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

Lorenzo Caputi; Martin Rejzek; Thomas Louveau; Ellis C. O'Neill; Lionel Hill; Anne Osbourn; Robert A. Field

doi:10.1016/j.bmc.2013.05.057

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

Lorenzo Caputi, Martin Rejzek, Thomas Louveau, Ellis C. O'Neill, Lionel Hill, Anne Osbourn, Robert A. Field

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

8 Citations (Scopus)

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	English
Pages (from-to)	4762-4767
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	21
Issue number	16
DOIs	https://doi.org/10.1016/j.bmc.2013.05.057
Publication status	Published - 15 Aug 2013

Keywords

Biotransformation
Fluorosugar
Glucosyltransferase
Natural product
Sugar nucleotide

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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.",

keywords = "Biotransformation, Fluorosugar, Glucosyltransferase, Natural product, Sugar nucleotide",

author = "Lorenzo Caputi and Martin Rejzek and Thomas Louveau and O'Neill, {Ellis C.} and Lionel Hill and Anne Osbourn and Field, {Robert A.}",

note = "Funding Information: This work was supported by the UK BBSRC Institute Strategic Programme Grant on Understanding and Exploiting Metabolism (MET) [BB/J004561/1] and the John Innes Foundation .",

year = "2013",

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

language = "English",

volume = "21",

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journal = "Bioorganic & Medicinal Chemistry",

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

AU - Caputi, Lorenzo

AU - Rejzek, Martin

AU - Louveau, Thomas

AU - O'Neill, Ellis C.

AU - Hill, Lionel

AU - Osbourn, Anne

AU - Field, Robert A.

N1 - Funding Information: This work was supported by the UK BBSRC Institute Strategic Programme Grant on Understanding and Exploiting Metabolism (MET) [BB/J004561/1] and the John Innes Foundation .

PY - 2013/8/15

Y1 - 2013/8/15

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.

KW - Biotransformation

KW - Fluorosugar

KW - Glucosyltransferase

KW - Natural product

KW - Sugar nucleotide

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DO - 10.1016/j.bmc.2013.05.057

M3 - Article

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AN - SCOPUS:84880573817

VL - 21

SP - 4762

EP - 4767

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

SN - 0968-0896

IS - 16

ER -

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

Abstract

Keywords

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