possible use of these glycosidases for the enhancement of the aroma of grape juice and derived beverages is emphasised.