A MOLECULAR RECOGNITION MODEL FOR ENANTIOSELECTIVITY AND AUTOINDUCTION IN CYANOHYDRIN FORMATION CATALYZED BY CYCLO[(S)-HIS-(S)-PHE]

	A MOLECULAR RECOGNITION MODEL FOR ENANTIOSELECTIVITY AND AUTOINDUCTION IN CYANOHYDRIN FORMATION CATALYZED BY CYCLO[(S)-HIS-(S)-PHE]
	Wang JH
刊名	journal of theoretical & computational chemistry
	2010
卷号	9 期号:2 页码:495-510
关键词	ASYMMETRIC HYDROCYANATION SYNTHETIC DIPEPTIDES STATE STRUCTURES ORBITAL METHODS BASIS-SETS ALDEHYDES DYNAMICS ELECTRON CYCLO<(S)-PHENYLALANYL-(S)-HISTIDYL> CYCLO-<(S)-HIS-(S)-PHE>
ISSN号	0219-6336
通讯作者	wang jh
中文摘要	a molecular recognition mechanism based on dimeric model for cyclic dipeptide cyclo[(s)-his-(s)-phe] (abridged chp) catalyzed autoinduction is proposed according to the inference of previous experimental findings, which is supported by theoretical calculation with oniom(b3lyp/3-21g*:am1) method. the most unstable chp dimer whose intermolecular hydrogen bonds are immensely lessened by two intramolecular hydrogen bonds is defined as the highest active component (iia) existing in solid among the three possible dimers (ia, iia, and iib). the carbonyl group of benzaldehyde coordinates to chp dimer (iia) by a hydrogen bond with phe-n alpha h rather than his-n alpha h and hcn interacted with the imidazole moiety of his residue to form cyanide ion. in view of the theoretical calculation and experimental results, the structures of the nine-ring complexes derived from interaction between catalytic active dimer chp(iia) and cyanohydrins were postulated to explain the enantioselective autoinduction: the structure of no nitrile involved six-ring complex derived from interaction between catalytic active dimer chp(iia) and cyanohydrins were postulated to explain the elimination of enantioselective autoinduction.
收录类别	SCI收录期刊论文
语种	英语
WOS记录号	WOS:000279291900008
公开日期	2012-04-26
内容类型	期刊论文
源URL	[http://ir.ciac.jl.cn/handle/322003/43623]
专题	长春应用化学研究所_长春应用化学研究所知识产出_期刊论文
推荐引用方式 GB/T 7714	Wang JH. A MOLECULAR RECOGNITION MODEL FOR ENANTIOSELECTIVITY AND AUTOINDUCTION IN CYANOHYDRIN FORMATION CATALYZED BY CYCLO[(S)-HIS-(S)-PHE][J]. journal of theoretical & computational chemistry,2010,9(2):495-510.
APA	Wang JH.(2010).A MOLECULAR RECOGNITION MODEL FOR ENANTIOSELECTIVITY AND AUTOINDUCTION IN CYANOHYDRIN FORMATION CATALYZED BY CYCLO[(S)-HIS-(S)-PHE].journal of theoretical & computational chemistry,9(2),495-510.
MLA	Wang JH."A MOLECULAR RECOGNITION MODEL FOR ENANTIOSELECTIVITY AND AUTOINDUCTION IN CYANOHYDRIN FORMATION CATALYZED BY CYCLO[(S)-HIS-(S)-PHE]".journal of theoretical & computational chemistry 9.2(2010):495-510.