20486-34-4Relevant academic research and scientific papers
Functional Characterization and Protein Engineering of a Triterpene 3-/6-/2′-O-Glycosyltransferase Reveal a Conserved Residue Critical for the Regiospecificity
Bao, Yang-Oujie,Gao, Bai-Han,Li, Fu-Dong,Qiao, Xue,Shi, Xiao-Meng,Su, Hui-Fei,Wang, Hai-Dong,Ye, Min,Yi, Yang,Zhang, Meng
supporting information, (2022/01/06)
Engineering the function of triterpene glucosyltransferases (GTs) is challenging due to the large size of the sugar acceptors. In this work, we identified a multifunctional glycosyltransferase AmGT8 catalyzing triterpene 3-/6-/2′-O-glycosylation from the medicinal plant Astragalus membranaceus. To engineer its regiospecificity, a small mutant library was built based on semi-rational design. Variants A394F, A394D, and T131V were found to catalyze specific 6-O, 3-O, and 2′-O glycosylation, respectively. The origin of regioselectivity of AmGT8 and its A394F variant was studied by molecular dynamics and hydrogen deuterium exchange mass spectrometry. Residue 394 is highly conserved as A/G and is critical for the regiospecificity of the C- and O-GTs TcCGT1 and GuGT10/14. Finally, astragalosides III and IV were synthesized by mutants A394F, T131V and P192E. This work reports biocatalysts for saponin synthesis and gives new insights into protein engineering of regioselectivity in plant GTs.
Exploring the aglycon promiscuity of a new glycosyltransferase from Pueraria lobata
Sun, Lili,Chen, Dawei,Chen, Ridao,Xie, Kebo,Liu, Jimei,Yang, Lin,Dai, Jungui
supporting information, p. 1518 - 1521 (2016/03/12)
Enzymatic glycosylation catalyzed by glycosyltransferases has great potential for creating bioactive glycosylated small-molecule compounds. Here, we highlight the aglycon promiscuity of a new glycosyltransferase (PlGT7) from Pueraria lobata. PlGT7 exhibited the capability to glycosylate 26 structurally diverse drug-like scaffolds and simple phenolics with UDP-glucose to form O-, S-, and N-glycosides. The reversibility of PlGT7 coupled with its substrate flexibility was also exploited to generate bioactive glucosides with simple sugar donor. These studies indicate the significant potential of an enzymatic approach to the glycosylation of bioactive natural and unnatural products in drug discovery.
Total synthesis of apigenin 7,4′-di-O-β-glucopyranoside, a component of blue flower pigment of Salvia patens, and seven chiral analogues
Oyama, Kin-Ichi,Kondo, Tadao
, p. 2025 - 2034 (2007/10/03)
We have succeeded in the first total synthesis of apigenin 7,4′-di-O-β-D-glucopyranoside (1a), a component of blue pigment, protodelphin, from naringenin (2). Glycosylation of 2 according to Koenigs-Knorr reaction provided a monoglucoside 4a in 80% yield, and this was followed by DDQ oxidation to give apigenin 7-O-glucoside (12a). Further glycosylation of 4′-OH of 12a with 2,3,4,6-tetra-O-acetyl-α-D- glucopyranosyl fluoride (5a) was achieved using a Lewis acid-and-base promotion system (BF3·Et2O, 2,6-di-tert-butyl-4- methylpyridine, and 1,1,3,3-tetramethylguanidine) in 70% yield, and subsequent deprotection produced 1a. Synthesis of three other chiral isomers of 1a, with replacement of D-glucose at 7 and/or 4′-OH by L-glucose (1b-d), and four chiral isomers of apigenin 7-O-β-glucosides (6a,b) and 4′-O-β- glucosides (7a,b) also proved possible.
Chiral molecular recognition on formation of a metalloanthocyanin: A supramolecular metal complex pigment from blue flowers of salvia patens
Kondo, Tadao,Oyama, Kin-Ichi,Yoshida, Kumi
, p. 894 - 897 (2007/10/03)
Most blue flower color is the result of a metalloanthocyanin, a stoichiometric self-assembled supramolecular pigment consisting of six molecules of an anthocyanin, six molecules of an anthocyanin, six molecules of flavone, and two metal atoms. We have iso
