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	On the Electrophilicity of Cyclic Acylphosphoramidates (CAPAs) Postulated as Intermediates
	Ni, Feng ; Gao, Xiang ; Zhao, Zeng-Xiang ; Huang, Chao ; Zhao, Yu-Fen
	2010-10-12 ; 2010-10-12
关键词	Amino acids Bielectrophilicity NMR spectroscopy Phosphorus PHOSPHORYL AMINO-ACIDS AQUEOUS-SOLUTION N-CARBOXYANHYDRIDES PEPTIDE FORMATION ACETYL PHOSPHATE LEUCHS ANHYDRIDES HISTIDINE KINASES FORMYL PHOSPHATE CHEMISTRY MECHANISM Chemistry, Organic
中文摘要	Cyclic acylphosphoramidates (2-hydroxy-2-oxy-1,3,2-oxazaphospholidine-5-ones, CAPAs) are phosphate-activated amino acids possessing both a carboxyl-phosphoryl anhydride and a phosphoramidate bond in a ring. They structurally resemble NCAs (amino acid N-carboxyanhydrides, Leuchs' anhydrides), which have been extensively investigated. By contrast, the chemistry of CAPAs has remained almost unexplored since it was proposed in a prebiotic reaction of inorganic polyphosphates (Polyps) with amino acids. In the present work, the bielectrophilicity of alpha-CAPAs (Gly-CAPA, Ala-CAPA) was identified by isotopic analysis (O-18, N-15) and further proved by trapping alpha-CAPA with nucleophiles such as water, amino acids, phosphate and methanol in alkaline media, which yielded N-phosphoamino acids and peptide phosphoanhydride and phosphate ester derivatives. By comparison with the reactivity of NCAs, the bielectrophilicity of CAPAs indicates that CAPAs can provide rich chemistry. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weiriheim, Germany, 2009)
语种	英语 ; 英语
出版者	WILEY-V C H VERLAG GMBH ; WEINHEIM ; PO BOX 10 11 61, D-69451 WEINHEIM, GERMANY
内容类型	期刊论文
源URL	[http://hdl.handle.net/123456789/81068]
专题	清华大学
推荐引用方式 GB/T 7714	Ni, Feng,Gao, Xiang,Zhao, Zeng-Xiang,et al. On the Electrophilicity of Cyclic Acylphosphoramidates (CAPAs) Postulated as Intermediates[J],2010, 2010.
APA	Ni, Feng,Gao, Xiang,Zhao, Zeng-Xiang,Huang, Chao,&Zhao, Yu-Fen.(2010).On the Electrophilicity of Cyclic Acylphosphoramidates (CAPAs) Postulated as Intermediates..
MLA	Ni, Feng,et al."On the Electrophilicity of Cyclic Acylphosphoramidates (CAPAs) Postulated as Intermediates".(2010).

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