Structural Characterization of Chirality‐Organized Ferrocene–Dipeptide Conjugates that Contain Pyridine N‐Oxide Moieties,Asian Journal of Organic Chemistry

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Structural Characterization of Chirality‐Organized Ferrocene–Dipeptide Conjugates that Contain Pyridine N‐Oxide Moieties
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2017-05-26 , DOI: 10.1002/ajoc.201700145
Toshiyuki Moriuchi ₁ , Hao Wu ₁ , Yoshiki Tayano ₁ , Toshikazu Hirao ₁

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Two ferrocene–dipeptide conjugates, Fc(l‐Ala−l‐Pro−PyO)₂ (2) and Fc(l‐Ala−l‐Pro−PyO)₁ (3), were synthesized by the introduction of an l‐Ala−l‐Pro dipeptide that contained a C‐terminal pyridine N‐oxide moiety into the ferrocene organometallic scaffold. Single‐crystal X‐ray structure determination of ferrocene–dipeptide conjugate 2, which was composed of two dipeptide chains, confirmed the formation of intramolecular antiparallel β‐sheet‐like hydrogen bonds between the CO (Ala) and NH (Ala of another chain) groups to induce a chirality‐organized structure in which the ferrocenoyl moiety adopted a P‐helical chirality. In the crystal packing of compound 2, the peptide chains adopted a right‐handed molecular arrangement through hydrogen‐bonding interactions. On the contrary, ferrocene–dipeptide conjugate 3, which was composed of only one dipeptide chain, self‐assembled into a tetramer structure through the formation of intermolecular hydrogen bonds and π–π interactions between pyridine N‐oxide moieties.

中文翻译：

包含吡啶N-氧化物部分的手性组织的二茂铁-二肽结合物的结构表征

二茂铁二肽缀合物，FC（升-Ala-升-Pro杓）₂（2）和Fc（升-Ala-升-Pro杓）₁（3）中，通过引入一个的合成升-Ala −二茂铁有机金属支架中包含一个C末端吡啶N-氧化物部分的l- Pro二肽。二茂铁-二肽共轭物2的单晶X射线结构测定由两条二肽链组成，证实了在CO（Ala）和NH（另一条链的Ala）基团之间形成分子内反平行β-sheet-like氢键，从而诱导了手性组织的结构，其中采用了二茂铁酰基部分一个P螺旋手性。在化合物2的晶体堆积中，肽链通过氢键相互作用采用了右旋分子排列。相反，仅由一条二肽链组成的二茂铁-二肽共轭物3通过形成分子间氢键和吡啶N-氧化物部分之间的π-π相互作用而自组装成四聚体结构。

更新日期：2017-05-26

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