7196-71-6

Upstream product

• 133-89-1 UDP-glucose 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 830322-96-8 1,2,3,4,6-penta-O-chloroacetyl-α,β-D-glucopyranose 
• 30572-07-7 2,3,4,6-tetra-O-chloroacetyl-D-glucopyranose 
• 830322-97-9 2,3,4,6-tetra-O-chloroacetylglucosyl trichloroacetimidate 

Relevant academic research and scientific papers

Identification of UGT84A13 as a candidate enzyme for the first committed step of gallotannin biosynthesis in pedunculate oak (Quercus robur)

A cDNA encoding the ester-forming hydroxybenzoic acid glucosyltransferase UGT84A13 was isolated from a cDNA library of Quercus robur swelling buds and young leaves. The enzyme displayed high sequence identity to resveratrol/hydroxycinnamate and hydroxybenzoate/hydroxycinnamate glucosyltransferases from Vitis species and clustered to the phylogenetic group L of plant glucosyltransferases, mainly involved in the formation of 1-O-β-d-glucose esters. In silico transcriptome analysis confirmed expression of UGT84A13 in Quercus tissues which were previously shown to exhibit UDP-glucose:gallic acid glucosyltransferase activity. UGT84A13 was functionally expressed in Escherichia coli as N-terminal His-tagged protein. In vitro kinetic measurements with the purified recombinant enzyme revealed a clear preference for hydroxybenzoic acids as glucosyl acceptor in comparison to hydroxycinnamic acids. Of the preferred in vitro substrates, protocatechuic, vanillic and gallic acid, only the latter and its corresponding 1-O-?-D-glucose ester were found to be accumulated in young oak leaves. This indicates that in planta UGT84A13 catalyzes the formation of, 1-O-galloyl-?-D-glucose, the first committed step of gallotannin biosynthesis.

Stereoselective synthesis of 1-O-β-feruloyl and 1-O-β-sinapoyl glucopyranoses

1-O-β-Feruloyl and 1-O-β-sinapoyl glucopyranoses are two common substrates for serine carboxypeptidase-like acyltransferases and serve as acyl donors in the biosynthesis of numerous secondary metabolites. In addition, they are involved in plant cell wall

Biosynthesis of vanillin via ferulic acid in vanilla planifolia

14C-Labeled phenylalanine, 4-coumaric acid, 4- hydroxybenzaldehyde, 4-hydroxybenzyl alcohol, ferulic acid, and methionine were applied to disks of green vanilla pods 3 and 6 months after pollination (immature and mature pods), and the conversion of these compounds to vanillin or glucovanillin was investigated. In mature green vanilla pods, radioactivities of 11, 15, 29, and 24% from 14C-labeled phenylalanine, 4-coumaric acid, ferulic acid, and methionine, respectively, were incorporated into glucovanillin within 24 h. In the incorporation processes of methionine and phenylalanine into glucovanillin, some of the 14C labels were also trapped by the unlabeled ferulic acid. However, 14C-labeled 4-hydroxybenzaldehyde and 4-hydroxybenzyl alcohol were not converted to glucovanillin. On the other hand, in immature green vanilla pods radioactivities of the above six compounds were not incorporated into glucovanillin. Although 4-coumaric acid, ferulic acid, 4-hydroxybenzaldehyde, and 4-hydroxybenzyl alcohol were converted to the respective glucose esters or glucosides and vanillin was converted to glucovanillin, their conversions were believed to be from the detoxication of the aglycones. These results suggest that the biosynthetic pathway for vanillin is 4-coumaric acid → → ferulic acid → → vanillin → glucovanillin in mature vanilla pods.