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

Makoto N. Masuno | Zendy; Tadeusz F. Molinski | Zendy

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

Author(s) -

Makoto N. Masuno,

Tadeusz F. Molinski

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b01899

Subject(s) - catechol , chemistry , sulfatase , ether , chromatography , kinetic resolution , resolution (logic) , substrate (aquarium) , enzyme , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , oceanography , geology , artificial intelligence , computer science

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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