Pasteur and the art of chirality

Gál, J.

doi:10.1038/nchem.2790

Cited by 76 publications

(67 citation statements)

References 5 publications

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“…A solution to this puzzle may be the recent proposal that Pasteur's recognition of the chirality of the crystals may have been the result of his work as an artist, in lithography in particular. 7 Importantly, this factor had no connection to Laurent or other scientists.…”

Section: Pasteur's Ethics In the Matter Of Auguste Laurentmentioning

confidence: 99%

“…Late in 1847 or early in 1848, Pasteur began an investigation of the crystallography of natural (+)-tartaric acid ([+]-TA) (Figure 1), paratartaric acid (PTA), and some of their salts. 3,4,7,8 The chiral hemihedral crystals of sodium ammonium tartrate are shown in Figure 2. Today, we know that PTA is racemic TA.…”

Section: Introductionmentioning

confidence: 99%

“…Pasteur measured the optical rotation of the substances, and his findings on the crystals and optical activity led him to recognize that the molecules of TA are chiral. 3,4,7,8 The chiral hemihedral crystals of sodium ammonium tartrate are shown in Figure 2. Some of the hemihedral facets in the crystal images are labeled, eg, with h or b', etc.…”

Section: Introductionmentioning

confidence: 99%

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In defense of Louis Pasteur: Critique of Gerald Geison's deconstruction of Pasteur's discovery of molecular chirality

Gál

2019

Chirality

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Louis Pasteur discovered the phenomenon of molecular chirality, based on his studies of tartrate crystals. His finding remains one of the most important discoveries in the history of chemistry and a fundamentally important chemical phenomenon, with essential implications in biology. In his 1995 book The Private Science of Louis Pasteur, the eminent historian of science Gerald L.Geison was highly critical of much of Pasteur's work including his discovery of molecular chirality. The in-depth analysis provided in this article indicates, however, that the negative assessment of Pasteur's chirality work by Geison is entirely without scientific basis. Criticisms of Pasteur in the book for other "transgressions" in his chirality work, such as supposed influences of his personal biases and stubbornly held a priori notions, misrepresentation of his scientific work in his publications and lectures, and unethical and careerminded conduct, are also not supported by the evidence. Other troubling features of the book include a broad failure to assure accuracy in a variety of fundamental and important information, including errors in names, dates, events, referencing, indexing, and French-language text.

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Section: Pasteur's Ethics In the Matter Of Auguste Laurentmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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In defense of Louis Pasteur: Critique of Gerald Geison's deconstruction of Pasteur's discovery of molecular chirality

Gál

2019

Chirality

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“…[6] In contrast to enantiopure organic materials,w hich have specific requirements,r acemic systems have convenient properties,f or example,e ase of crystallization, and have therefore gained significance in recent years. [7] Since Pasteurs first observation of enantioselective crystal formation from ar acemic solution, termed conglomerates, [8,9] av ariety of crystalline packing arrangements originating from racemic mixtures have been reported (Scheme 1). [10][11][12] Racemic crystallography,s ince the first theoretical prediction of it in 1995, [13,14] has been widely applied for protein-structure determination and structural elucidation of nucleic acids in the past decade.…”

Section: Introductionmentioning

confidence: 99%

Metastable Chiral Azobenzenes Stabilized in a Double Racemate

et al. 2020

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The self‐assembly of chiral organic chromophores is gaining huge significance due to the abundance of supramolecular chirality found in natural systems. We report an interdigitated molecular assembly involving axially chiral octabrominated perylenediimide (OBPDI) which transfers chiral information to achiral aromatic moieties. The crystalline two‐component assemblies of OBPDI and electron‐rich aromatic units were facilitated through π‐hole⋅⋅⋅π donor–acceptor interactions, and the charge‐transfer characteristics in the ground and excited states of the OBPDI cocrystals were established through spectroscopic and theoretical techniques. The OBPDI cocrystals entail a remarkable homochiral segregation of P and M enantiomers of both molecular entities in the same crystal system, leading to twisted double‐racemic arrangements. Synergistically engendered cavities with the stored chiral information of the twisted OBPDI stabilize higher‐energy P/M enantiomers of trans‐azobenzene through non‐covalent interactions.

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“…In the first half of the XIX century Louis Pasteur discovered, during his studies about the optical characteristics of a well-known chemical compound largely investigated in oenology, i.e., the tartaric acid, the chirality. Pasteur, most known for his important researches on the veterinary medicine, human health, and agriculture, detailed the molecular chirality of the tartaric acid by means of crystallographic and optical activity characterizations starting a new direction in chemistry (Pasteur, 1853;Gal, 2017). Starting from Pasteur's observations, it was more and more clear that the 3-Dimensional configuration of organic molecules remarkably affects their chemical activity (Xiao et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Chiral Discrimination of D-Phenylalanine Amino Acid Based on a Perylene Bisimide Derivative

Bettini

Syrgiannis

Ottolini

et al. 2020

Front. Bioeng. Biotechnol.

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The interaction between homochiral substituted perylene bisimide (PBI) molecule and the D enantiomer of phenylalanine amino acid was monitored. Spectroscopic transitions of PBI derivative in aqueous solution in the visible range were used to evaluate the presence of D-phenylalanine. UV-visible, fluorescence, FT-IR, and AFM characterizations showed that D-phenylalanine induces significant variations in the chiral perylene derivative aggregation state and the mechanism is enantioselective as a consequence of the 3D analyte structure. The interaction mechanism was further investigated in presence of interfering amino acid (D-serine and D-histidine) confirming that both chemical structure and its 3D structure play a crucial role for the amino acid discrimination. A D-phenylalanine fluorescence sensor based on perylene was proposed. A limit of detection (LOD) of 64.2 ± 0.38 nM was calculated in the range 10 −7 -10 −5 M and of 1.53 ± 0.89 µM was obtained in the range 10 −5 and 10 −3 M.

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Pasteur and the art of chirality

Cited by 76 publications

References 5 publications

In defense of Louis Pasteur: Critique of Gerald Geison's deconstruction of Pasteur's discovery of molecular chirality

In defense of Louis Pasteur: Critique of Gerald Geison's deconstruction of Pasteur's discovery of molecular chirality

Metastable Chiral Azobenzenes Stabilized in a Double Racemate

Supramolecular Chiral Discrimination of D-Phenylalanine Amino Acid Based on a Perylene Bisimide Derivative

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