Article | Published:

Using simple donors to drive the equilibria of glycosyltransferase-catalyzed reactions

Nature Chemical Biology volume 7, pages 685691 (2011) | Download Citation

Abstract

We report that simple glycoside donors can drastically shift the equilibria of glycosyltransferase-catalyzed reactions, transforming NDP-sugar formation from an endothermic to an exothermic process. To demonstrate the utility of this thermodynamic adaptability, we highlight the glycosyltransferase-catalyzed synthesis of 22 sugar nucleotides from simple aromatic sugar donors, as well as the corresponding in situ formation of sugar nucleotides as a driving force in the context of glycosyltransferase-catalyzed reactions for small-molecule glycodiversification. These simple aromatic donors also enabled a general colorimetric assay for glycosyltransfer, applicable to drug discovery, protein engineering and other fundamental sugar nucleotide–dependent investigations. This study directly challenges the general notion that NDP-sugars are 'high-energy' sugar donors when taken out of their traditional biological context.

  • Compound C16H18O8

    (4-Methylumbelliferone)-β-D-glucopyranoside

  • Compound C12H15NO8

    4-Nitrophenyl-β-D-glucopyranoside

  • Compound C12H15FO6

    2-Fluorophenyl-β-D-glucopyranoside

  • Compound C12H15ClO6

    2-Chlorophenyl-β-D-glucopyranoside

  • Compound C12H15BrO6

    2-Bromophenyl-β-D-glucopyranoside

  • Compound C12H15IO6

    2-Iodophenyl-β-D-glucopyranoside

  • Compound C12H15NO8

    2-Nitrophenyl-β-D-glucopyranoside

  • Compound C12H14FNO8

    2-Fluoro-4-nitrophenyl-β-D-glucopyranoside

  • Compound C12H14ClNO8

    2-Chloro-4-nitrophenyl-β-D-glucopyranoside

  • Compound C12H16O6

    Phenyl-β-D-glucopyranoside

  • Compound C12H15FO6

    4-Fluorophenyl-β-D-glucopyranoside

  • Compound C12H15ClO6

    4-Chlorophenyl-β-D-glucopyranoside

  • Compound C12H15BrO6

    4-Bromophenyl-β-D-glucopyranoside

  • Compound C12H16O5S

    S-Phenyl-1-thio-β-D-glucopyranoside

  • Compound C12H15NO7S

    S-(4-Nitrophenyl)-1-thio-β-D-glucopyranoside

  • Compound C12H17NO5

    N-Phenyl-β-D-glucopyranosylamine

  • Compound C12H16N2O7

    N-(4-Nitrophenyl)-β-D-glucopyranosylamine

  • Compound C12H16N2O7

    N-(3-Nitrophenyl)-β-D-glucopyranosylamine

  • Compound C12H16N2O7

    N-(2-Nitrophenyl)-D-glucopyranosylamine

  • Compound C12H15N3O9

    N-(3,5-Dinitrophenyl)-β-D-glucopyranosylamine

  • Compound C14H21NO6

    N-(N-Benzyl-N-methoxy)-β-D-glucopyranosylamine

  • Compound C15H23NO6

    N-(N-Benzyl-N-ethoxy)-β-D-glucopyranosylamine

  • Compound C20H25NO6

    N-(N-Benzoxy-N-benzyl)-β-D-glucopyranosylamine

  • Compound C18H23NO6

    N-(N-Methoxy-N-naphthalen-1-yl-methyl)-β-D-glucopyranosylamine

  • Compound C19H25NO6

    N-(N-Ethoxy-N-naphthalen-1-yl-methyl)-β-D-glucopyranosylamine

  • Compound C24H27NO6

    N-(N-Benzoxy-N-naphthalen-1-yl-methyl)-β-D-glucopyranosylamine

  • Compound C18H23NO6

    N-(N-Methoxy-N-naphthalen-2-yl-methyl)-β-D-glucopyranosylamine

  • Compound C19H25NO6

    N-(N-Ethoxy-N-naphthalen-2-yl-methyl)-β-D-glucopyranosylamine

  • Compound C24H27NO6

    N-(N-Benzoxy-N-naphthalen-2-yl-methyl)-β-D-glucopyranosylamine

  • Compound C20H25NO6

    N-(N-Benzhydryl-N-methoxy)-β-D-glucopyranosylamine

  • Compound C21H27NO6

    N-(N-Benzhydryl-N-ethoxy)-β-D-glucopyranosylamine

  • Compound C26H29NO6

    N-(N-Benzhydryl-N-benzoxy)-β-D-glucopyranosylamine

  • Compound C15H22N2O17P22-

    Uridine 5'-diphospo-α-D-glucopyranoside

  • Compound C16H24N2O16P22-

    Thymidine 5'-diphospo-α-D-glucopyranoside

  • Compound C12H13ClFNO7

    (2-Chloro-4-nitrophenyl)-6-deoxy-6-fluoro-β-D-glucopyranoside

  • Compound C12H13BrClNO7

    (2-Chloro-4-nitrophenyl)-6-bromo-6-deoxy-β-D-glucopyranose

  • Compound C12H14ClNO7S

    (2-Chloro-4-nitrophenyl)-6-deoxy-6-thio-β-D-glucopyranoside

  • Compound C12H13ClN4O7

    (2-Chloro-4-nitrophenyl)-6-azido-6-deoxy-β-D-glucopyranoside

  • Compound C11H12ClNO7

    2-Chloro-4-nitrophenyl-β-D-xylopyranoside

  • Compound C12H14ClNO7

    (2-Chloro-4-nitrophenyl)-2-deoxy-β-D-glucopyranoside

  • Compound C12H14ClNO7

    (2-Chloro-4-nitrophenyl)-3-deoxy-β-D-glucopyranoside

  • Compound C12H14ClNO7

    (2-Chloro-4-nitrophenyl)-4-deoxy-β-D-glucopyranoside

  • Compound C12H14ClNO7

    (2-Chloro-4-nitrophenyl)-6-deoxy-β-D-glucopyranoside

  • Compound C12H14ClNO8

    2-Chloro-4-nitrophenyl-β-D-mannopyranoside

  • Compound C12H14ClNO8

    2-Chloro-4-nitrophenyl-β-D-allopyranoside

  • Compound C12H14ClNO8

    2-Chloro-4-nitrophenyl-β-D-galactopyranoside

  • Compound C12H14ClNO8

    2-Chloro-4-nitrophenyl-β-L-glucopyranoside

  • Compound C12H14ClNO7

    2-Chloro-4-nitrophenyl-α-L-rhamnopyranoside

  • Compound C15H21FN2O16P22-

    Uridine 5'-diphospo-6-deoxy-6-fluoro-α-D-glucopyranoside

  • Compound C16H23FN2O15P22-

    Thymidine 5'-diphospo-6-deoxy-6-fluoro-α-D-glucopyranoside

  • Compound C15H21BrN2O16P22-

    Uridine 5'-diphospo-6-deoxy-6-bromo-α-D-glucopyranoside

  • Compound C16H23BrN2O15P22-

    Thymidine 5'-diphospo-6-deoxy-6-bromo-α-D-glucopyranoside

  • Compound C15H22N2O16P2S2-

    Uridine 5'-diphospo-6-deoxy-6-thio-α-D-glucopyranoside

  • Compound C16H24N2O15P2S2-

    Thymidine 5'-diphospo-6-deoxy-6-thio-α-D-glucopyranoside

  • Compound C15H21N5O16P22-

    Uridine 5'-diphospo-6-deoxy-6-azido-α-D-glucopyranoside

  • Compound C16H23N5O15P22-

    Thymidine 5'-diphospo-6-deoxy-6-azido-α-D-glucopyranoside

  • Compound C14H20N2O16P22-

    Uridine 5'-diphospo-α-D-xylopyranoside

  • Compound C15H22N2O15P22-

    Thymidine 5'-diphospo-α-D-xylopyranoside

  • Compound C15H22N2O16P22-

    Uridine 5'-diphospo-2-deoxy-α-D-glucopyranoside

  • Compound C16H24N2O15P22-

    Thymidine 5'-diphospo-2-deoxy-α-D-glucopyranoside

  • Compound C15H22N2O16P22-

    Uridine 5'-diphospo-3-deoxy-α-D-glucopyranoside

  • Compound C16H24N2O15P22-

    Thymidine 5'-diphospo-3-deoxy-α-D-glucopyranoside

  • Compound C15H22N2O16P22-

    Uridine 5'-diphospo-4-deoxy-α-D-glucopyranoside

  • Compound C16H24N2O15P22-

    Thymidine 5'-diphospo-4-deoxy-α-D-glucopyranoside

  • Compound C15H22N2O16P22-

    Uridine 5'-diphospo-6-deoxy-α-D-glucopyranoside

  • Compound C16H24N2O15P22-

    Thymidine 5'-diphospo-6-deoxy-α-D-glucopyranoside

  • Compound C15H22N2O17P22-

    Uridine 5'-diphospo-α-D-allopyranoside

  • Compound C16H24N2O16P22-

    Thymidine 5'-diphospo-α-D-allopyranoside

  • Compound C10H8O3

    4-Methylumbelliferone

  • Compound C16H17FO7

    (4-Methylumbelliferone)-6-deoxy-6-fluoro-β-D-glucopyranoside

  • Compound C16H17BrO7

    (4-Methylumbelliferone)-6-bromo-6-deoxy-β-D-glucopyranoside

  • Compound C16H18O7S

    (4-Methylumbelliferone)-6-deoxy-6-thio-β-D-glucopyranoside

  • Compound C16H17N3O7

    (4-Methylumbelliferone)-6-azido-6-deoxy-β-D-glucopyranoside

  • Compound C15H16O7

    (4-Methylumbelliferone)-β-D-xylopyranoside

  • Compound C16H18O7

    (4-Methylumbelliferone)-2-deoxy-β-D-glucopyranoside

  • Compound C16H18O7

    (4-Methylumbelliferone)-3-deoxy-β-D-glucopyranoside

  • Compound C16H18O7

    (4-Methylumbelliferone)-4-deoxy-β-D-glucopyranoside

  • Compound C16H18O7

    (4-Methylumbelliferone)-6-deoxy-β-D-glucopyranoside

  • Compound C16H18O8

    (4-Methylumbelliferone)-β-D-allopyranoside

  • Compound C53H52Cl2N8O17

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-3-(Carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C59H62Cl2N8O22

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-(β-D-Glucopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C59H61Cl2FN8O21

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-(6-Deoxy-6-fluoro-β-D-glucopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C59H61BrCl2N8O21

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-(6-Bromo-6-deoxy-β-D-glucopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C59H62Cl2N8O21S

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-(6-Deoxy-6-thio-β-D-glucopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C59H61Cl2N11O21

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-(6-Azido-6-deoxy-β-D-glucopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C58H60Cl2N8O21

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-(β-D-Xylopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C59H62Cl2N8O21

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-(2-Deoxy-β-D-glucopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C59H62Cl2N8O21

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-(3-Deoxy-β-D-glucopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C59H62Cl2N8O21

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-(4-Deoxy-β-D-glucopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C59H62Cl2N8O21

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-(6-Deoxy-β-D-glucopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C59H62Cl2N8O22

    (3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-(β-D-Allopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid

  • Compound C20H23FO10

    (2-Fluorophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

  • Compound C20H23ClO10

    (2-Chlorophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

  • Compound C20H23BrO10

    (2-Bromophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

  • Compound C20H23IO10

    (2-Iodophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

  • Compound C20H22FNO12

    (2-Fluoro-4-nitrophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

  • Compound C20H23FO10

    (4-Fluorophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

  • Compound C20H23ClO10

    (4-Chlorophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

  • Compound C20H23BrO10

    (4-Bromophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

  • Compound C20H23NO11S

    S-(4-Nitrophenyl)-1-thio-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

  • Compound C8H9NO

    Benzaldehyde-O-methyloxime

  • Compound C8H11NO

    N-Methoxybenzylamine

  • Compound C9H11NO

    Benzaldehyde-O-ethyloxime

  • Compound C9H13NO

    N-Ethoxybenzylamine

  • Compound C14H13NO

    Benzaldehyde-O-benzyloxime

  • Compound C14H15NO

    N-Benzoxybenzylamine

  • Compound C12H11NO

    1-Naphthaldehyde-O-methyloxime

  • Compound C12H13NO

    N-Methoxy-1-naphthalenemethanamine

  • Compound C13H13NO

    1-Naphthaldehyde-O-ethyloxime

  • Compound C13H15NO

    N-Ethoxy-1-naphthalenemethanamine

  • Compound C18H15NO

    1-Naphthaldehyde-O-benzyloxime

  • Compound C18H17NO

    N-Benzoxy-1-naphthalenemethanamine

  • Compound C12H11NO

    2-Naphthaldehyde-O-methyloxime

  • Compound C12H13NO

    N-Methoxy-2-naphthalenemethanamine

  • Compound C13H13NO

    2-Naphthaldehyde-O-ethyloxime

  • Compound C13H15NO

    N-Ethoxy-2-naphthalenemethanamine

  • Compound C18H15NO

    2-Naphthaldehyde-O-benzyloxime

  • Compound C18H17NO

    N-Benzoxy-2-naphthalenemethanamine

  • Compound C14H13NO

    Benzophenone-O-methyloxime

  • Compound C14H15NO

    N-Methoxybenzhydrylamine

  • Compound C15H15NO

    Benzophenone-O-ethyloxime

  • Compound C15H17NO

    N-Ethoxybenzhydrylamine

  • Compound C20H17NO

    Benzophenone-O-benzyloxime

  • Compound C20H19NO

    N-Benzoxybenzhydrylamine

  • Compound C20H22ClNO12

    (2-Chloro-4-nitrophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

  • Compound C14H19FO9

    1,2,3,4-Tetra-O-acetyl-6-deoxy-6-fluoro-β-D-glucopyranose

  • Compound C18H19ClFNO10

    (2-Chloro-4-nitrophenyl)-2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-β-D-glucopyranoside

  • Compound C18H19BrClNO10

    (2-Chloro-4-nitrophenyl)-2,3,4-tri-O-acetyl-6-bromo-6-deoxy-β-D-glucopyranose

  • Compound C12H16BrN3O7

    1-Bromo-2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranose

  • Compound C18H19ClN4O10

    (2-Chloro-4-nitrophenyl)-2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-D-glucopyranoside

  • Compound C35H28ClNO11S

    (2-Chloro-4-nitrophenyl)-2,3,4-tri-O-benzoyl-6-S-acetyl-6-deoxy-β-D-glucopyranoside

  • Compound C17H18ClNO10

    (2-Chloro-4-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-xylopyranoside

  • Compound C18H20ClNO10

    (2-Chloro-4-nitrophenyl)-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

  • Compound C18H20ClNO10

    (2-Chloro-4-nitrophenyl)-2,4,6-tri-O-acetyl-3-deoxy-β-D-glucopyranoside

  • Compound C33H26ClNO10

    (2-Chloro-4-nitrophenyl)-2,3,6-tri-O-benzoyl-4-deoxy-β-D-glucopyranoside

  • Compound C18H20ClNO10

    (2-Chloro-4-nitrophenyl)-2,3,4-tri-O-acetyl-6-deoxy-β-D-glucopyranoside

  • Compound C17H16ClNO11

    (2-Chloro-4-nitrophenyl)-4,6-di-O-acetyl-2,3-carbonyl-β-D-mannopyranoside

  • Compound C20H22ClNO12

    (2-Chloro-4-nitrophenyl)-2,3,4,6-tetra-O-acetyl-β-D-allopyranoside

  • Compound C20H22ClNO12

    (2-Chloro-4-nitrophenyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

  • Compound C20H22ClNO12

    (2-Chloro-4-nitrophenyl)-2,3,4,6-tetra-O-acetyl-β-L-glucopyranoside

  • Compound C18H20ClNO10

    2-Chloro-4-nitrophenyl-2,3,4-tri-O-acetyl-α-L-rhamnopyranose

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References

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    et al. (eds.). Essentials of Glycobiology 2nd edn. (Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York, USA, 2009).

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Acknowledgements

This manuscript is dedicated to the late C. Richard Hutchinson for his pioneering contributions to engineered natural product glycosylation. We thank the School of Pharmacy Analytical Instrumentation Center (University of Wisconsin–Madison) for analytical support and G.J. Williams (North Carolina State University) for materials and helpful discussion. R.W.G. is an American Foundation for Pharmaceutical Education Pre-Doctoral Fellow. J.S.T. is a University of Wisconsin H.I. Romnes Fellow and holds the Laura and Edward Kremers Chair in Natural Products. This work was supported by US National Institutes of Health grant AI52218.

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  1. Pharmaceutical Sciences Division, School of Pharmacy, Wisconsin Center for Natural Products Research, University of Wisconsin–Madison, Madison, Wisconsin, USA.

    • Richard W Gantt
    • , Pauline Peltier-Pain
    • , William J Cournoyer
    •  & Jon S Thorson

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Contributions

R.W.G., P.P.-P. and J.S.T. contributed to the experimental design. R.W.G., P.P.-P. and W.J.C. performed all experimental work. R.W.G., P.P.-P. and J.S.T. wrote and edited the manuscript.

Competing interests

J.S.T. is a co-founder of Centrose (Madison, Wisconsin, USA).

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Correspondence to Jon S Thorson.

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https://doi.org/10.1038/nchembio.638

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