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

In connection with prospective (18)F-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, starti...

Descripción completa

Detalles Bibliográficos
Autores principales: Caputi, Lorenzo, Rejzek, Martin, Louveau, Thomas, O’Neill, Ellis C., Hill, Lionel, Osbourn, Anne, Field, Robert A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier Science 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3898844/
https://www.ncbi.nlm.nih.gov/pubmed/23806835
http://dx.doi.org/10.1016/j.bmc.2013.05.057
_version_ 1782300479594692608
author Caputi, Lorenzo
Rejzek, Martin
Louveau, Thomas
O’Neill, Ellis C.
Hill, Lionel
Osbourn, Anne
Field, Robert A.
author_facet Caputi, Lorenzo
Rejzek, Martin
Louveau, Thomas
O’Neill, Ellis C.
Hill, Lionel
Osbourn, Anne
Field, Robert A.
author_sort Caputi, Lorenzo
collection PubMed
description In connection with prospective (18)F-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.
format Online
Article
Text
id pubmed-3898844
institution National Center for Biotechnology Information
language English
publishDate 2013
publisher Elsevier Science
record_format MEDLINE/PubMed
spelling pubmed-38988442014-01-24 A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate() Caputi, Lorenzo Rejzek, Martin Louveau, Thomas O’Neill, Ellis C. Hill, Lionel Osbourn, Anne Field, Robert A. Bioorg Med Chem Article In connection with prospective (18)F-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. Elsevier Science 2013-08-15 /pmc/articles/PMC3898844/ /pubmed/23806835 http://dx.doi.org/10.1016/j.bmc.2013.05.057 Text en © 2013 The Authors https://creativecommons.org/licenses/by/3.0/This is an open access article under the CC BY license (https://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Caputi, Lorenzo
Rejzek, Martin
Louveau, Thomas
O’Neill, Ellis C.
Hill, Lionel
Osbourn, Anne
Field, Robert A.
A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate()
title A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate()
title_full A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate()
title_fullStr A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate()
title_full_unstemmed A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate()
title_short A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate()
title_sort one-pot enzymatic approach to the o-fluoroglucoside of n-methylanthranilate()
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3898844/
https://www.ncbi.nlm.nih.gov/pubmed/23806835
http://dx.doi.org/10.1016/j.bmc.2013.05.057
work_keys_str_mv AT caputilorenzo aonepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT rejzekmartin aonepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT louveauthomas aonepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT oneillellisc aonepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT hilllionel aonepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT osbournanne aonepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT fieldroberta aonepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT caputilorenzo onepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT rejzekmartin onepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT louveauthomas onepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT oneillellisc onepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT hilllionel onepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT osbournanne onepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate
AT fieldroberta onepotenzymaticapproachtotheofluoroglucosideofnmethylanthranilate

Ejemplares similares