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전병선
전병선 (Byung-sun Jeon) 저자 이메일 보기
University of Texas at Austin
 
조회 339  인쇄하기 주소복사 트위터 공유 페이스북 공유 
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Investigation of the mechanism of the SpnF-catalyzed [4+2]-cycloaddition reaction in the biosynthesis of spinosyn A
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Abstract
The Diels-Alder reaction is one of the most common methods to chemically synthesize a six-membered carbocycle. While it has long been speculated that the cyclohexene moiety found in many secondary metabolites is also introduced via similar chemistry, the enzyme SpnF involved in the biosynthesis of the insecticide spinosyn A in Saccharopolyspora spinosa is the first enzyme for which catalysis of an intramolecular [4+2]-cycloaddition has been experimentally verified as its only known function. Since its discovery, a number of additional standalone [4+2]-cyclases have been reported as potential Diels-Alderases; however, whether their catalytic cycles involve a concerted or stepwise cyclization mechanism has not been addressed experimentally. Here, we report direct experimental interrogation of the reaction coordinate for the [4+2]-carbocyclase SpnF via the measurement of α-secondary deuterium kinetic isotope effects (KIEs) at all sites of sp2→sp3 rehybridization for both the nonenzymatic and enzyme-catalyzed cyclization of the SpnF substrate. The measured KIEs for the nonenzymatic reaction are consistent with previous computational results implicating an intermediary state between formation of the first and second carbon-carbon bonds. The KIEs measured for the enzymatic reaction suggest a similar mechanism of cyclization within the enzyme active site; however, there is evidence that conformational restriction of the substrate may play a role in catalysis.

Diels-Alderase, isotope effect, enzyme, spinosyn, Bayesian analysis

논문정보
- 형식: Research article
- 게재일: 2017년 09월 (BRIC 등록일 2017-09-07)
- 연구진: 국외연구진
- 분야: Biochemistry
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Google (by Byung-sun Jeon)
Pubmed (by Byung-sun Jeon)
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[GE APAC Fast Trak] 다운스트림 바이오프로세스 개발과정 (DEV2)
[GE APAC Fast Trak] 다운스트림 바이오프로세스 개발과정 (DEV2)
사전접수: ~2017.10.13
날짜: 2017.10.16~20
장소: 인천시 연수구 송도미래로 9 BRC 2동 2층 GE Healthcare APAC Fast Trak Center
혁신적 진단 플랫폼 기술 개발 공모전
혁신적 진단 플랫폼 기술 개발 공모전
날짜: 2017.10.11
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