Chemoenzymatic Synthesis of Thiazolyl Peptide Natural Products Featuring an Enzyme-Catalyzed Formal [4 + 2] Cycloaddition
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چکیده
منابع مشابه
Computational Insights into an Enzyme-Catalyzed [4+2] Cycloaddition
The enzyme SpnF, involved in the biosynthesis of spinosyn A, catalyzes a formal [4+2] cycloaddition of a 22-membered macrolactone, which may proceed as a concerted [4+2] Diels-Alder reaction or a stepwise [6+4] cycloaddition followed by a Cope rearrangement. Quantum mechanics/molecular mechanics (QM/MM) calculations combined with free energy simulations show that the Diels-Alder pathway is favo...
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(-)-Gephyrotoxin-223 was formally synthesized from chiral synthon 1 which has been chemoenzymatically synthesized in the presence of Candida Antartica lipase.
متن کاملchemoenzymatic enantioselective formal synthesis of (-)-gephyrotoxin-223
(-)-gephyrotoxin-223 was formally synthesized from chiral synthon 1 which has been chemoenzymatically synthesized in the presence of candida antartica lipase.
متن کاملEnantioselective formal synthesis of (-)-englerin A via a Rh-catalyzed [4 + 3] cycloaddition reaction.
An enantioselective formal synthesis of (-)-englerin A (1) is reported. Key to the strategy is a Rh-catalyzed [4 + 3] cycloaddition reaction between furan 10 and diazo ester 11 that, following an intramolecular aldol condensation, produces the tricyclic scaffold of englerin. This strategy also provides a rapid, efficient, and stereoselective access to the biologically significant core motif of ...
متن کاملConcerted, highly asynchronous, enzyme-catalyzed [4 + 2] cycloaddition in the biosynthesis of spinosyn A; computational evidence.
A theoretical study has been carried out on model systems to study a recently reported, (Nature, 2011, 473, 109) biosynthetic, [4 + 2] cycloaddition catalyzed by a stand-alone enzyme (the cyclase SpnF). It was suggested in this paper that SpnF is the first known example of a Diels-Alderase (DA). In the present study, for a model system of the substrate a transition structure was found with dens...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2015
ISSN: 0002-7863,1520-5126
DOI: 10.1021/jacs.5b00940