Triazolo-β-aza-ε-amino acid and its aromatic analogue as novel scaffolds for β-turn peptidomimetics

Bag, Subhendu Sekhar; Jana, Subhashis; Yashmeen, Afsana; De, Suranjan

doi:10.1039/c4cc08414d

Cited by 26 publications

(9 citation statements)

References 35 publications

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“…To produce a Boc‐protected amino derivative of 3‐ethynylaniline, following a reaction similar to that previously reported, tert ‐butyl(3‐iodophenyl)carbamate (see A in the Supporting Information Figure S3, 700 mg, 2.19 mmol) and [PdCl 2 (PPh 3 ) 2 ] (70 mg, 0.098 mmol) were solubilized in a mixture of benzene (30 mL) and n ‐butyl amine (20 mL) under an argon atmosphere and the solution was degassed by bubbling with argon gas for 10 m. Trimethylsilylacetylene (0.5 mL, 3.3 mmol, 1.5 equiv) and CuI (8.3 mg, 0.04 mmol) were added. The solution was stirred at 80 °C for 24 h. The solvents were evaporated by rotary evaporator and the crude of the reaction was dissolved in ethyl acetate (50 mL).…”

Section: Methodsmentioning

confidence: 99%

Grafting Behavior for the Resonating Variants of Ethynylaniline on Hydrogenated Silicon (100) Surfaces under Thermal Hydrosilylation

Tung

Tew

Coluccini

et al. 2018

Chemistry A European J

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This work reports the outcome of thermal grafting of 2-ethynylaniline, 3-ethynylaniline, and 4-ethynylaniline on a hydrogenated Si(100) surface. Using high-resolution XPS and AFM, it was found that the grafting of these compounds could be attributed to resonating structures that arise from the position of an electron-donating NH group and an electron-withdrawing acetylene group. For the ortho- and para-positioned acetylene group, surface reactions were observed to proceed predominantly via the acetylene to form a Si-C bond, whereas the meta-positioned acetylene group was found to have undergone nucleophilic grafting through the NH group onto the silicon surface to form a Si-N bond. Furthermore, a tert-butoxycarbonyl-protected derivative for a meta-positioned ethynylaniline was synthesized to exclusively force the reaction to react with the acetylene group and subsequent analysis confirmed that unprotected 3-ethynylaniline had indeed reacted through the nucleophilic NH group as hypothesized. Thus, for the first time, the interplay between resonance structures and their effects on silicon surface modifications were systematically catalogued.

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Section: Methodsmentioning

confidence: 99%

Grafting Behavior for the Resonating Variants of Ethynylaniline on Hydrogenated Silicon (100) Surfaces under Thermal Hydrosilylation

Tung

Tew

Coluccini

et al. 2018

Chemistry A European J

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“…In particular, the tendency of β-turn formation for this Tz amino acid system in tri and pentapeptides has been described. [17,18] It has been also shown that a 1,4-Tz amino acid can replace a dipeptide in an α-helical secondary structure. [19,20] Oligomers of triazole, also called triazolamers have been rarely described.…”

Section: Introductionmentioning

confidence: 99%

Fluorinated Triazole Foldamers: Folded or Extended Conformational Preferences

Arenas

Milcent

et al. 2021

ChemPlusChem

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Fluorinated peptidomimetic foldamers are still in their infancy. We report here the easy access to fluorinated triazolamers based on 2-amino-3,3,3-trifluoropropyl-1,4-triazolyl acetic acid (CF 3 À 1,4-Tz) and on aminomethyl-1,4-triazolyl-difluoroacetic acid (1,4-TzÀ CF 2). Both CF 3 À 1,4-Tz and 1,4-TzÀ CF 2 amino acids were efficiently prepared by copper(I)-catalyzed Huisgen 1,3dipolar cycloaddition. Their conformational preferences were studied by 2D NMR analyses and molecular dynamic simulations. Foldamers based on CF 3 À 1,4-Tz amino acids are capable of adopting short multi-stranded β-sheet-like structures that are maintained by electrostatic interactions between the triazole proton and N2 atom of neighboring subunits. On the contrary, foldamers based on 1,4-TzÀ CF 2 units adopt elongated β-strandlike structures, stabilized by electrostatic interaction between fluorine atoms and their neighboring protons.

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“…There have been two strategies of molecular design to mimic β-strand structures and hydrogen-bonding β-sheet structures. One is the use of nonpeptidic scaffolds to attain shape similarities to β-strand-like extended structures, − and the other is utilizing amino acids and amino acid surrogates to stabilize interstrand hydrogen-bonding β-sheet structures, which includes macrocyclization (backbone or side chain to side chain) and replacement of amino acids. − A major difference between these two strategies is the absence or presence of the ability to form interstrand hydrogen bonding. Many examples of the former approach have been reported using various nonamino acid units such as dibenzofurans, , oligoureas, − metallopeptides, − indolin-3-ones, imidazolidin-2-ones, epiindolines, and oligothienylpyridines .…”

Section: Introductionmentioning

confidence: 99%

Application of C-Terminal 7-Azabicyclo[2.2.1]heptane to Stabilize β-Strand-like Extended Conformation of a Neighboring α-Amino Acid

et al. 2018

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β-Strands are formed by extended linear peptide chains that are usually paired to form β-sheet structure through interstrand hydrogen bonding. Linking a structured organic molecule with α-amino acid(s) can enforce or stabilize β-strand-like extended structures of the jointed amino acids. Spectroscopic and simulation studies indicated that the presence of a C-terminal 7-azabicyclo[2.2.1]heptane amine (Abh) favors a β-strand-like extended conformation of the adjacent α-amino acid on the N side. The bridgehead substitution of the Abh unit biases the amide cis–trans equilibrium of the adjacent α-amino acid residue to cis conformation. The proximity, specified by the presence of bond paths (such as H–H bond path) between the bridgehead proton of Abh and the α-proton of the α-amino acid provides a driving force favoring the extended conformation, which is independent of solvents. These results provide a basis for de novo design of β-strand-mimicking extended peptides by using β-strand enforcer/stabilizer even in the absence of the interstrand hydrogen bonding.

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Triazolo-β-aza-ε-amino acid and its aromatic analogue as novel scaffolds for β-turn peptidomimetics

Cited by 26 publications

References 35 publications

Grafting Behavior for the Resonating Variants of Ethynylaniline on Hydrogenated Silicon (100) Surfaces under Thermal Hydrosilylation

Grafting Behavior for the Resonating Variants of Ethynylaniline on Hydrogenated Silicon (100) Surfaces under Thermal Hydrosilylation

Fluorinated Triazole Foldamers: Folded or Extended Conformational Preferences

Application of C-Terminal 7-Azabicyclo[2.2.1]heptane to Stabilize β-Strand-like Extended Conformation of a Neighboring α-Amino Acid

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