Chirality Transfer through Helical Motifs in Coordination Compounds

He, Cheng; Zhao, Yonggang; Guo, Dong; Duan, Chunying

doi:10.1002/ejic.200700360

Cited by 98 publications

(50 citation statements)

References 106 publications

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“…Thus, Λ-stacking occurs between the 2,2'-bipyridyne ligands of the helicates. Such interactions are common in organometallic or DNA helices [23][24][25]. The handedness of the helices is induced by the intrinsic character of helicates: the enantiomer leads to the 31 helices while the Δ enantiomer leads to the 32 helices.…”

Section: Resultsmentioning

confidence: 99%

Packing of Helices: Is Chirality the Highest Crystallographic Symmetry?

Gautier

Poeppelmeier

2016

Crystals

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Chiral structures resulting from the packing of helices are common in biological and synthetic materials. Herein, we analyze the noncentrosymmetry (NCS) in such systems using crystallographic considerations. A comparison of the chiral structures built from helices shows that the chirality can be expected for specific building units such as 3 1 /3 2 or 6 1 /6 5 helices which, in hexagonal arrangement, will more likely lead to a chiral resolution. In these two systems, we show that the highest crystallographic symmetry (i.e., the symmetry which can describe the crystal structure from the smallest assymetric unit) is chiral. As an illustration, we present the synthesis of two materials ([Zn(2,2'-bpy) 3 ](NbF 6 ) 2 and [Zn(2,2'-bpy) 3 ](TaF 6 ) 2 ) in which the 3 n helices pack into a chiral structure.

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Section: Resultsmentioning

confidence: 99%

Packing of Helices: Is Chirality the Highest Crystallographic Symmetry?

Gautier

Poeppelmeier

2016

Crystals

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“…[1][2][3][4] However, since they are challenging to synthesise on a reasonable scale and have lability to proteases (leading to unfavourable pharmacokinetics) 2 there is a substantial effort to design and synthesise organic peptidomimetic and non-peptide mimetic systems. [5][6][7][8][9] The helicates [10][11][12][13][14][15][16][17][18] commonly comprise a chiral assembly of three ditopic bidentate organic ligands BA-AB around two metal centres, for example Fig. 1(a).…”

mentioning

confidence: 99%

Optically pure, water-stable metallo-helical ‘flexicate’ assemblies with antibiotic activity

et al. 2011

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The helicates--chiral assemblies of two or more metal atoms linked by short or relatively rigid multidentate organic ligands--may be regarded as non-peptide mimetics of α-helices because they are of comparable size and have shown some relevant biological activity. Unfortunately, these beautiful helical compounds have remained difficult to use in the medicinal arena because they contain mixtures of isomers, cannot be optimized for specific purposes, are insoluble, or are too difficult to synthesize. Instead, we have now prepared thermodynamically stable single enantiomers of monometallic units connected by organic linkers. Our highly adaptable self-assembly approach enables the rapid preparation of ranges of water-stable, helicate-like compounds with high stereochemical purity. One such iron(II) 'flexicate' system exhibits specific interactions with DNA, promising antimicrobial activity against a Gram-positive bacterium (methicillin-resistant Staphylococcus aureus, MRSA252), but also, unusually, a Gram-negative bacterium (Escherichia coli, MC4100), as well as low toxicity towards a non-mammalian model organism (Caenorhabditis elegans).

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“…conformation [17]. In this paper, although the chosen ligand L (C 4 H 3 O)CH@N-N@CH(C 4 H 3 O) contains four potential sites for coordination to metal ions, it is more favourable for coordination polymer formation through two more strongly binding imine N donors.…”

Section: Crystal Structure Of Ligand Lmentioning

confidence: 97%