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Bifunctional Substr...
Bifunctional Substrate Activation via an Arginine Residue Drives Catalysis in Chalcone Isomerases
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- Burke, Jason R. (author)
- Salk Inst Biol Studies, Jack H Skirball Ctr Chem Biol & Prote, Howard Hughes Med Inst, 10010 N Torrey Pines Rd, La Jolla, CA 92037 USA;Calif State Univ San Bernardino, San Bernardino, CA 92407 USA
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- La Clair, James J. (author)
- Salk Inst Biol Studies, Jack H Skirball Ctr Chem Biol & Prote, Howard Hughes Med Inst, 10010 N Torrey Pines Rd, La Jolla, CA 92037 USA
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- Philippe, Ryan N. (author)
- Salk Inst Biol Studies, Jack H Skirball Ctr Chem Biol & Prote, Howard Hughes Med Inst, 10010 N Torrey Pines Rd, La Jolla, CA 92037 USA;Manus Biosynth, Cambridge, MA USA
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- Pabis, Anna (author)
- Uppsala universitet,Molekylär biofysik,Strukturbiologi
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- Corbella, Marina (author)
- Uppsala universitet,Institutionen för kemi - BMC
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- Jez, Joseph M. (author)
- Salk Inst Biol Studies, Jack H Skirball Ctr Chem Biol & Prote, Howard Hughes Med Inst, 10010 N Torrey Pines Rd, La Jolla, CA 92037 USA;Washington Univ, Dept Biol, Howard Hughes Med Inst, Campus Box 1137, St Louis, MO 63130 USA
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- Cortina, George A. (author)
- Univ Virginia, Dept Mol Physiol & Biomed Engn, Charlottesville, VA 22903 USA
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- Kaltenbach, Miriam (author)
- Weizmann Inst Sci, Dept Biomol Sci, IL-76100 Rehovot, Israel
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- Bowman, Marianne E. (author)
- Salk Inst Biol Studies, Jack H Skirball Ctr Chem Biol & Prote, Howard Hughes Med Inst, 10010 N Torrey Pines Rd, La Jolla, CA 92037 USA
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- Louie, Gordon V. (author)
- Salk Inst Biol Studies, Jack H Skirball Ctr Chem Biol & Prote, Howard Hughes Med Inst, 10010 N Torrey Pines Rd, La Jolla, CA 92037 USA
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- Woods, Katherine B. (author)
- Salk Inst Biol Studies, Jack H Skirball Ctr Chem Biol & Prote, Howard Hughes Med Inst, 10010 N Torrey Pines Rd, La Jolla, CA 92037 USA
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- Nelson, Andrew T. (author)
- Univ Texas Austin, Dept Chem, Austin, TX 78712 USA
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- Tawfik, Dan S. (author)
- Weizmann Inst Sci, Dept Biomol Sci, IL-76100 Rehovot, Israel
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- Kamerlin, Shina C. Lynn, 1981- (author)
- Uppsala universitet,Strukturbiologi,Biokemi
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- Noel, Joseph P. (author)
- Salk Inst Biol Studies, Jack H Skirball Ctr Chem Biol & Prote, Howard Hughes Med Inst, 10010 N Torrey Pines Rd, La Jolla, CA 92037 USA
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(creator_code:org_t)
- 2019-07-30
- 2019
- English.
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In: ACS Catalysis. - : AMER CHEMICAL SOC. - 2155-5435. ; 9:9, s. 8388-8396
- Related links:
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https://www.biorxiv....
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- Chalcone isomerases are plant enzymes that perform enantioselective oxa-Michael cyclizations of 2'-hydroxychalcones into flavanones. An X-ray crystal structure of an enzyme-product complex combined with molecular dynamics simulations reveal an enzyme mechanism wherein the guanidinium ion of a conserved arginine positions the nucleophilic phenoxide and activates the electrophilic enone for cyclization through Bronsted and Lewis acid interactions. The reaction terminates by asymmetric protonation of the carbanion intermediate syn to the guanidinium. Interestingly, bifunctional guanidine- and urea-based chemical reagents, increasingly used for asymmetric organocatalytic applications, share mechanistic similarities with this natural system. Comparative protein crystal structures and molecular dynamics simulations further demonstrate how two active site water molecules coordinate a hydrogen bond network that enables expanded substrate reactivity for 6'-deoxychalcones in more recently evolved type-2 chalcone isomerases.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
- NATURVETENSKAP -- Biologi -- Biokemi och molekylärbiologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences -- Biochemistry and Molecular Biology (hsv//eng)
Keyword
- Michaelase
- asymmetric biocatalysis
- arginine general acid
- catalytic water
- bifunctional guanidine catalysis
- enzyme evolution
- flavonoid biosynthesis
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Burke, Jason R.
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La Clair, James ...
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Philippe, Ryan N ...
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Pabis, Anna
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Corbella, Marina
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Jez, Joseph M.
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show more...
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Cortina, George ...
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Kaltenbach, Miri ...
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Bowman, Marianne ...
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Louie, Gordon V.
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Woods, Katherine ...
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Nelson, Andrew T ...
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Tawfik, Dan S.
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Kamerlin, Shina ...
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Noel, Joseph P.
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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and Organic Chemistr ...
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Biological Scien ...
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and Biochemistry and ...
- Articles in the publication
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ACS Catalysis
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Uppsala University