Seven-membered ring excited-state intramolecular proton-transfer in 2-benzamido-3- (pyridin-2-yl)acrylic acid

Guo, Zhaoqi; Chen, Weiqiang; Duan, Xuan‐Ming

doi:10.1016/j.dyepig.2011.06.004

Cited by 19 publications

(6 citation statements)

References 39 publications

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“…In Tables , we listed all published α‐amino acid derivatives and (either linear or, more rarely, cyclic) peptides to the decamer level where single or consecutive fully‐extended (C 5 ) structures were identified by X‐ray diffraction in the last 5/6 years. A few, still unpublished 3D‐structures, characterized by the C 5 form and solved in the Padova laboratory, are presented in Table…”

Section: Detailed Literature Survey On Peptides Since 2012mentioning

confidence: 99%

“…A few examples of C 5 structures involving a C α,β ‐didehydro‐α‐amino acid were reported since 2012 (Table ). One of them accommodates a ΔPyr (C α,β ‐didehydro‐pyridin‐2‐yl‐alanyl) residue, whereas all of the remaining C 5 structures are formed by ΔAla . Interestingly, in the structure of the macrocyclic antibiotic thiostrepton, two out of the three ΔAla residues occurring in the molecule are fully extended, one of them within the macrocyclic part and the other C‐terminal to the “tail”…”

Section: Detailed Literature Survey On Peptides Since 2012mentioning

confidence: 99%

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The fully‐extended conformation in peptides and proteins

et al. 2018

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The intramolecularly H‐bonded, fully‐extended conformation (C5) of an α‐amino acid residue (and the resulting 2.05‐helix obtained via its propagation) is one of the least extensively investigated types of peptide and protein backbone secondary structure. This situation does still currently occur despite its unique ability to enjoy by far the largest separation per residue among peptide conformations. In this article, we offer a detailed update of our present knowledge on this intriguing 3D‐structure of peptides in the crystal state as obtained from recently published investigations, complemented by a statistical analysis for its occurrence in the crystal structures of α‐amino acid derivatives and peptides available in the Cambridge Structural Database. We have expanded this useful information to the results of a bioinformatics analysis performed on this (so far largely unappreciated) conformation authenticated in all proteins solved by X‐ray diffraction to a resolution of ≤ 1.5 Å. In the last section, we describe the results of our DFT calculations on the conformational preferences of a set of homopeptides (from monomer to octamer) based on as many as six proteins and two noncoded, carefully selected, α‐amino acids. From this literature survey integrated by new energy calculations, we have definitely provided strong support to the thesis that this polypeptide 3D‐structure does indeed exist, it should be not neglected in future studies by structural biochemists, and it represents a very attractive, novel backbone for applications for organic, medicinal, and biomaterials chemists.

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Section: Detailed Literature Survey On Peptides Since 2012mentioning

confidence: 99%

Section: Detailed Literature Survey On Peptides Since 2012mentioning

confidence: 99%

The fully‐extended conformation in peptides and proteins

et al. 2018

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“…The starting materials such as 7-methoxy-2,3-dihydro-1H-inden-1-one (6), N-bromosuccinimide (NBS), 2,2 -azobisisobutyronitrile (AIBN), triethylamine, , , -tetrabromo-o-xylene, sodium iodide, boron tribromide, tert-butyl chloride, and aluminum trichloride were purchased from Merck, ACROS, and Sigma-Aldrich. Solvents were distilled freshly according to standard procedure.…”

Section: Chemicals and Instrumentsmentioning

confidence: 99%

“…Organic fluorescent molecules with excited-state intramolecular proton transfer (ESIPT) characteristics have been constantly drawing significant attention due to their peculiar optical properties [1][2][3][4][5][6]. An ESIPT reaction commonly involves the transfer of a hydroxyl (amino) proton to an acceptor such as imine nitrogen (carbonyl oxygen) through a preexisting hydrogen bonding configuration [7][8][9].…”

Section: Introductionmentioning

confidence: 99%

A White-Light-Emitting Small Molecule: Synthesis, Crystal Structure, and Optical Properties

Fang¹,

Tsai²,

Hu³

et al. 2014

International Journal of Photoenergy

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A white-light-emitting small molecule (1) was synthesized and characterized by single-crystal X-ray diffraction. Compound1undergoes an excited-state intramolecular proton transfer (ESIPT) reaction, resulting in a tautomer that is in equilibrium with the normal species and exhibiting a dual emission that covers almost all of the visible spectrum, and consequently generates white light. Furthermore, the geometric structures, the frontier molecular orbitals (MOs), and the potential energy curves for1in the ground and the first singlet excited state were fully rationalized by density functional theory (DFT) and time-dependent DFT calculations. The results show that the forward ESIPT and backward ESIPT may happen on the same timescale, enabling the excited-state equilibrium to be established.

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“…Excited-state intramolecular proton transfer (ESIPT) molecules have been drawing significant attention due to their unusual optical properties [ 1 , 2 , 3 , 4 , 5 , 6 ]. An ESIPT reaction usually involves the transfer of a hydroxyl proton to an acceptor such as carbonyl oxygen (imine nitrogen) through a pre-existing hydrogen bonding system [ 7 , 8 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray Structure, Optical, and Electrochemical Properties of a White-Light-Emitting Molecule

Tsai

et al. 2016

Materials

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A new white-light-emitting molecule (1) was synthesized and characterized by NMR spectroscopy, high resolution mass spectrometry, and single-crystal X-ray diffraction. Compound 1 crystallizes in the orthorhombic space group Pnma, with a = 12.6814(6), b = 7.0824(4), c = 17.4628(9) Å, α = 90°, β = 90°, γ = 90°. In the crystal, molecules are linked by weak intermolecular C-H···O hydrogen bonds, forming an infinite chain along [100], generating a C(10) motif. Compound 1 possesses an intramolecular six-membered-ring hydrogen bond, from which excited-state intramolecular proton transfer (ESIPT) takes place from the phenolic proton to the carbonyl oxygen, resulting in a tautomer that is in equilibrium with the normal species, exhibiting a dual emission that covers almost all of the visible spectrum and consequently generates white light. It exhibits one irreversible one-electron oxidation and two irreversible one-electron reductions in dichloromethane at modest potentials. Furthermore, the geometric structures, frontier molecular orbitals (MOs), and the potential energy curves (PECs) for 1 in the ground and the first singlet excited state were fully rationalized by density functional theory (DFT) and time-dependent DFT calculations. The results demonstrate that the forward and backward ESIPT may happen on a similar timescale, enabling the excited-state equilibrium to be established.

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Seven-membered ring excited-state intramolecular proton-transfer in 2-benzamido-3- (pyridin-2-yl)acrylic acid

Cited by 19 publications

References 39 publications

The fully‐extended conformation in peptides and proteins

The fully‐extended conformation in peptides and proteins

A White-Light-Emitting Small Molecule: Synthesis, Crystal Structure, and Optical Properties

Synthesis, X-ray Structure, Optical, and Electrochemical Properties of a White-Light-Emitting Molecule

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