The effect of hydrogen bonding on the peptide linkage

Tor Ottersen
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引用次数: 3

Abstract

On the basis of the results obtained in a series of structure investigations and a series of theoretical studies the effect of hydrogen bonding on the peptide linkage (the NCO moiety) is discussed. The structure determinations., using X-ray diffraction methods, comprise eight molecules which contain the NCO moiety. The theoretical studies have been carried out using ab initio methods with hydrogen bonded complexes of formamide as model systems. The effect of hydrogen bonding on the peptide linkage, i.e. the shortening of the CN bond and the lengthening of the CO bond, is well reflected by the theoretical calculations. These calculations indicate that the readily delocalized π-electronic system, which can counteract perturbations in the σ-electronic system, is one of the major factors in the ability of the peptide linkage to form hydrogen bonds. On the basis of the structural parameters obtained in the crystal structure determinations and those found in the gaseous state for some simple amides, it is found that the formation of one intermolecular NH… O hydrogen bond, i.e. such that both the nitrogen and oxygen atoms of the NCO moiety are involved, leads to a shortening of the CN bond by ∼ 0.025 Å and a lengthening of the CO bond by ∼ 0.014 Å

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氢键对肽链的影响
在一系列结构研究和理论研究的基础上,讨论了氢键对肽链(NCO段)的影响。结构决定。利用x射线衍射方法,它由8个含有NCO部分的分子组成。以甲酰胺氢键配合物为模型体系,采用从头算方法进行了理论研究。理论计算很好地反映了氢键对肽链的影响,即CN键的缩短和CO键的延长。这些计算结果表明,π-电子系统的易离域性可以抵消σ-电子系统的扰动,是影响肽链形成氢键的主要因素之一。根据晶体结构测定得到的结构参数和一些简单酰胺的气态结构参数,发现分子间形成一个NH…O氢键,即NCO部分的氮原子和氧原子都参与其中,导致CN键缩短~ 0.025 Å, CO键延长~ 0.014 Å
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