Synthesis of alkyl-alpha-L-rhamnosides by water soluble alcohols enzymatic glycosylation.
The synthesis of alkyl-alpha-rhamnosides by alpha-rhamnosidase was studied using rhamnose and rhamnosides, particularly the flavonoid naringin, as glycosylation agents, and water soluble alcohols as acceptors. The reaction products were analyzed by HPLC chromatography and identified by 13C y 1H NMR. The glycosylation of alcohols by reverse hydrolysis was maximum for 40% methanol, 30% ethanol, 10% propanol and 20% isopropanol. Under optimum conditions the yield of rhamnose to alkyl-alpha-rhamnoside transformation decreased from 68% for methyl-alpha-rhamnoside to 10% for isopropyl-alpha-rhamnoside. The time course of rhamnosylations produced using naringin as the donor was comparable with that of the reverse hydrolysis obtained at the same molar concentration of the donor. The flavonoids and their derivatives remaining in the solution after the glycosylation were removed by ion exchange QEAE chromatography at pH 10. These results indicate that both, reverse hydrolysis and glycosylation by naringin are acceptable procedures for the enzymatic synthesis of short chain length alkyl-alpha-L-rhamnosides.
Instituto de Investigaciones para la Industria Qui;mica (INIQUI), Universidad Nacional de Salta, Buenos Aires 177, 4400, Salta, Argentina.
M R
MR
Martearena
S
S
Blanco
G
G
Ellenrieder
D000438:Alcohols / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D002852:Chromatography, Ion Exchange; D044950:Flavanones / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000737:chemistry*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D012210:Rhamnose / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000438:Alcohols; D044950:Flavanones; D006026:Glycoside Hydrolases; C022525:alpha-L-rhamnosidase; C005274:naringin; D012210:Rhamnose