Transglycosylation of neohesperidin dihydrochalcone by Bacillus stearothermophilus maltogenic amylase.
Neohesperidin dihydrochalcone (NHDC), a sweet compound derived from citrus fruits, was modified to a series of its oligosaccharides by transglycosylation activity of Bacillus stearothermophilus maltogenic amylase (BSMA). Maltotriose as a donor was reacted with NHDC as an acceptor to glycosylate for the purpose of increasing the solubility of NHDC. Maltosyl-NHDC was a major transglycosylation product among the several transfer products by TLC analysis. The structure of the major transglycosylation product was determined to be maltosyl-alpha-(1,6)-neohesperidin dihydrochalcone by MALDI-TOF/MS and (1)H and (13)C NMR. Maltosyl-NHDC was 700 times more soluble in water and 7 times less sweet than NHDC.
Cho
J S
JS
Department of Food Science & Technology and Research Center for New Bio-Materials in Agriculture, Seoul National University, Suwon 441-744, Korea.
Yoo
S S
SS
Cheong
T K
TK
Kim
M J
MJ
Kim
Y
Y
Park
K H
KH
D002599:Chalcone / Q000031:analogs & derivatives* / Q000378:metabolism; D047188:Chalcones; D001411:Geobacillus stearothermophilus / Q000201:enzymology*; D006026:Glycoside Hydrolases / Q000378:metabolism*; D006031:Glycosylation; D006569:Hesperidin / Q000031:analogs & derivatives* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D047188:Chalcones; C013613:neohesperidin dihydrochalcone; D002599:Chalcone; D006569:Hesperidin; D006026:Glycoside Hydrolases; C120909:glucan 1,4-alpha-maltohydrolase