Hydrogen bond design principles

Karas, Lucas J.; Wu, Chia‐Hua; Das, Ramkrishna; Wu, Judy I.

doi:10.1002/wcms.1477

Cited by 103 publications

(77 citation statements)

References 131 publications

(210 reference statements)

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“…Already in the 1950s Linus Pauling explored together with Robert B. Corey the importance of hydrogen bonding in proteins [ 46 , 47 , 48 ], work which contributed to his Nobel Price in Chemistry, awarded to him in 1954 for his research into the nature of the chemical bond and its application to the elucidation of the structure of complex substances [ 49 , 50 ]. Up to now HBs have been the object of numerous experimental and theoretical investigations [ 45 , 51 , 52 , 53 ], and because of the complex interplay between different components, their nature is still subject of an ongoing debate [ 41 , 42 , 54 ]. Using intermolecular HBs as the key feature of base pairs selectivity GC base pairs with different bonding patterns and atomic organization were suggested [ 55 , 56 ], as well as different UBP

estimating the HBs via calculated interaction energies [ 57 ].…”

Section: Introductionmentioning

confidence: 99%

Hydrogen Bonding in Natural and Unnatural Base Pairs—A Local Vibrational Mode Study

2021

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In this work hydrogen bonding in a diverse set of 36 unnatural and the three natural Watson Crick base pairs adenine (A)–thymine (T), adenine (A)–uracil (U) and guanine (G)–cytosine (C) was assessed utilizing local vibrational force constants derived from the local mode analysis, originally introduced by Konkoli and Cremer as a unique bond strength measure based on vibrational spectroscopy. The local mode analysis was complemented by the topological analysis of the electronic density and the natural bond orbital analysis. The most interesting findings of our study are that (i) hydrogen bonding in Watson Crick base pairs is not exceptionally strong and (ii) the N–H⋯N is the most favorable hydrogen bond in both unnatural and natural base pairs while O–H⋯N/O bonds are the less favorable in unnatural base pairs and not found at all in natural base pairs. In addition, the important role of non-classical C–H⋯N/O bonds for the stabilization of base pairs was revealed, especially the role of C–H⋯O bonds in Watson Crick base pairs. Hydrogen bonding in Watson Crick base pairs modeled in the DNA via a QM/MM approach showed that the DNA environment increases the strength of the central N–H⋯N bond and the C–H⋯O bonds, and at the same time decreases the strength of the N–H⋯O bond. However, the general trends observed in the gas phase calculations remain unchanged. The new methodology presented and tested in this work provides the bioengineering community with an efficient design tool to assess and predict the type and strength of hydrogen bonding in artificial base pairs.

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estimating the HBs via calculated interaction energies [ 57 ].…”

Section: Introductionmentioning

confidence: 99%

Hydrogen Bonding in Natural and Unnatural Base Pairs—A Local Vibrational Mode Study

2021

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“…According to the orbital interaction and the dipole–dipole interaction model, [ 45 ] it can be confirmed that hydrogen bond OH⋯O═C is stronger than OH⋯N owing to higher electronegativities of O (3.5) than N (3.0). [ 46 ] As a result, benefiting from more stable hydrogen bonding, the interface action and interfacial polarization can be enhanced for the BT–cCNT/PDMS composites, thereby leading to a relatively higher dielectric constant than that of BT–aCNT/PDMS as well as comparable dielectric loss. On the whole, tailor‐made dielectric features can be realized by the interaction between fillers via hydrogen bond.…”

Section: Resultsmentioning

confidence: 99%

Enhanced dielectric performance of polydimethylsiloxane‐based ternary composites films via tailored hydrogen bonds between carbon nanotube and barium titanate as modified fillers

Tang

Liu

Wang

et al. 2021

Vinyl Additive Technology

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A series of BT–cCNT/PDMS and BT–aCNT/PDMS composites were developed by incorporating barium titanate (BT) nanoparticles together with carboxylic functionalized multiwalled carbon nanotubes (cCNT) and amino functionalization multiwalled carbon nanotubes (aCNT) in polydimethylsiloxane (PDMS). Benefitting from the abundant active groups, CNTs and BTs can be in situ “bridged” by hydrogen bond in all of the BT–cCNT/PDMS and BT–aCNT/PDMS composites. Here, we studied the effect of hydrogen bonds (type and amount) between BTs and CNTs at the interface and dielectric properties of the composites. The results indicated that the BT–cCNT/PDMS composite exhibited higher dielectric constant and comparable dielectric loss than the BT–aCNT/PDMS composite, especially when weightCNT < 1 wt%. Also, the dielectric properties of BT–cCNT/PDMS composite show stronger temperature dependence than BT–aCNT/PDMS composite. Finally, the tailorable performance of the polymer‐based dielectric composites can be obtained by regulating the interface with the help of hydrogen bonds.

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“…It is well known that hydrogen bonds, unlike van der Waals forces, are saturated and directional. 19 The unique nature of hydrogen bonds significantly impacts the formation, particle size and polydispersity index (PDI) of U : C NPs. In particular, the molar ratios of U-SS-DOX and Ara-C might exert an influence on the supramolecular assembly process.…”

Section: Co-assembly Of U-ss-dox and Ara-c And Optimum Dose Ratio Screeningmentioning

confidence: 99%

Molecular recognition-driven supramolecular nanoassembly of a hydrophobic uracil prodrug and hydrophilic cytarabine for precise combination treatment of solid and non-solid tumors

Wang

et al. 2022

Nanoscale Horiz.

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Hydrogen bond design principles

Cited by 103 publications

References 131 publications

Hydrogen Bonding in Natural and Unnatural Base Pairs—A Local Vibrational Mode Study

Hydrogen Bonding in Natural and Unnatural Base Pairs—A Local Vibrational Mode Study

Enhanced dielectric performance of polydimethylsiloxane‐based ternary composites films via tailored hydrogen bonds between carbon nanotube and barium titanate as modified fillers

Molecular recognition-driven supramolecular nanoassembly of a hydrophobic uracil prodrug and hydrophilic cytarabine for precise combination treatment of solid and non-solid tumors

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