Site-to-site peptide transport on a molecular platform using a small-molecule robotic arm

Kassem, Salma; Lee, Alan T. L.; Leigh, David A.; Markevicius, Augustinas; Tetlow, Daniel J.; Toriumi, Naoyuki

doi:10.1039/d0sc05906d

Cited by 11 publications

(8 citation statements)

References 50 publications

(64 reference statements)

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“…Intramolecular motion triggered by light or chemical fuels is a driving force of artificial molecular switches [1–8] . The concept of controlled E/Z isomerization allows a challenging design of molecular architectures performing specific functions such as unidirectional rotation and intramolecular cargo transport [9–13] . Recently, Leigh and co‐workers [9] have demonstrated selective small‐molecule cargo transport by repositioning of 3‐mercaptopropanehydrazide in either direction between two sites 2 nm apart.…”

Section: Methodsmentioning

confidence: 99%

“…This was achieved by incorporating a quinoline unit into a rigid platform through a hydrazone group linkage to the rotor in order to control the directional movement of the mechanical arm. By using a similar rigid platform, they have successfully studied programmable mono, di‐ and tripeptide cargo transport using acid input as a fuel [11] . Despite the impressive achievement of bidirectional molecular transport by using a hydrazone bond, the development of new architectures is still a challenging field [10,11] .…”

Section: Methodsmentioning

confidence: 99%

“…By using a similar rigid platform, they have successfully studied programmable mono, di‐ and tripeptide cargo transport using acid input as a fuel [11] . Despite the impressive achievement of bidirectional molecular transport by using a hydrazone bond, the development of new architectures is still a challenging field [10,11] . Conditions for a rapid, strictly controlled, and reversible change to an end state, fuelled by light or chemically can be achieved through an appropriate molecular design [16,17] .…”

Section: Methodsmentioning

confidence: 99%

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Acylhydrazone Subunits as a Proton Cargo Delivery System in 7‐Hydroxyquinoline

Nakashima

Petek

Hori

et al. 2021

Chemistry A European J

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The reimagined concept of long‐range tautomeric proton transfer using crane subunits is shown by designing and synthesising two new acylhydrazones containing a 7‐hydroxyquinoline (7‐OHQ) platform. The acylhydrazone subunits attached to the 7‐OHQ at the 8th position act as crane arms for delivering proton cargo to the quinoline nitrogen. Light‐induced tautomerization to their keto forms leads to Z/E isomerization of the C=C axle bond, followed by proton delivery to the quinoline nitrogen by the formation of covalent or hydrogen bonds. The axle‘s being either an imine or ketimine bond is the structural difference between the studied compounds. The −CH3 group in the latter provides steric strain, resulting in different proton transport pathways. Both compounds show long thermal stability in the switched state, which creates a tuneable action of bidirectional proton cargo transport by using different wavelengths of irradiation. Upon the addition of acid, the quinoline nitrogen is protonated; this results in E/Z configuration switching of the acylhydrazone subunits. This was proven by single‐crystal X‐ray structure analysis and NMR spectroscopy.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Acylhydrazone Subunits as a Proton Cargo Delivery System in 7‐Hydroxyquinoline

Nakashima

Petek

Hori

et al. 2021

Chemistry A European J

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show abstract

“…Recently, Leigh and co-workers have studied selective small-molecule cargo transport over a 2 nm distance by incorporating a quinoline unit into a rigid platform through a hydrazone group linkage to the rotor . By using a similar rigid platform, they have successfully studied programmable mono, di-, and tripeptide cargo transport using acid input as a fuel …”

Section: Introductionmentioning

confidence: 99%

“…45 By using a similar rigid platform, they have successfully studied programmable mono, di-, and tripeptide cargo transport using acid input as a fuel. 46 Our recent studies on proton cargo transport to the N quin site in 7-OHQ platform have been focused on the synthesis and investigation of acylhydrazones and Schiff bases units, acting as proton crane-arms 47,48 (Scheme 2A,B). The structural differences in the axle unit of acylhydrazones using imine or ketimine bonds result in different proton transport pathways: (i) light-fueled site-to-site proton transport by intramolecular dynamic covalent bonding to the K2QH form in the imine acylhydrazone, and (ii) the −CH 3 steric strained crane demonstrates a proton delivery to the N quin site stabilized by IMHBI in the K2E form 47 (Scheme 2A).…”

Section: ■ Introductionmentioning

confidence: 99%

Solvent-Triggered Long-Range Proton Transport in 7-Hydroxyquinoline Using a Sulfonamide Transporter Group

et al. 2022

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The ability of long-range proton transport by substitution of 7-hydroxyquinoline at the eighth position with sulfonamide and sulfonylhydrazone rotor units to act as a cranearm has been studied. Different proton transport pathways triggered by different stimuli have been established depending on the structure of the crane-arms. Solvent-driven proton switching from OH to the quinoline nitrogen (N quin ) site, facilitated by a sulfonamide transporter group in polar protic and aprotic solvents, has been confirmed by optical (absorption and fluorescence) and NMR spectroscopies as well as by single-crystal X-ray structure analysis. Photoinduced long-range proton transport to the N quin site upon 340 nm UV light irradiation has been estimated in sulfonylhydrazone, which is not sensitive to solvent-driven switching. Both compounds have exhibited acid-triggered switching by trifluoroacetic acid due to the formation of a stable six-membered intramolecular hydrogen bonding interaction between the protonated N quin and crane-arm. The structures of acid-switched form were confirmed by NMR spectroscopy and single-crystal X-ray structure analysis. The behavior of the compounds suggests a big step forward in the advanced proton pump-switching architecture because they cover three distinct driving forces in the switching process: solvent, light, and acid.

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Zeolitic Imidazolate Frameworks as Solid‐State Nanomachines

Nam,

Kim,

Jin

et al. 2024

Angewandte Chemie

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Machines have continually developed with the needs of daily life and industrial applications. While the careful design of molecular‐scale devices often displays enhanced properties along with mechanical movements, controlling mechanics within solid‐state molecular structures remains a significant challenge. Here, we explore the distinct mechanical properties of zeolitic imidazolate frameworks (ZIFs) – frameworks that contain hidden mechanical components. Using a combination of experimental and theoretical approaches, we uncover the machine‐like capabilities of ZIFs, wherein connected composite building units operate similarly to a mechanical linkage system. Importantly, this research suggests that certain ZIF subunits act as core mechanical components, paving an innovative view for the future design of solid‐state molecular machines.

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Site-to-site peptide transport on a molecular platform using a small-molecule robotic arm

Abstract: Peptides are transported in either direction between chemically similar sites on a molecular platform, substrate repositioning is achieved using a cysteine hydrazide transporter module and a small-molecule robotic arm controlled by a rotary switch.

Cited by 11 publications

References 50 publications

Acylhydrazone Subunits as a Proton Cargo Delivery System in 7‐Hydroxyquinoline

Acylhydrazone Subunits as a Proton Cargo Delivery System in 7‐Hydroxyquinoline

Solvent-Triggered Long-Range Proton Transport in 7-Hydroxyquinoline Using a Sulfonamide Transporter Group

Zeolitic Imidazolate Frameworks as Solid‐State Nanomachines

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