A Synergistic Combinatorial and Chiroptical Study of Peptide Catalysts for Asymmetric Baeyer-Villiger Oxidation

Autor:	Chung Yon Lin, Scott J. Miller, Eric V. Anslyn, Michael W. Giuliano, David K. Romney
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Circular dichroism Absolute configuration Peptide General Chemistry Monooxygenase Asymmetric induction Combinatorial chemistry Article Baeyer–Villiger oxidation Catalysis chemistry Organic chemistry Lactone
Zdroj:	Advanced Synthesis & Catalysis. 357:2301-2309
ISSN:	1615-4150
DOI:	10.1002/adsc.201500230
Popis:	We report an approach to the asymmetric Baeyer-Villiger oxidation utilizing bioinformatics-inspired combinatorial screening for catalyst discovery. Scaled-up validation of our on-bead efforts with a circular dichroism-based assay of alcohols derived from the products of solution-phase reactions established the absolute configuration of lactone products; this assay proved equivalent to HPLC in its ability to evaluate catalyst performance, but was far superior in its speed of analysis. Further solution-phase screening of a focused library suggested a mode of asymmetric induction that draws distinct parallels with the mechanism of Baeyer-Villiger monooxygenases.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::91856c05093bae62069880bf88c02011 https://doi.org/10.1002/adsc.201500230 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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