Resolution of Atropisomeric Cyclic Catechol Monoether O-Sulfate Esters by a Molluscan Sulfatase

[Image: see text] Atropisomeric cyclic catechol ethers are notoriously difficult to resolve by classical chiral phase high-performance liquid chromatography. Here, we show the first application of sulfatase enzymes for the kinetic resolution of O-sulfato-catechol ethers with enantioselectivities ran...

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Autores principales: Masuno, Makoto N., Molinski, Tadeusz F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6072249/
https://www.ncbi.nlm.nih.gov/pubmed/30087921
http://dx.doi.org/10.1021/acsomega.7b01899
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author Masuno, Makoto N.
Molinski, Tadeusz F.
author_facet Masuno, Makoto N.
Molinski, Tadeusz F.
author_sort Masuno, Makoto N.
collection PubMed
description [Image: see text] Atropisomeric cyclic catechol ethers are notoriously difficult to resolve by classical chiral phase high-performance liquid chromatography. Here, we show the first application of sulfatase enzymes for the kinetic resolution of O-sulfato-catechol ethers with enantioselectivities ranging from 30 to 65% ee, as determined by preparation of their Marfey’s ether derivatives. Substrate-structure dependence was briefly explored.
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spelling pubmed-60722492018-08-05 Resolution of Atropisomeric Cyclic Catechol Monoether O-Sulfate Esters by a Molluscan Sulfatase Masuno, Makoto N. Molinski, Tadeusz F. ACS Omega [Image: see text] Atropisomeric cyclic catechol ethers are notoriously difficult to resolve by classical chiral phase high-performance liquid chromatography. Here, we show the first application of sulfatase enzymes for the kinetic resolution of O-sulfato-catechol ethers with enantioselectivities ranging from 30 to 65% ee, as determined by preparation of their Marfey’s ether derivatives. Substrate-structure dependence was briefly explored. American Chemical Society 2018-07-12 /pmc/articles/PMC6072249/ /pubmed/30087921 http://dx.doi.org/10.1021/acsomega.7b01899 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Masuno, Makoto N.
Molinski, Tadeusz F.
Resolution of Atropisomeric Cyclic Catechol Monoether O-Sulfate Esters by a Molluscan Sulfatase
title Resolution of Atropisomeric Cyclic Catechol Monoether O-Sulfate Esters by a Molluscan Sulfatase
title_full Resolution of Atropisomeric Cyclic Catechol Monoether O-Sulfate Esters by a Molluscan Sulfatase
title_fullStr Resolution of Atropisomeric Cyclic Catechol Monoether O-Sulfate Esters by a Molluscan Sulfatase
title_full_unstemmed Resolution of Atropisomeric Cyclic Catechol Monoether O-Sulfate Esters by a Molluscan Sulfatase
title_short Resolution of Atropisomeric Cyclic Catechol Monoether O-Sulfate Esters by a Molluscan Sulfatase
title_sort resolution of atropisomeric cyclic catechol monoether o-sulfate esters by a molluscan sulfatase
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6072249/
https://www.ncbi.nlm.nih.gov/pubmed/30087921
http://dx.doi.org/10.1021/acsomega.7b01899
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