Synthesis of rare sugar isomers through site-selective epimerization

doi:10.1038/s41586-020-1937-1

GSTDTAP > 地球科学

DOI	10.1038/s41586-020-1937-1
	Synthesis of rare sugar isomers through site-selective epimerization
	Jackson, Hartland W.1,2; Fischer, Jana R.1,2,3,4; Zanotelli, Vito R. T.1,2,3,4; Ali, H. Raza 1,2,5; Mechera, Robert 6,7; Soysal, Savas D.8,9; Moch, Holger 10; Muenst, Simone 11; Varga, Zsuzsanna 10; Weber, Walter P.6,7; Bodenmiller, Bernd 1,2
	2020-01-20
发表期刊	NATURE
ISSN	0028-0836
EISSN	1476-4687
出版年	2020
页码	403-+
文章类型	Article;Early Access
语种	英语
国家	USA
英文关键词	Glycans have diverse physiological functions, ranging from energy storage and structural integrity to cell signalling and the regulation of intracellular processes(1). Although biomass-derived carbohydrates (such as d-glucose, d-xylose and d-galactose) are extracted on commercial scales, and serve as renewable chemical feedstocks and building blocks(2,3), there are hundreds of distinct monosaccharides that typically cannot be isolated from their natural sources and must instead be prepared through multistep chemical or enzymatic syntheses(4,5). These ' rare' sugars feature prominently in bioactive natural products and pharmaceuticals, including antiviral, antibacterial, anticancer and cardiac drugs(6,7). Here we report the preparation of rare sugar isomers directly from biomass carbohydrates through site-selective epimerization reactions. Mechanistic studies establish that these reactions proceed under kinetic control, through sequential steps of hydrogen-atom abstraction and hydrogen-atom donation mediated by two distinct catalysts. This synthetic strategy provides concise and potentially extensive access to this valuable class of natural compounds. Various rare sugars that cannot be isolated from natural sources are synthesized using light-driven epimerization, a process which may find application in other synthetic scenarios.
领域	地球科学 ; 气候变化 ; 资源环境
收录类别	SCI-E
WOS记录号	WOS:000513110900001
WOS关键词	REGIOSELECTIVE OXIDATION ; D-ALLOSE ; EPIMERASE
WOS类目	Multidisciplinary Sciences
WOS研究方向	Science & Technology - Other Topics
引用统计
文献类型	期刊论文
条目标识符	http://119.78.100.173/C666/handle/2XK7JSWQ/281384
专题	地球科学资源环境科学气候变化
作者单位	1.Univ Zurich, Dept Quantitat Biomed, Zurich, Switzerland; 2.Univ Zurich, Inst Mol Life Sci, Zurich, Switzerland; 3.Swiss Fed Inst Technol, Life Sci Zurich Grad Sch, Zurich, Switzerland; 4.Univ Zurich, Zurich, Switzerland; 5.Univ Cambridge, CRUK Cambridge Inst, Cambridge, England; 6.Univ Basel, Dept Surg, Basel, Switzerland; 7.Univ Basel Hosp, Basel, Switzerland; 8.Univ Basel, Dept Biomed, Basel, Switzerland; 9.Clarunis Univ, Visceral Surg Res Lab, Dept Surg, Ctr Gastrointestinal & Liver Dis Basel, Basel, Switzerland; 10.Univ Hosp Zurich, Inst Pathol & Mol Pathol, Zurich, Switzerland; 11.Univ Hosp Basel, Inst Pathol & Genet, Basel, Switzerland
推荐引用方式 GB/T 7714	Jackson, Hartland W.,Fischer, Jana R.,Zanotelli, Vito R. T.,et al. Synthesis of rare sugar isomers through site-selective epimerization[J]. NATURE,2020:403-+.
APA	Jackson, Hartland W..,Fischer, Jana R..,Zanotelli, Vito R. T..,Ali, H. Raza.,Mechera, Robert.,...&Bodenmiller, Bernd.(2020).Synthesis of rare sugar isomers through site-selective epimerization.NATURE,403-+.
MLA	Jackson, Hartland W.,et al."Synthesis of rare sugar isomers through site-selective epimerization".NATURE (2020):403-+.