Application of Racemization Process to Dynamic Resolution of ( RS )-Phenylephrine to ( R )-Phenylephrine β-D-Glucoside by Nicotiana tabacum Glucosyltransferase
Free accessResearch articleFirst published online November, 2018
Application of Racemization Process to Dynamic Resolution of ( RS )-Phenylephrine to ( R )-Phenylephrine β-D-Glucoside by Nicotiana tabacum Glucosyltransferase
Enzymatic glucosylation of racemic phenylephrine by glucosyltransferase from Nicotiana tabacum gave (R)-phenylephrine glucoside and recovered (S)-phenylephrine. [RuCl2(p-cymene)]2 complex associated with simple hemisalen ligands or zeolite were able to racemize (S)-phenylephrine. The [RuCl2(p-cymene)]2/Ligand/TEMPO or zeolite racemization was associated with the enantioselective glycosylation of racemic phenylephrine with glucosyltransferase. The (R)-stereoselective glucosylation of (RS)-phenylephrine occurred to produce a high yield of (R)-phenylephrine glucoside in high yield.
ShimodaK., KubotaN., HamadaM., UesugiD., TanigawaM., HamadaH., HamadaH. (2014) Glycosylation of quercetin with cultured plant cells and cyclodextrin glucanotransferase. Natural Product Communications, 9, 647–648.
2.
ShimodaK., KubotaN., UesugiD., HamadaH. (2014) Glycosylation of artepillin C with cultured plant cells of Phytolacca americana.Natural Product Communications, 9, 683–685.
3.
ShimodaK., KubotaN., UesugiD., FujitakaY., OkadaS., TanigawaM., HamadaH. (2015) Regioselective glycosylation of 3-, 5-, 6-, and 7- hydroxyflavones by cultured plant cellsNatural Product Communications, 10, 923–924.
4.
ShimodaK., KubotaN., HamadaH., HamadaH. (2015) Synthesis of resveratrol glycosides by plant glucosyltransferase and cyclodextrin glucanotransferase and their neuroprotective activity. Natural Product Communications, 10, 995–996
5.
HamadaH., HamadaH., ShimodaK. (2015) Synthesis of ε-viniferin glycosides by glucosyltransferase from Phytolacca americana and their inhibitory activity on histamine release from rat peritoneal mast cells. Natural Product Communications, 10, 1017–1018.
6.
ShimodaK., KubotaN., UesugiD., TanigawaM., HamadaH. (2016) Hydroxylation and glycosylation of phenylpropanoids by cultured cells of Phytolacca americana.Natural Product Communications, 11, 197–198.
7.
MatsumuraS., YamazakiH., ToshimaK. (1997) R-enantioselective galactosylation of secondary alcohols using β-galactosidase. Biotechnology Letters, 19, 583–586.
8.
LimE-K, DoucetC.J., HouB., JacksonR.G., AbramsS.R., BowlesD.J. (2005) Resolution of (+)-abscisic acid using an Arabidopsis glycosyltransferase. Tetrahedron: Assymmetry, 16, 143–147.
