Three important amino acids control the regioselectivity of flavonoid glucosidation in glycosyltransferase-1 from Bacillus cereus
Glycosyltransferase-1 from Bacillus cereus ( Bc GT1) catalyzes a reaction that transfers a glucosyl moiety to flavonoids, such as quercetin, kaempferol, and myricetin. The enzymatic glucosidation shows a broad substrate specificity when the reaction is catalyzed by wild-type Bc GT1. Preliminary assa...
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Published in | Applied microbiology and biotechnology Vol. 100; no. 19; pp. 8411 - 8424 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
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Springer Berlin Heidelberg
01.10.2016
Springer Springer Nature B.V |
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Abstract | Glycosyltransferase-1 from
Bacillus cereus
(
Bc
GT1) catalyzes a reaction that transfers a glucosyl moiety to flavonoids, such as quercetin, kaempferol, and myricetin. The enzymatic glucosidation shows a broad substrate specificity when the reaction is catalyzed by wild-type
Bc
GT1. Preliminary assays demonstrated that the F240A mutant significantly improves the regioselectivity of enzymatic glucosidation toward quercetin. To unveil and further to control the catalytic function of
Bc
GT1, mutation of F240 to other amino acids, such as C, E, G, R, Y, W, and K, was performed. Among these mutants, F240A, F240G, F240R, and F240K greatly altered the regioselectivity. The quercetin-3-
O
-glucoside, instead of quercetin-7-
O
-glucoside as for the wild-type enzyme, was obtained as the major product. Among these mutants, F240R showed nearly 100 % product specificity but only retained 25 % catalytic efficiency of wild-type enzyme. From an inspection of the protein structure, we found two other amino acids, F132 and F138, together with F240, are likely to form a hydrophobic binding region, which is sufficiently spacious to accommodate substrates with varied aromatic moieties. Through the replacement of a phenylalanine by a tyrosine residue in the substrate-binding region, the mutants may be able to fix the orientation of flavonoids, presumably through the formation of a hydrogen bond between substrates and mutants. Multiple mutants—F240R_F132Y, F240R_F138Y, and F240R_F132Y_F138Y—were thus constructed for further investigation. The multiple points of mutants not only maintained the high product specificity but also significantly improved the catalytic efficiency, relative to F240R. The same product specificity was obtained when kaempferol and myricetin were used as a substrate. |
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AbstractList | Glycosyltransferase-1 from Bacillus cereus (BcGT1) catalyzes a reaction that transfers a glucosyl moiety to flavonoids, such as quercetin, kaempferol, and myricetin. The enzymatic glucosidation shows a broad substrate specificity when the reaction is catalyzed by wild-type BcGT1. Preliminary assays demonstrated that the F240A mutant significantly improves the regioselectivity of enzymatic glucosidation toward quercetin. To unveil and further to control the catalytic function of BcGT1, mutation of F240 to other amino acids, such as C, E, G, R, Y, W, and K, was performed. Among these mutants, F240A, F240G, F240R, and F240K greatly altered the regioselectivity. The quercetin-3-O-glucoside, instead of quercetin-7-O-glucoside as for the wild-type enzyme, was obtained as the major product. Among these mutants, F240R showed nearly 100 % product specificity but only retained 25 % catalytic efficiency of wild-type enzyme. From an inspection of the protein structure, we found two other amino acids, F132 and F138, together with F240, are likely to form a hydrophobic binding region, which is sufficiently spacious to accommodate substrates with varied aromatic moieties. Through the replacement of a phenylalanine by a tyrosine residue in the substrate-binding region, the mutants may be able to fix the orientation of flavonoids, presumably through the formation of a hydrogen bond between substrates and mutants. Multiple mutants--F240R_F132Y, F240R_F138Y, and F240R_F132Y_F138Y--were thus constructed for further investigation. The multiple points of mutants not only maintained the high product specificity but also significantly improved the catalytic efficiency, relative to F240R. The same product specificity was obtained when kaempferol and myricetin were used as a substrate. Glycosyltransferase-1 from Bacillus cereus (BcGT1) catalyzes a reaction that transfers a glucosyl moiety to flavonoids, such as quercetin, kaempferol, and myricetin. The enzymatic glucosidation shows a broad substrate specificity when the reaction is catalyzed by wild-type BcGT1. Preliminary assays demonstrated that the F240A mutant significantly improves the regioselectivity of enzymatic glucosidation toward quercetin. To unveil and further to control the catalytic function of BcGT1, mutation of F240 to other amino acids, such as C, E, G, R, Y, W, and K, was performed. Among these mutants, F240A, F240G, F240R, and F240K greatly altered the regioselectivity. The quercetin-3-O-glucoside, instead of quercetin-7-O-glucoside as for the wild-type enzyme, was obtained as the major product. Among these mutants, F240R showed nearly 100 % product specificity but only retained 25 % catalytic efficiency of wild-type enzyme. From an inspection of the protein structure, we found two other amino acids, F132 and F138, together with F240, are likely to form a hydrophobic binding region, which is sufficiently spacious to accommodate substrates with varied aromatic moieties. Through the replacement of a phenylalanine by a tyrosine residue in the substrate-binding region, the mutants may be able to fix the orientation of flavonoids, presumably through the formation of a hydrogen bond between substrates and mutants. Multiple mutants-F240R_F132Y, F240R_F138Y, and F240R_F132Y_F138Y-were thus constructed for further investigation. The multiple points of mutants not only maintained the high product specificity but also significantly improved the catalytic efficiency, relative to F240R. The same product specificity was obtained when kaempferol and myricetin were used as a substrate. Glycosyltransferase-1 from Bacillus cereus ( Bc GT1) catalyzes a reaction that transfers a glucosyl moiety to flavonoids, such as quercetin, kaempferol, and myricetin. The enzymatic glucosidation shows a broad substrate specificity when the reaction is catalyzed by wild-type Bc GT1. Preliminary assays demonstrated that the F240A mutant significantly improves the regioselectivity of enzymatic glucosidation toward quercetin. To unveil and further to control the catalytic function of Bc GT1, mutation of F240 to other amino acids, such as C, E, G, R, Y, W, and K, was performed. Among these mutants, F240A, F240G, F240R, and F240K greatly altered the regioselectivity. The quercetin-3- O -glucoside, instead of quercetin-7- O -glucoside as for the wild-type enzyme, was obtained as the major product. Among these mutants, F240R showed nearly 100 % product specificity but only retained 25 % catalytic efficiency of wild-type enzyme. From an inspection of the protein structure, we found two other amino acids, F132 and F138, together with F240, are likely to form a hydrophobic binding region, which is sufficiently spacious to accommodate substrates with varied aromatic moieties. Through the replacement of a phenylalanine by a tyrosine residue in the substrate-binding region, the mutants may be able to fix the orientation of flavonoids, presumably through the formation of a hydrogen bond between substrates and mutants. Multiple mutants—F240R_F132Y, F240R_F138Y, and F240R_F132Y_F138Y—were thus constructed for further investigation. The multiple points of mutants not only maintained the high product specificity but also significantly improved the catalytic efficiency, relative to F240R. The same product specificity was obtained when kaempferol and myricetin were used as a substrate. |
Audience | Academic |
Author | Chiu, Hsi-Ho Chen, Ya-Huei Hsieh, Yin-Cheng Lu, Chia-Yu Wang, Hsin-Ying Chen, Chun-Jung Li, Yaw-Kuen |
Author_xml | – sequence: 1 givenname: Hsi-Ho surname: Chiu fullname: Chiu, Hsi-Ho organization: Department of Applied Chemistry, National Chiao Tung University – sequence: 2 givenname: Yin-Cheng surname: Hsieh fullname: Hsieh, Yin-Cheng organization: Life Science Group, Scientific Research Division, National Synchrotron Radiation Research Center – sequence: 3 givenname: Ya-Huei surname: Chen fullname: Chen, Ya-Huei organization: Department of Applied Chemistry, National Chiao Tung University – sequence: 4 givenname: Hsin-Ying surname: Wang fullname: Wang, Hsin-Ying organization: Degree Program of Applied Science and Technology, College of Science, National Chiao Tung University – sequence: 5 givenname: Chia-Yu surname: Lu fullname: Lu, Chia-Yu organization: Department of Applied Chemistry, National Chiao Tung University – sequence: 6 givenname: Chun-Jung surname: Chen fullname: Chen, Chun-Jung email: cjchen@nsrrc.org.tw organization: Life Science Group, Scientific Research Division, National Synchrotron Radiation Research Center – sequence: 7 givenname: Yaw-Kuen surname: Li fullname: Li, Yaw-Kuen email: ykl@faculty.nctu.edu.tw organization: Department of Applied Chemistry, National Chiao Tung University |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27198725$$D View this record in MEDLINE/PubMed |
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CitedBy_id | crossref_primary_10_1007_s13205_021_02855_z crossref_primary_10_1016_j_ijbiomac_2024_130229 crossref_primary_10_1002_pld3_372 crossref_primary_10_1021_acs_jafc_1c02518 crossref_primary_10_1007_s00253_020_10895_3 crossref_primary_10_1038_s42003_023_05150_0 crossref_primary_10_1016_j_ijbiomac_2024_133205 crossref_primary_10_3390_antibiotics11101380 crossref_primary_10_1021_acs_jafc_7b03907 crossref_primary_10_3390_nu13082688 crossref_primary_10_1093_glycob_cwz056 |
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Keywords | Glucosidation Regioselectivity GT1 Flavonoid Glucosyltransferase BcGT1 |
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Snippet | Glycosyltransferase-1 from
Bacillus cereus
(
Bc
GT1) catalyzes a reaction that transfers a glucosyl moiety to flavonoids, such as quercetin, kaempferol, and... Glycosyltransferase-1 from Bacillus cereus (BcGT1) catalyzes a reaction that transfers a glucosyl moiety to flavonoids, such as quercetin, kaempferol, and... |
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SubjectTerms | Amino Acid Substitution Amino acids Amino Acids - genetics Amino Acids - metabolism Analysis Bacillus cereus Bacillus cereus - enzymology Bacteria Binding Sites Biomedical and Life Sciences Biotechnologically Relevant Enzymes and Proteins Biotechnology Catalysis Enzymes Flavonoids Flavonoids - metabolism Glucose Glycosylation Glycosyltransferases Glycosyltransferases - chemistry Glycosyltransferases - genetics Glycosyltransferases - metabolism Internet resources Life Sciences Microbial Genetics and Genomics Microbiology Mutagenesis, Site-Directed Mutant Proteins - genetics Mutant Proteins - metabolism Mutation Physiological aspects Plasmids Protein Conformation Proteins Science Sensors Solvents Studies Substrate Specificity |
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Title | Three important amino acids control the regioselectivity of flavonoid glucosidation in glycosyltransferase-1 from Bacillus cereus |
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