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Cho JS, Yoo SS, Cheong TK, Kim MJ, Kim Y, Park KH
Transglycosylation of neohesperidin dihydrochalcone by Bacillus stearothermophilus maltogenic amylase
Journal of Agricultural and Food Chemistry 48(2) (2000)
152-154
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-4)-Subst
Subst = hesperetin dihydrochalcone = SMILES COc1ccc(CCC(=O)c2{2}c(O)c{4}c(O)c{6}c2O)c{53}c1O |
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Citrus
(NCBI TaxID 2706,
species name lookup)
Bacillus stearothermophilus
(later renamed to: Geobacillus stearothermophilus)
(NCBI TaxID 1422,
species name lookup)
Taxonomic group: plant, bacteria / Streptophyta, Firmicutes
(Phylum: Streptophyta, Firmicutes)
Organ / tissue: fruit
NCBI PubMed ID: 10691608Publication DOI: 10.1021/jf991044yJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: parkkh
plaza.snu.ac.kr
Institutions: Department of Food Science & Technology and Research Center for New Bio-Materials in Agriculture, Seoul National University, Suwon, South Korea
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-α-(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.
transglycosylation, Bacillus stearothermophilus maltogenic amylase (BSMA), neohesperidin dihydrochalcone (NHDC), maltosyl-α-(1, 6)-neohesperidin dihydrochalcone
Structure type: oligomer
Location inside paper: p. 153, Fig. 1, NHDC
Compound class: glycoside, chalcone glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, MALDI-TOF MS, GPC, UV, column chromatography, enzymatic assay, spectrophotometry, evaporation, centrifugation, taste analysis
Enzymes that release or process the structure: Bacillus stearothermophilus maltogenic amylase (BSMA)
Related record ID(s): 65145
NCBI Taxonomy refs (TaxIDs): 2706,
1422
Show glycosyltransferases
NMR conditions: in DMSO-d6 at 300(C) K
[as TSV]
13C NMR data: present in publication
|
There is only one chemically distinct structure:
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Cho JS, Yoo SS, Cheong TK, Kim MJ, Kim Y, Park KH
Transglycosylation of neohesperidin dihydrochalcone by Bacillus stearothermophilus maltogenic amylase
Journal of Agricultural and Food Chemistry 48(2) (2000)
152-154
|
a-L-Rhap-(1-2)-+
|
a-D-Glcp-(1-4)-a-D-Glcp-(1-6)-b-D-Glcp-(1-4)-Subst
Subst = hesperetin dihydrochalcone = SMILES COc1ccc(CCC(=O)c2{2}c(O)c{4}c(O)c{6}c2O)c{53}c1O |
Show graphically |
Citrus
(NCBI TaxID 2706,
species name lookup)
Bacillus stearothermophilus
(later renamed to: Geobacillus stearothermophilus)
(NCBI TaxID 1422,
species name lookup)
Taxonomic group: plant, bacteria / Streptophyta, Firmicutes
(Phylum: Streptophyta, Firmicutes)
Organ / tissue: fruit
NCBI PubMed ID: 10691608Publication DOI: 10.1021/jf991044yJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: parkkh
plaza.snu.ac.kr
Institutions: Department of Food Science & Technology and Research Center for New Bio-Materials in Agriculture, Seoul National University, Suwon, South Korea
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-α-(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.
transglycosylation, Bacillus stearothermophilus maltogenic amylase (BSMA), neohesperidin dihydrochalcone (NHDC), maltosyl-α-(1, 6)-neohesperidin dihydrochalcone
Structure type: oligomer ; 958.858 [M+Na]+
Location inside paper: p. 153, Fig. 1, G2-NHDC
Compound class: glycoside, chalcone glycoside
Contained glycoepitopes: IEDB_136105,IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, MALDI-TOF MS, GPC, UV, column chromatography, enzymatic assay, spectrophotometry, evaporation, centrifugation, taste analysis
Enzymes that release or process the structure: Bacillus stearothermophilus maltogenic amylase (BSMA)
Related record ID(s): 65144
NCBI Taxonomy refs (TaxIDs): 2706,
1422
Show glycosyltransferases
NMR conditions: in DMSO-d6 at 300(C) K
[as TSV]
13C NMR data: present in publication
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
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