Chirality and helix stability of polyglutamic acid enantiomers

Kodona, Eleftheria K.; Alexopoulos, Charalambos; Panou‐Pomonis, Eugenia; Pomonis, P.J.

doi:10.1016/j.jcis.2007.10.063

Cited by 16 publications

(20 citation statements)

References 64 publications

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“…On the other hand, in 2008, Pomonis et al reported that the α-helical motif in poly-D-glutamic acid is stable thermally, compared to that of poly-L-glutamic acid. Pomonis et al ascribed this difference to an increased interaction of the L-species with more abundant ortho-water, in support of the Shinitzky's claim [70].…”

Section: Introductionmentioning

confidence: 92%

Mirror Symmetry Breaking in Helical Polysilanes: Preference between Left and Right of Chemical and Physical Origin

Fujiki

2010

Symmetry

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Abstract:From elemental particles to human beings, matter is dissymmetric with respect to mirror symmetry. In 1860, Pasteur conjectured that biomolecular handednesshomochirality-may originate from certain inherent dissymmetric forces existing in the universe. Kipping, a pioneer of organosilicon chemistry, was interested in the handedness of sodium chlorate during his early research life. Since Kipping first synthesized several Si-Si bonded oligomers bearing phenyl groups, Si-Si bonded high polymers carrying various organic groups-polysilanes-can be prepared by sodium-mediated condensation of the corresponding organodichlorosilanes. Among these polysilanes, optically active helical polysilanes with enantiomeric pairs of organic side groups may be used for testing the mirror symmetry-breaking hypothesis by weak neutral current (WNC) origin in the realm of chemistry and material science. Several theoretical studies have predicted that WNC-existing chiral molecules with stereogenic centers and/or stereogenic bonds allow for distinguishing between image and mirror image molecules. Based on several amplification mechanisms, theorists claimed that minute differences, though still very subtle, may be detectable by precise spectroscopic and physicochemical measurements if proper chiral molecular pairs were employed. The present paper reports comprehensively an inequality between six pairs of helical polysilane high polymers, presumably, detectable by (chir)optical and achiral 29 Si-/ 13 C-NMR spectra, and viscometric measurements.

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Section: Introductionmentioning

confidence: 92%

Mirror Symmetry Breaking in Helical Polysilanes: Preference between Left and Right of Chemical and Physical Origin

Fujiki

2010

Symmetry

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“…This non-mirror-image relation may be ascribed to some impurities, as claimed in several papers [68,71,73,117]. It may also infer other unknown reasons, such as an inherent mirror symmetry breaking at a global level upward, our universe scale [123,124] and macroscopic MPV effects [21,37,43,46,51,67,72,74]. The commercially available chiral alcohols shown above are very expensive compared to common chemicals.…”

Section: Optically Active Polymer Aggregates In the Ground Statementioning

confidence: 92%

“…Although it is already established that left-right symmetry is definitively broken at the elemental particle, subatomic and atomic levels [52][53][54][55][56][57][58][59][60][61][62][63][64][65][66], the detection of dissymmetry at the molecular level, so-called molecular parity violation (MPV), remains an unsolved issue. It is much debated whether the MPV hypothesis is valid and, even if it is true, whether it is detectable spectroscopically or by other acceptable methods [67][68][69][70][71][72][73][74][75][76].…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Chirality: Solvent Chirality Transfer in Molecular Chemistry and Polymer Chemistry

Fujiki

2014

Symmetry

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Controlled mirror symmetry breaking arising from chemical and physical origin is currently one of the hottest issues in the field of supramolecular chirality. The dynamic twisting abilities of solvent molecules are often ignored and unknown, although the targeted molecules and polymers in a fluid solution are surrounded by solvent molecules. We should pay more attention to the facts that mostly all of the chemical and physical properties of these molecules and polymers in the ground and photoexcited states are significantly influenced by the surrounding solvent molecules with much conformational freedom through non-covalent supramolecular interactions between these substances and solvent molecules. This review highlights a series of studies that include: (i) historical background, covering chiral NaClO 3 crystallization in the presence of D-sugars in the late 19th century; (ii) early solvent chirality effects for optically inactive chromophores/fluorophores in the 1960s-1980s; and (iii) the recent development of mirror symmetry breaking from the corresponding achiral or optically inactive molecules and polymers with the help of molecular chirality as the solvent use quantity.

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“…Their molecules contain one or more chiral carbons, i.e., stereo centers. The enantiomers exhibit identical chemical and physical properties in achiral environment, however, due to chiral centers the enantiomers are optically active and are able to rotate the plane of polarized light in the opposite direction, i.e., L and D or (+) and (-) or S and R enantiomers [1]. The racemic mixture contains both enantiomers in equal amounts.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Behavior of Nafion® Membranes towards (+)‐α‐Pinene and (−)‐α‐Pinene

et al. 2015

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a-Pinene enantiomers were sorbed in Nafion membranes. The membranes included a commercial extruded Nafion 115 membrane as well as membranes prepared by casting a Nafion solution, evaporating the solvent, and a thermal treatment at different temperatures. The microstructure of membranes was studied by small-angle and wide-angle X-ray scattering, and magic-angle spinning nuclear magnetic resonance spectroscopy. The change of membrane weight during the sorption process was determined with a sorption microbalance. Noticeable differences concerning the sorption behavior of the various membranes could be stated. The sorption of (+)-a-pinene and (-)-a-pinene in an extruded Nafion membrane turned out to be rather low.

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Chirality and helix stability of polyglutamic acid enantiomers

Cited by 16 publications

References 64 publications

Mirror Symmetry Breaking in Helical Polysilanes: Preference between Left and Right of Chemical and Physical Origin

Mirror Symmetry Breaking in Helical Polysilanes: Preference between Left and Right of Chemical and Physical Origin

Supramolecular Chirality: Solvent Chirality Transfer in Molecular Chemistry and Polymer Chemistry

Stereoselective Behavior of Nafion® Membranes towards (+)‐α‐Pinene and (−)‐α‐Pinene

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