Chapter 2. Design and Synthesis of Synthetic Receptors for Biomolecule Recognition

Diehl, Katharine L.; Bachman, James L; Chapin, Brette M.; Edupuganti, Ramakrishna; Escamilla, P Rogelio; Gade, A.; Hernandez, Erik T.; Jo, Hyun Hwa; Johnson, Amber; Kolesnichenko, Igor V.; Lim, Jaebum; Lin, Chung-Yon; Meadows, Margaret K.; Seifert, Helen M.; Zamora-Olivares, Diana; Anslyn, Eric V.

doi:10.1039/9781782622062-00039

Cited by 11 publications

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“…These reactions can be considered as intermediate between strong covalent bonds, which locks precursors into a specific arrangement, and of non-covalent interactions, which are often too dynamic to make discrete assemblies—unless they act cooperatively. 22 We focused on hydrazone formation with compound 4 for cyclic peptide ligand formation (Figure 3). Compound 4 served as a convenient branching point for grafting further structural complexity using dynamic covalent bonds.…”

Section: Resultsmentioning

confidence: 99%

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2,2′-Bipyridine and hydrazide containing peptides for cyclization and complex quaternary structural control

et al. 2018

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A synthetic peptide containing two Nε-methyl lysines (Ac-K(Nε-Me)GYTGYTGK(Nε-Me)D-OH) was alkylated with bipyridine (bipy) ligands substituted at the fifth (MP-5) and sixth (MP-6) positions, thereby creating Ac-K(Nε-Me, Nε-Bipy)GYTGYTGK(Nε-Me, Nε-Bipy)D-OH. Peptides with 6-position bipyridine did not bind to Fe2+ and Zn2+. Peptides with 5-position bipyridine bound these metals, and in the presence of one equivalent of a free bipy derivative folded into a macrocycle. Further, the free bipy derivative could also contain a cyclized peptide derived from hydrazone formation, resulting in complex but controlled quaternary peptide structure.

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Section: Resultsmentioning

confidence: 99%

“…Mono-methylation at the N-position of Lysine followed the indirect pathway 22 of mono-benzylation, then methylation via reductive amination with benzaldehyde and formaldehyde, respectively. The benzyl “protecting group” is then removed via palladium-catalyzed hydrogenolysis and replaced with a Boc protecting group for peptide synthesis.…”

Section: Methodsmentioning

confidence: 99%

2,2′-Bipyridine and hydrazide containing peptides for cyclization and complex quaternary structural control

et al. 2018

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“…15 Importantly, each FPBA and APBA derived iminoboronate or aminoboronate systems can exist either with a N / B dative bond or with a solvent inserted, and structural analysis via 11 B-NMR spectroscopy and crystallography can be performed to resolve the issue when it is critical to a full understanding of the chemistry. 16 An iminoboronate complex was rst reported by Dunn et al in 1968. 17 Thereaer, the James and Bull groups have shown fruitful utilization of this chemistry through chiral amine resolution in NMR, 18 and host-guest assembly in organic solvents.…”

Section: Iminoboronate Chemistrymentioning

confidence: 93%

“… 15 Importantly, each FPBA and APBA derived iminoboronate or aminoboronate systems can exist either with a N → B dative bond or with a solvent inserted, and structural analysis via 11 B-NMR spectroscopy and crystallography can be performed to resolve the issue when it is critical to a full understanding of the chemistry. 16 …”

Section: Iminoboronate Chemistrymentioning

confidence: 99%

Boronic acid based dynamic click chemistry: recent advances and emergent applications

2021

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“…Among the most commonly used macrocyclic host is cyclodextrin (CD), which is synthesized through cyclization of glucose polysaccharides with α-1,4-linkage and can have tunable cavity sizes ( Diehl et al, 2015 ; Wajs et al, 2016 ; Braegelman and Webber, 2019 ). The inner part of CDs is hydrophobic, whereas the outer part consists of hydroxyl moieties that facilitate water solubility.…”

Section: Supramolecular Systems As Recognition and Reporter Units For Biosensingmentioning

confidence: 99%

Evolution of Supramolecular Systems Towards Next-Generation Biosensors

2021

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Supramolecular materials, which rely on dynamic non-covalent interactions, present a promising approach to advance the capabilities of currently available biosensors. The weak interactions between supramolecular monomers allow for adaptivity and responsiveness of supramolecular or self-assembling systems to external stimuli. In many cases, these characteristics improve the performance of recognition units, reporters, or signal transducers of biosensors. The facile methods for preparing supramolecular materials also allow for straightforward ways to combine them with other functional materials and create multicomponent sensors. To date, biosensors with supramolecular components are capable of not only detecting target analytes based on known ligand affinity or specific host-guest interactions, but can also be used for more complex structural detection such as chiral sensing. In this Review, we discuss the advancements in the area of biosensors, with a particular highlight on the designs of supramolecular materials employed in analytical applications over the years. We will first describe how different types of supramolecular components are currently used as recognition or reporter units for biosensors. The working mechanisms of detection and signal transduction by supramolecular systems will be presented, as well as the important hierarchical characteristics from the monomers to assemblies that contribute to selectivity and sensitivity. We will then examine how supramolecular materials are currently integrated in different types of biosensing platforms. Emerging trends and perspectives will be outlined, specifically for exploring new design and platforms that may bring supramolecular sensors a step closer towards practical use for multiplexed or differential sensing, higher throughput operations, real-time monitoring, reporting of biological function, as well as for environmental studies.

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Chapter 2. Design and Synthesis of Synthetic Receptors for Biomolecule Recognition

Cited by 11 publications

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2,2′-Bipyridine and hydrazide containing peptides for cyclization and complex quaternary structural control

2,2′-Bipyridine and hydrazide containing peptides for cyclization and complex quaternary structural control

Boronic acid based dynamic click chemistry: recent advances and emergent applications

Evolution of Supramolecular Systems Towards Next-Generation Biosensors

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