Flavonoid glucosyltransferase

Offen W, Martinez-Fleites C, Yang M, Kiat-Lim E, Davis BG, Tarling CA, Ford CM, Bowles DJ, Davies GJ (2006) Structure of a flavonoid glucosyltransferase reveals the basis for plant natural product modification. EMBO J 25 1396-1405... 

Ogata J, Itoh Y, Ishida M, Yoshida Y, Ozeki Y (2004) Cloning and heterologous expression of cDNAs encoding flavonoid glucosyltransferases from Dianthus caryophyllus. Plant Biotechnol 21 367-375... 

Properties of the Glucosyltransferase. Except for its strict substrate specificity, the properties of this enzyme were similar to those of other flavonoid glucosyltransferases (32,33) and are listed in Table III. 

Yamazaki, M. et al.. Two flavonoid glucosyltransferases from Petunia hybridw. molecular cloning, biochemical properties and developmentally regulated expression. Plant Mol. Biol, 48, 401, 2002. 

Dooner, H., and Nelson, O. E., 1977, Controlling element-induced alterations in UDPglucose flavonoid glucosyltransferase, the enzyme specified by the bronze locus in maize, Proc. Natl. Acad. Sci. USA 74 5623-5627. 

Larson, R., and Coe, E. H., 1977, Gene-dependent flavonoid glucosyltransferase in maize, Biochem. Genet. 15 153-156. 

Phenylalanine ammonia lyase (PAL), the first enzyme of the biosynthetic sequence, and a flavonoid glucosyltransferase, the last enzyme, appear to be located in the lumen of the membranes. Cinnamate 4-hydroxy-lase is membrane embedded, while other enzyme activities appear to be weakly associated with the cytoplasmic phase of endoplasmic reticulum membranes (Hrazdina... 

LATCHINIAN, L KHOURI, H.E., IBRAHIM, R.K. Fast protein affinity chromatography of two flavonoid glucosyltransferases. J. Chromatogr., 1987, 388, 235-242. 

Vogt, T., Zimmermann, E., Grimm, R., Meyer, M. and Strack, D. (1997) Are the characteristics of betanidin glucosyltransferases from cell-suspension cultures of Dorotheanthus bellidiformis indicative of their phylogenetic relationship with flavonoid glucosyltransferases Planta, 203, 349-61. 

Werner SR, Morgan JA (2009) Expression of a Dianthus flavonoid glucosyltransferase in Saccharomyces cerevisiae for whole-cell biocatalysis. J Biotechnol 142 233-241. doi 10.1016/j.jbiotec.2009.05.008... 

Kramer CM, Prata RT, Willits MG et al (2003) Cloning and regiospecificity studies of two flavonoid glucosyltransferases from Allium cepa. Phytochemistry 64 1069-1076... 

Figure 5.4. Abbreviated scheme for biosynthesis of major flavonoid subclasses, showing the primary enzymes and substrates leading to different subclasses. Bold-faced, uppercase abbreviations refer to enzyme names, whereas substrate names are presented in lowercase letters. PAL, phenylalanine ammonia lyase C4H, cinnamate 4-hydroxylase 4CL, 4-coumarate CoA ligase CHS, chalcone synthase CHI, chalcone isomerase CHR, chalcone reductase IPS, isoflavone synthase F3H, flavonone 3-hydroxylase F3 H, flavonoid 3 -hydroxylase F3 5 H, flavonoid 3 5 -hydroxylase FNSI/II, flavone synthase DFR, dihydroflavonol 4-reductase FLS, flavonol synthase ANS, anthocyanidin synthase LAR, leucoanthocyanidin reductase ANR, anthocyanidin reductase UFGT, UDP-glucose flavonoid 3-O-glucosyltransferase. R3 = H or OH. R5 = H or OH. Glc = glucose. Please refer to text for more information.

CL, 4-coumarate CoA ligase CHS, chalcone synthase CHI, chalcone isomerase F3H, flavanone 3-hydroxylase DFR, dihydroflavonol 4-reductase ANS, anthocyanidin synthase FGT, flavonoid 3-O-glucosyltransferase. 

The R locus determines the presence (R) or absence (r) of anthocyanins in the seed coat. R is required (with i and T) to produce black seed [10]. However the identity of the gene product encoded by this locus has not been reported. Todd and Vodkin [25] have demonstrated that brown seed coats (r) contain proanthocyanidin (PAs) and black seed coats (R) contain anthocyanins in addition to PAs and suggested that R acts subsequent to the formation of leucoanthocyanidin but previous to the formation of anthocyanins. UDP-glucose flavonoid 3-0-glucosyltransferase (UF3GT) should be considered a candidate gene of the R locus but its identiflcation has not yet been reported. 

Kovinich N, Saleem A, Amason JT, MUd B (2010) Eunctional characterization of a UDP-glucose flavonoid 3-Q-glucosyltransferase from the seed coat of black soybean (Glycine max (L.) Merr). Phytochemistry 71 1253-1263... 

Ford CM, Boss PK, Hoj PB (1998) Cloning and characterization of Vitis vinifera UDP-glucose flavonoid 3-O-glucosyltransferase, a homologue of the enzyme encoded by the maize bronze-1 locus that may primarily serve to glucosylate anthocyanidins in vivo. 1 Biol Chem 273 9224-9233... 

From extensive analysis of recombinant proteins, and the crystal structure of A. thaliana protein, detailed reaction mechanisms have been proposed. The ANS reaction likely proceeds via stereospecific hydroxylation of the leucoanthocyanidin (flavan-3,4-cA-diol) at the C-3 to give a flavan-3,3,4-triol, which spontaneously 2,3-dehydrates and isomerizes to 2-flaven-3,4-diol, which then spontaneously isomerizes to a thermodynamically more stable anthocyanidin pseudobase, 3-flaven-2,3-diol (Figure 3.2). The formation of 3-flaven-2,3-diol via the 2-flaven-3,4-diol was previously hypothesized by Heller and Forkmann. The reaction sequence, and the subsequent formation of the anthocyanidin 3-D-glycoside, does not require activity of a separate dehydratase, which was once postulated. Recombinant ANS and uridine diphosphate (UDP)-glucose flavonoid 3-D-glucosyltransferase (F3GT, sometimes... 

Schwinn, K.E. et al.. Expression of an Antirrhinum majus UDP-glucose flavonoid-3-0-glucosyltransferase transgene alters flavonoid glycosylation and acylation in lisianthus (Eustoma grandiflorum Grise.). Plant ScL, 125, 53, 1997. 

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