气候变化领域集成服务门户(CCPortal): Total synthesis reveals atypical atropisomerism in a small-molecule natural product, tryptorubin A

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DOI	10.1126/science.aay9981
	Total synthesis reveals atypical atropisomerism in a small-molecule natural product, tryptorubin A
	Reisberg S.H.; Gao Y.; Walker A.S.; Helfrich E.J.N.; Clardy J.; Baran P.S.
发表日期	2020
ISSN	0036-8075
起始页码	458
结束页码	463
卷号	367 期号:6476
英文摘要	Molecular shape defines function in both biological and material settings, and chemists have developed an ever-increasing vernacular to describe these shapes. Noncanonical atropisomers—shape-defined molecules that are formally topologically trivial but are interconvertible only by complex, nonphysical multibond torsions—form a unique subset of atropisomers that differ from both canonical atropisomers (e.g., binaphthyls) and topoisomers (i.e., molecules that have identical connectivity but nonidentical molecular graphs). Small molecules, in contrast to biomacromolecules, are not expected to exhibit such ambiguous shapes. Using total synthesis, we found that the peptidic alkaloid tryptorubin A can be one of two noncanonical atropisomers. We then devised a synthetic strategy that drives the atropospecific synthesis of a noncanonical atrop-defined small molecule. Copyright © 2020 The Authors,
关键词	alkaloid tryptorubin A unclassified drug alkaloid connectivity molecular analysis peptide alkylation Article bioinformatics carbon nuclear magnetic resonance chemical structure chirality cyclization dehydrogenation high performance liquid chromatography hydrogen bond hydrophobicity isomerism nonhuman nuclear magnetic resonance spectroscopy oxidation priority journal protein processing proton nuclear magnetic resonance stereochemistry Streptomyces synthesis X ray crystallography
语种	英语
来源机构	Science
文献类型	期刊论文
条目标识符	http://gcip.llas.ac.cn/handle/2XKMVOVA/133767
推荐引用方式 GB/T 7714	Reisberg S.H.,Gao Y.,Walker A.S.,et al. Total synthesis reveals atypical atropisomerism in a small-molecule natural product, tryptorubin A[J]. Science,2020,367(6476).
APA	Reisberg S.H.,Gao Y.,Walker A.S.,Helfrich E.J.N.,Clardy J.,&Baran P.S..(2020).Total synthesis reveals atypical atropisomerism in a small-molecule natural product, tryptorubin A.,367(6476).
MLA	Reisberg S.H.,et al."Total synthesis reveals atypical atropisomerism in a small-molecule natural product, tryptorubin A".367.6476(2020).