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Rigid‐Rod β‐Barrel Ion Channels with Internal “Cascade Blue” Cofactors − Catalysis of Amide, Carbonate, and Ester Hydrolysis
Author(s) -
Som Abhigyan,
Matile Stefan
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200211)2002:22<3874::aid-ejoc3874>3.0.co;2-6
Subject(s) - chemistry , amide , chemoselectivity , hydrolysis , catalysis , benzaldehyde , carbonate , substrate (aquarium) , cofactor , combinatorial chemistry , organic chemistry , enzyme , oceanography , geology
The pyrene‐1,3,6‐trisulfonate scaffold is introduced as an internal cofactor for histidine‐rich p ‐octiphenyl β‐barrels with catalytic and ion channel activity to mediate binding and conversion of otherwise inaccessible benzaldehyde substrates. Up to 170,000‐fold accelerations of amide, ester, and carbonate hydrolysis, high substrate diversity, high chemoselectivity, and absence of enantioselectivity are reported. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)