Catenanes: Fifty Years of Molecular Links

Gil-Ramírez, Guzmán; Leigh, David A.; Stephens, Alexander J.

doi:10.1002/anie.201411619

Cited by 513 publications

(594 citation statements)

References 334 publications

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“…[25] Other groups have also been interested in chemical topology.I mpressive topologies at the molecular level have been reported by the research teams of Stoddart, Leigh, and Siegel, just to cite afew. [26][27][28] …”

Section: Chemical Topologymentioning

confidence: 99%

From Chemical Topology to Molecular Machines (Nobel Lecture)

2017

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To a large extent, the field of “molecular machines” started after several groups were able to prepare, reasonably easily, interlocking ring compounds (named catenanes for compounds consisting of interlocking rings and rotaxanes for rings threaded by molecular filaments or axes). Important families of molecular machines not belonging to the interlocking world were also designed, prepared, and studied but, for most of them, their elaboration was more recent than that of catenanes or rotaxanes. Since the creation of interlocking ring molecules is so important in relation to the molecular machinery area, we will start with this aspect of our work. The second part will naturally be devoted to the dynamic properties of such systems and to the compounds for which motions can be directed in a controlled manner from the outside, that is, molecular machines. We will restrict our discussion to a very limited number of examples which we consider as particularly representative of the field.

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Section: Chemical Topologymentioning

confidence: 99%

From Chemical Topology to Molecular Machines (Nobel Lecture)

2017

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“…Nowadays, aside from the mathematical perspective, the pursuit of topology has evolved into prominent themes in the physical and biological sciences 2,3 . However, the synthesis of topologically interesting molecules is still very challenging, both intellectually and technically [4][5][6] . In fact, the successful design and construction of topological structures at such small dimensions necessitates the controllable generation of nodes (or crossovers) in the precise position (how they are linked) and with the correct handedness (positive or negative).…”

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confidence: 99%

Creating complex molecular topologies by configuring DNA four-way junctions

2016

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The realization of complex topologies at the molecular level represents a grand challenge in chemistry. This necessitates the manipulation of molecular interactions with high precision. Here we show that single-stranded DNA (ssDNA) knots and links can be created by utilizing the inherent topological properties that pertain to the DNA four-way junction, at which the two helical strands form a node and can be configured conveniently and connected for complex topological construction. Using this strategy, we produced series of ssDNA topoisomers with the same sequences. By finely designing the curvature and torsion, double-stranded DNA knots were accessed by hybridizing and ligating the complementary strands with the knotted ssDNA templates. Furthermore, we demonstrate the use of a constructed ssDNA knot both to probe the topological conversion catalysed by DNA topoisomerase and to study the DNA replication under topological constraint.

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“…Catenanes are mechanically interlocked molecules and can be constructed from small organic molecules 1–2 as well as biopolymers, both natural 3–9 and engineered. 10–13 The central challenge of synthesizing any catenane structure is establishing the threading between the catenated rings.…”

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confidence: 99%

Self-Assembly of Catenanes from Lasso Peptides

Allen

Link

2016

J. Am. Chem. Soc.

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Lasso peptides exist naturally in a threaded state as [1]rotaxanes, and we reasoned that lasso peptides cleaved in their loop region could serve as building blocks for catenanes. Mutagenesis of the lasso peptide microcin J25 (MccJ25) with two cysteine residues followed by cleavage of the peptide with trypsin led to a [2]rotaxane structure that self-assembled into a [3]catenane and [4]catenanes at room temperature in aqueous solution. The [3]catenane represents the smallest ring size of a catenane comprised solely of polypeptide segments. The NMR structure of the [3]catenane was determined, suggesting that burial of hydrophobic residues may be a driving force for assembly of the catenane structure.

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Catenanes: Fifty Years of Molecular Links

Cited by 513 publications

References 334 publications

From Chemical Topology to Molecular Machines (Nobel Lecture)

From Chemical Topology to Molecular Machines (Nobel Lecture)

Creating complex molecular topologies by configuring DNA four-way junctions

Self-Assembly of Catenanes from Lasso Peptides

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