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	大环手性磷酰胺对氨基酸衍生物的分子识别研究; Studies on Molecular Recognition of Amino Acid Derivatives by Macrocyclic Chiral Phosphoramidates
	杜大明 ; 花文廷
	2003
关键词	磷酰胺 分子识别 大环化合物 phosphoramidate molecular recognition macrocyclic compound
英文摘要	以(S)-α-甲基苯乙胺和天然氨基酸(L-丙氨酸\, L-苯甘氨酸及L-苯丙氨酸)为手性源, 以2,5-二(邻羟基苯基)-1,3,4-二唑和2,4-二(邻羟基苯基)-1,3,5-二唑为刚性单元, 合成了一系列具有光学活性的新型含二唑磷酰胺和磷酯手性大环化合物. 用 NMR, IR 和FABMS 方法研究了所合成的手性大环对氨基酸甲酯盐酸盐和二肽的分子间相互作用和分子识别. 结果表明, 这些主体对D-或L-氨基酸甲酯盐酸盐和二肽具有选择性的结合作用.; In this paper, a series of new chiral macrocyclic phosphoramidates containing 2, 5-diaryl-1, 3, 4-oxadizole and (S)-methylbenzylamine and L-amino acid methyl ester units were synthesized and the structures were determined by H-1 NMR, MS, IR spectra and elemental analyses. FABMS, NMR and IR techniques were used to study the molecular recognition phenomena. The phosphoramidate molecules can form hydrogen bond or aromatic pi-pi interaction with D-phenylglycine, L-phenylglycine or L-phenylalanine methyl ester hydrochloride and dipeptide according to the appearance of 1+1 host guest molecular peak in FABMS spectra, NMR chemical shift and coupling constant changes. The chiral molecular recognition ability of chiral macrocyclic phosphoramidate for D-phenylglycine methyl ester hydrochloride is stronger than L-phenylglycine methyl ester hydrochloride. The side chain also affect the recognition ability, smaller substituent is better than larger substituent for the recongnition. As for the guest molecules, the D-phenylglycine and L-phenylglycine methyl ester hydrochloride are better than D- or L-phenylalanine methyl ester hydrochloride for the recongnition, no inclusion for the D- or L-alanine and L-histine methyl ester hydrochloride.; 国家自然科学基金; http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000182511900016&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701 ; SCI(E); 中文核心期刊要目总览(PKU); 中国科技核心期刊(ISTIC); 中国科学引文数据库(CSCD); 5; 3; 442-448; 24
语种	中文
出处	SCI ; 万方 ; http://d.g.wanfangdata.com.cn/Periodical_gdxxhxxb200303013.aspx
出版者	高等学校化学学报
内容类型	其他
源URL	[http://hdl.handle.net/20.500.11897/46990]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	杜大明,花文廷. 大环手性磷酰胺对氨基酸衍生物的分子识别研究, Studies on Molecular Recognition of Amino Acid Derivatives by Macrocyclic Chiral Phosphoramidates. 2003-01-01.

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