A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate.

L Caputi; M Rejzek; T Louveau; EC O'Neill; L Hill; A Osbourn; RA Field

doi:10.1016/j.bmc.2013.05.057

A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate.

L Caputi, M Rejzek, T Louveau, EC O'Neill, L Hill, A Osbourn, RA Field

Manchester Institute of Biotechnology

Research output: Contribution to journal › Article › peer-review

Abstract

In connection with prospective 18F-PET imaging studies, the potential for enzymatic synthesis of fluorine-labelled glycosides of small molecules was investigated. Approaches to the enzymatic synthesis of anomeric phosphates of d-gluco-configured fluorosugars proved ineffective. In contrast, starting in the d-galacto series and relying on the consecutive action of Escherichia coli galactokinase (GalK), galactose-1-phosphate uridylyltransferase (GalPUT), uridine-5′-diphosphogalactose 4-epimerase (GalE) and oat root glucosyltransferase (SAD10), a quick and effective synthesis of 6-deoxy-6-fluoro-d-glucosyl N-methylanthranilate ester was achieved.

Original language	Undefined
Pages (from-to)	4762-4767
Number of pages	6
Journal	Bioorg. Med. Chem.
Volume	21
DOIs	https://doi.org/10.1016/j.bmc.2013.05.057
Publication status	Published - Aug 2013

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Manchester Institute of Biotechnology

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title = "A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate.",

abstract = "In connection with prospective 18F-PET imaging studies, the potential for enzymatic synthesis of fluorine-labelled glycosides of small molecules was investigated. Approaches to the enzymatic synthesis of anomeric phosphates of d-gluco-configured fluorosugars proved ineffective. In contrast, starting in the d-galacto series and relying on the consecutive action of Escherichia coli galactokinase (GalK), galactose-1-phosphate uridylyltransferase (GalPUT), uridine-5′-diphosphogalactose 4-epimerase (GalE) and oat root glucosyltransferase (SAD10), a quick and effective synthesis of 6-deoxy-6-fluoro-d-glucosyl N-methylanthranilate ester was achieved.",

author = "L Caputi and M Rejzek and T Louveau and EC O'Neill and L Hill and A Osbourn and RA Field",

year = "2013",

month = aug,

doi = "10.1016/j.bmc.2013.05.057",

language = "Undefined",

volume = "21",

pages = "4762--4767",

journal = "Bioorg. Med. Chem.",

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T1 - A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate.

AU - Caputi, L

AU - Rejzek, M

AU - Louveau, T

AU - O'Neill, EC

AU - Hill, L

AU - Osbourn, A

AU - Field, RA

PY - 2013/8

Y1 - 2013/8

N2 - In connection with prospective 18F-PET imaging studies, the potential for enzymatic synthesis of fluorine-labelled glycosides of small molecules was investigated. Approaches to the enzymatic synthesis of anomeric phosphates of d-gluco-configured fluorosugars proved ineffective. In contrast, starting in the d-galacto series and relying on the consecutive action of Escherichia coli galactokinase (GalK), galactose-1-phosphate uridylyltransferase (GalPUT), uridine-5′-diphosphogalactose 4-epimerase (GalE) and oat root glucosyltransferase (SAD10), a quick and effective synthesis of 6-deoxy-6-fluoro-d-glucosyl N-methylanthranilate ester was achieved.

AB - In connection with prospective 18F-PET imaging studies, the potential for enzymatic synthesis of fluorine-labelled glycosides of small molecules was investigated. Approaches to the enzymatic synthesis of anomeric phosphates of d-gluco-configured fluorosugars proved ineffective. In contrast, starting in the d-galacto series and relying on the consecutive action of Escherichia coli galactokinase (GalK), galactose-1-phosphate uridylyltransferase (GalPUT), uridine-5′-diphosphogalactose 4-epimerase (GalE) and oat root glucosyltransferase (SAD10), a quick and effective synthesis of 6-deoxy-6-fluoro-d-glucosyl N-methylanthranilate ester was achieved.

UR - http://europepmc.org/abstract/med/23806835

U2 - 10.1016/j.bmc.2013.05.057

DO - 10.1016/j.bmc.2013.05.057

M3 - Article

C2 - 23806835

SN - 0968-0896

VL - 21

SP - 4762

EP - 4767

JO - Bioorg. Med. Chem.

JF - Bioorg. Med. Chem.

ER -

A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate.

Abstract

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