
Uwe J. Meierhenrich- Prof. Dr.
- Professor at Université Côte d'Azur
Uwe J. Meierhenrich
- Prof. Dr.
- Professor at Université Côte d'Azur
About
233
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Introduction
We perform experimental studies on the question why chiral organic molecules used in biological organisms occur in one (out of two) possible enantiomeric forms. We aim to understand the reason for biomolecular asymmetry. Therefore we participate in the cometary ROSETTA mission that aim to analyse cometary ices after landing on comet 67P/CG in 2014. Furthermore we subject racemic amino acids to circularly polarized synchrotron radiation to photochemically induce an enantiomeric enhancement.
Current institution
Additional affiliations
September 2005 - present
September 1997 - August 1999
Education
September 2005
September 2001 - August 2004
September 2000 - August 2001
Centre de Biophysique Moléculaire
Field of study
- Enantioselective Photolysis at synchrotron LURE
Publications
Publications (233)
Les études sur l’origine de la vie ont pour objectif de comprendre sa nature en explorant ses premières manifestations et ses complexités.Les premiers pas de la vie traite, dans un premier temps, de l’habitabilité de l’Univers et de la logique derrière la chimie prébiotique et ses modèles possibles et probables. L’ouvrage analyse ensuite le problèm...
Homochirality is a fundamental feature of all known forms of life, maintaining biomolecules (amino-acids, proteins, sugars, nucleic acids) in one specific chiral form. While this condition is central to biology, the mechanisms by which the adverse accumulation of non-l-α-amino-acids in proteins lead to pathophysiological consequences remain poorly...
The Philae lander of the Rosetta space mission made a non-nominal landing on comet 67P/Churyumov-Gerasimenko on November 12, 2014. Shortly after, using the limited power available from Philae’s batteries, the COSAC instrument performed a single 18-minutes gas chromatogram, which has remained unpublished until now due to the lack of identifiable elu...
The most pristine material of the Solar System is assumed to be preserved in comets in the form of dust and ice as refractory matter. ESA's mission Rosetta and its lander Philae had been developed to investigate the nucleus of comet 67P/Churyumov–Gerasimenko in situ. Twenty‐five minutes after the initial touchdown of Philae on the surface of comet...
The Philae lander of the Rosetta space mission made a non‐nominal landing on comet 67P/Churyumov‐Gerasimenko on November 12, 2014. Shortly after, using the limited power available from Philae's batteries, the COSAC instrument performed a single 18‐minutes gas chromatogram, which has remained unpublished until now due to the lack of identifiable elu...
The cometary Rosetta mission visited the nucleus of Comet 67P/Churyumov‐Gerasimenko by placing the Philae Lander on its surface. Philae was equipped with a time‐of‐flight mass spectrometer that analyzed, for the first time, cometary surface material in situ. Uwe J. Meierhenrich and co‐workers describe in their Research Article (DOI: 10.1002/anie.20...
Die Rosetta‐Kometenmission erforschte den Kern des Kometen 67P/Churyumov‐Gerasimenko durch Absetzen des Philae Lander auf der Kometenoberfläche. Philae war mit einem Flugzeit‐Massenspektrometer ausgestattet, mit dem erstmals das Material der Kometenoberfläche in situ analysiert wurde. Uwe J. Meierhenrich und Mitarbeiter beschreiben in ihrem Forschu...
The most pristine material of the Solar System is assumed to be preserved in comets in the form of dust and ice as refractory matter. ESA’s mission Rosetta and its lander Philae had been developed to investigate the nucleus of comet 67P/Churyumov‐Gerasimenko in situ. Twenty‐five minutes after the initial touchdown of Philae on the surface of comet...
The cover picture shows the Institut de Chimie de Nice (ICN), the chemistry research laboratory of the Université Côte d'Azur and the CNRS, which is located in the Parc Valrose in Nice, France. One‐hundred chemists work at the ICN, and are organized in four research teams: aroma, biomedical, radio‐, and material chemistry. This Editorial summarizes...
The ‘Institut de Chimie de Nice’ (ICN), founded in 2012, celebrates its 10th anniversary in 2022. Today, the ICN is part of the University Côte d'Azur (UCA), one out of nine excellence universities in France. ICN is also affiliated to the CNRS. We use the institute's anniversary to reflect on the origins and the successful evolution of research in...
Acyclic saturated hydrocarbon enantiomers were resolved by gas chromatography using a β-cyclodextrin-based chiral stationary phase. The stereospecific synthesis of single enantiomers of 4-methyloctane allowed to assign the absolute stereochemical configuration to the resolved enantiomers. Data show that the (S)-4-methyloctane shows higher chromatog...
Life on Earth employs chiral amino acids in stereochemical l-form, but the cause of molecular symmetry breaking remains unknown. Chiroptical properties of amino acids – expressed in circular dichroism (CD) – have been previously investigated in solid and solution phase. However, both environments distort the intrinsic charge distribution associated...
Homochiral proteins orchestrate biological functions throughout all domains of life, but the origin of the uniform l-stereochemistry of amino acids remains unknown. Here, we describe enantioselective adsorption experiments of racemic alanine and leucine onto homochiral d- and l-quartz as a possible mechanism for the abiotic emergence of biological...
Circularly polarised light (CPL) interacting with interstellar organic molecules might have imparted chiral bias and hence preluded prebiotic evolution of biomolecular homochirality. The l-enrichment of extra-terrestrial amino acids in meteorites, as opposed to no detectable excess in monocarboxylic acids and amines, has previously been attributed...
Circularly polarised light (CPL) interacting with interstellar organic molecules might have imparted chiral bias and hence preluded prebiotic evolution of biomolecular homochirality. The l-enrichment of extra-terrestrial amino acids in meteorites, as opposed to no detectable excess in monocarboxylic acids and amines, has previously been attributed...
The detection of biosignatures on Mars is of outstanding interest in the current field of Astrobiology and drives various fields of research, ranging from new sample collection strategies to the development of more sensitive detection techniques. Detailed analysis of the organic content in Mars analog materials collected from extreme environments o...
The most recent cometary space mission, Rosetta, carried instruments designed to characterize the organic molecules in comet 67P/Churyumov-Gerasimenko with unprecedented detail. The mass spectrometers revealed a great variety of molecules and indicate that 67P contains both primitive organic entities, probably from the parent molecular cloud of the...
The chemical composition of the essential oil of Saccocalyx satureioides Coss. et Dur. (Lamiaceae) was analyzed by chiral and achiral GC/MS and 42 components were identified. The main constituents were (+)-α-terpineol (35.9%), thymol (15.6%) and borneol (12.4%). The in vitro antibacterial and antifungal activities of the essential oil were assessed...
The chemical composition of the essential oil of Pituranthos chloranthus ssp. cossonianus Maire (Apiaceae) was investigated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) to reveal 54 compounds. The main constituents were myristicine (27.4%), limonene (15.8%), α-pinene (11.4%), and a-phellandrene (8.3%). The antibacteri...
The biomolecular homochirality in living organisms has been investigated for decades, but its origin remains poorly understood. It has been shown that circular polarized light (CPL) and other energy sources are capable of inducing small enantiomeric excesses (ees) in some primary biomolecules, such as amino acids or sugars. Since the first findings...
In the laboratory, the photo-and thermochemical evolution of ices, made of simple molecules of astrophysical relevance, always leads to the formation of semi-refractory water-soluble organic residues. Targeted searches for specific molecules do reveal the notable presence of two families of important molecular ''bricks of life'': amino acids, key m...
Vetiveryl acetate is a common ingredient of the perfume industry highly prized by perfumers for its crisp vetiver note and thus often used in high-end perfume compositions. Vetiveryl acetate is currently manufactured from vetiver oil by means of various industrial processes that result in the conversion of the main vetiver alcohols into their corre...
Philae is a comet Lander, part of the ESA Rosetta Mission to comet 67P/ChuryumovGerasimenko. After a ten year cruise through the solar system it successfully landed on the nucleus of the comet on November 12, 2014. Philae's payload consists of ten scientific instruments, including COSAC, an evolved gas analyser with the capability to differentiate...
Guaiacwood oil is a common perfume ingredient used in modern compositions for its suave woody-rosy scent. This essential oil is a byproduct of the timber industry obtained by hydrodistillation of the heartwood of Bulnesia sarmientoi, a tree native from Latin America. Despite being widely used in perfumery, guaiacwood oil has been poorly described i...
Living organisms on the Earth almost exclusively use l-amino acids for the molecular architecture of proteins. The biological occurrence of d-amino acids is rare, although their functions in various organisms are being gradually understood. A possible explanation for the origin of biomolecular homochirality is the delivery of enantioenriched molecu...
The Mars Organic Molecule Analyzer (MOMA) instrument onboard the ESA/Roscosmos ExoMars rover (to launch in July, 2020) will analyze volatile and refractory organic compounds in martian surface and subsurface sediments. In this study, we describe the design, current status of development, and analytical capabilities of the instrument. Data acquired...
The second ExoMars mission will be launched in 2020 to target an ancient location interpreted to have strong potential for past habitability and for preserving physical and chemical biosignatures (as well as abiotic/prebiotic organics). The mission will deliver a lander with instruments for atmospheric and geophysical investigations and a rover tas...
Guaiacwood oil from Bulnesia sarmientoi Lorentz ex. Griseb is a common natural ingredient of the perfume industry used in both domestic and luxury fragrances for its highly appreciated woody-rosy odor, as well as its excellent fixative properties. Despite its long and traditional use as a perfume ingredient, guaiacwood oil has not been extensively...
Oxford University Press 2016. 333 pp., hardcover, £ 22.99.—ISBN 978-0190275013
Oxford University Press 2016. 333 S., geb., 22.99 £.—ISBN 978-0190275013
This work presents the development of a simple and efficient analytical protocol for the direct enantioselective resolution of sugars. A racemic mixture of the C3 sugar d,l-glyceraldehyde and the C5 monosaccharides d,l-arabinose, d,l-ribose, d,l-xylose, and d,l-lyxose was subjected to derivatization with trifluoroacetic anhydride, and corresponding...
We detected ribose and related sugars in the organic residues of simulated interstellar ices using multidimensional gas chromatography. Kawai questions the formation of sugar compounds in the ices and suggests that they arise from a classical formose reaction during sample workup for analysis. We disagree with this hypothesis and present additional...
Since the pioneering work of Emanuel Gil-Av and his associates at the Weizmann Institute of Science the direct gas chromatographic resolution of enantiomers has found its application in different fields of natural sciences, even expanding to space research and astrobiology. In these domains the resolution of chiral molecules of prebiotic relevance...
Frankincense (olibanum) is one of the oldest aromatic materials used by humans, but the key molecular constituents contributing to its characteristic odor remained unknown. Reported herein is the discovery that (1S,2S)-(+)-trans- and (1S,2R)-(+)-cis-2-octylcyclopropyl-1-carboxylic acids are highly potent and substantive odorants occurring in ppm am...
Soluble and Insoluble Organic Matter is a key feature of primitive carbonaceous chondrites. We observe the formation of organic materials in the photo-thermochemical treatment of astrophysical ices in the laboratory. Starting from a low vacuum ultraviolet (VUV) irradiation dose on templates of astrophysical ices at 77 K, we obtain first a totally s...
Frankincense (olibanum) is one of the oldest aromatic materials used by humans, but the key molecular constituents contributing to its characteristic odor remained unknown. Reported herein is the discovery that (1S,2S)-(+)-trans- and (1S,2R)-(+)-cis-2-octylcyclopropyl-1-carboxylic acids are highly potent and substantive odorants occurring in ppm am...
This paper describes strategies to search for, detect, and identify organic material on the surface and subsurface of Mars. The strategies described include those applied by landed missions in the past and those that will be applied in the future. The value and role of ESA's ExoMars rover and of her key science instrument Mars Organic Molecule Anal...
Since the pioneering work of Emanuel Gil-Av and his associates at the Weizmann Institute of Science the direct gas chromatographic resolution of enantiomers has found its application in different fields of natural sciences, even expanding to space research and astrobiology. In these domains the resolution of chiral molecules of prebiotic relevance...
Photoelectron circular dichroism (PECD) manifests itself as an intense forward/backward asymmetry in the angular distribution of photoelectrons produced from randomly-oriented enantiomers by photoionization with circularly-polarized light (CPL). As a sensitive probe of both photoionization dynamics and of the chiral molecular potential, PECD attrac...
Making ribose in interstellar ices
Astrobiologists have long speculated on the origin of prebiotic molecules such as amino acids and sugars. Meinert et al. demonstrated that numerous prebiotic molecules can be formed in an interstellar-analog sample containing a mixture of simple ices of water, methanol, and ammonia. They irradiated the sample with...
This work presents an improved analytical procedure for the resolution and quantification of amino acid enantiomers by multidimensional gas chromatography. The procedure contains a derivatization step, by which amino acids were transformed into N(O,S)-ethoxycarbonylheptafluorobutyl esters. It was optimized for the resolution of non-proteinogenic am...
Stereoisomers of distinct chiral amino acids were observed to occur in l-enantioenriched form in carbonaceous chondrite meteorites. Meteoritic amines and monocarboxylic acids were recently shown to occur in racemic ratio. In this study we investigated the electronic circular dichroism and anisotropy spectra of chiral alcohols, chiral amines, and ch...
Astronomical observations of Centaurs and trans-Neptunian objects (TNOs) yield two characteristic features – near-infrared (NIR) reflectance and low geometric albedo. The first feature apparently originates due to complex organic material on their surfaces, but the origin of the material contributing to low albedo is not well understood. Titan thol...
The Philae Lander of ESA’s Rosetta Mission landed
succcessfully on, but immediately rebounded from, the
nucleus of comet 67P/Churyumov–Gerasimenko. Thereafter
the COmetary SAmpling and Composition Experiment
(COSAC), a pyrolysis Gas Chromatograph–Mass
Spectrometer, on board Philae made, while in resumed flight,
unique mass spectral measurements of...
The rose species Rosa damascena and Rosa centifolia are cultivated for their use as perfume raw materials. The solvent extract of rose petals provides the concrete that is further transformed into the absolute. Both, concrete and absolute contain a variety of organic molecules. As a result of the lack of an adequate analytical procedure and the com...
Comets harbor the most pristine material in our solar system in the form of ice, dust, silicates, and refractory organic material with some interstellar heritage. The evolved gas analyzer Cometary Sampling and Composition (COSAC) experiment aboard Rosetta's Philae lander was designed for in situ analysis of organic molecules on comet 67P/Churyumov-...
Comets harbor the most pristine material in our solar system in the form of ice, dust, silicates, and refractory organic material with some interstellar heritage. The evolved gas analyzer Cometary Sampling and Composition (COSAC) experiment aboard Rosetta’s Philae lander was designed for in situ analysis of organic molecules on comet 67P/ Churyumov...
This study investigates the concentrations of 54 multiclass pesticides during the transformation processes from rose petal to concrete and absolute using roses spiked with pesticides as a model. The concentrations of the pesticides were followed during the process of transforming the spiked rose flowers from an organic field into concrete and then...
In this paper data recorded by the Cometary Sampling and Composition experiment (COSAC), a pyrolysis - gas-chromatograph - mass-spectrometer (pyr GC-MS) aboard Philae are presented. After landing in a somewhat non-nominal way on the cometary nucleus of 67/P, Philae carried out its First Science Sequence. As part of these activities COSAC acquired s...
All life on Earth is characterized by its asymmetry - both the genetic material and proteins are composed of homochiral monomers. Understanding how this molecular asymmetry initially arose is a key question related to the origins of life. Cometary ice simulations, L-enantiomeric enriched amino acids in meteorites and the detection of circularly pol...
Significance
In molecular clouds out of which stars and planetary systems form, simple solid-state molecules made in large part of H 2 O, CO, CO 2 , CH 3 OH, and NH 3 are abundantly present. In these environments, energetic and thermal processes on these ices, which can be simulated in the laboratory, lead to complex organic matter. Possibly at the...
Comprehensive two-dimensional gas chromatography-mass spectrometry (GC × GC-MS) has been shown to permit for the unprecedented chromatographic resolution of volatile analytes encompassing various families of organic compounds. However, peak identification based on retention time, two-dimensional mapping, and mass spectrometric fragmentation only, i...
Divided into two parts, the first four chapters of Comets and their Origin refer to comets and their formation in general, describing cometary missions, comet remote observations, astrochemistry, artificial comets, and the chirality phenomenon.
The second part covers the cometary Rosetta mission, its launch, journey, scientific objectives, and ins...
Divided into two parts, the first four chapters of Comets and their Origin refer to comets and their formation in general, describing cometary missions, comet remote observations, astrochemistry, artificial comets, and the chirality phenomenon. The second part covers the cometary ROSETTA mission, its launch, journey, scientific objectives, and inst...
So this was in 1997, the Rosetta mission launched in March 2004, and Philae landed on the comet in November 2014 and sent data back. What did you do in the meantime? So it is still very exciting. Why do you think the Rosetta mission is not only a huge success for ESA and European science, but also very popular?
Das uns bekannte Leben kontrolliert den ausschließlichen Gebrauch von L-Aminosäure- und D-Zucker-Enantiomeren zum molekularen Aufbau von Proteinen und Nukleinsäuren. In diesem Kurzaufsatz wird aktuellen Modellen zum Symmetriebruch in Biomolekülen nachgegangen, die den Transport erdäußerer präbiotischer Moleküle umfassen. Der Kurzaufsatz stellt Enan...
Life, as it is known to us, uses exclusively L-amino acid and D-sugar enantiomers for the molecular architecture of proteins and nucleic acids. This Minireview explores current models of the original symmetry-breaking influence that led to the exogenic delivery to Earth of prebiotic molecules with a slight enantiomeric excess. We provide a short ov...
A series of eleven β-santalol analogs, including nine new derivatives, was prepared by semisynthesis from natural (−)-(Z)-β-santalol and studied by gas chromatography-olfactometry (GC-O) to characterize their olfactory properties and potencies. These compounds and 45 others selected in the literature were used to build three olfactophores by molecu...
With the European Space Agency's Rosetta space mission to comet 67P/Churyumov-Gerasimenko, a gas chromatograph, part of the COmetary Sampling And Composition (COSAC) experiment, travelled for about 10 years in the interplanetary medium before operating at the surface of the cometary nucleus in November 2014. During its journey in space, the instrum...
Vetiver oil is a highly esteemed basic ingredient of modern perfumery, but the nature of the constituents that really impart its typical and most sought woody-earthy scent has remained controversial. Indeed, vetiver oil is considered as one of the most complex essential oils, being mostly composed of several hundreds of sesquiterpene derivatives wi...
Damascena and centifolia roses are cultivated worldwide for their petal extracts that contain key odorant ingredients of perfumes. The analytical identification and quantification of pesticides in rose petals have never been described in the literature. Here, we report on a newly developed method using dispersive solid-phase extraction (d-SPE) clea...
The basic units that constitute essential biopolymers (proteins and nucleic acids) are enantiomerically biased. Proteins are constructed from L-amino acids and nucleic acids possess a backbone composed exclusively of D-sugars. Photochirogenesis has been postulated to be the source of this homochirality of biomolecules: Asymmetric photochemical reac...
The quantitative resolution of amino acid enantiomers is crucial to a number of fields of bioanalytical chemistry, including food and plant analysis, metabolomics, medicinal chemistry, and archeochemistry. The enantioselective analysis of α-dialkyl amino acids, however, has proven more difficult than for proteinaceous α-protonated amino acids. Here...
The discovery of meteoritic amino acids with enantiomeric excesses of the L-form (ee L) has suggested that extraterrestrial organic materials may have contributed to prebiotic chemistry and directed the initial occurrence of the ee L that further led to homochirality of amino acids on Earth. A proposed mechanism for the origin of ee L in meteorites...
The chemistry of life is purely stereospecific. The fundamental biopolymers – proteins and nucleic acids – are intrinsically chiral due to their molecular building blocks, namely L-amino acids and D-sugars. Hypotheses for the evolutionary origin of that strict stereochemical selection include the asymmetric photochemistry model by which circularly...
Circularly polarized light (CPL) is known to be a true chiral entity capable of generating absolute molecular asymmetry. However, the degree of inducible optical activity depends on the λ of the incident CPL. Exposure of amorphous films of rac-alanine to tunable CPL led to enantiomeric excesses (ee) which not only follow the helicity but also the e...
The European Space Agency’s Rosetta mission was launched in March 2004 in order to reach comet 67P/Churyumov–Gerasimenko by August 2014. The Cometary Sampling and Composition experiment (COSAC) onboard the Rosetta mission’s lander “Philae” has been designed for the cometary in situ detection and quantification of organic molecules using gas chromat...
Molek?le aus dem All;Weltall;RNA-Vorl?ufer;Kometen
All biopolymers are composed of homochiral building blocks, and both D-sugars and L-amino acids uniquely constitute life on Earth. These monomers were originally enantiomerically differentiated under prebiotic conditions. Particular progress has recently been made in support of the photochemical model for this differentiation: the interaction of ci...
Natural extracts used by the fragrance and cosmetics industries, namely essential oils, concretes, resinoids, and absolutes, are produced from natural raw materials. These are often cultivated by use of monoculture techniques that involve the use of different classes of xenobiotica, including pesticides. Because of these pesticides’ potential effec...
‘How did life start on Earth?’ and ‘Why were left-handed amino acids selected for the architecture of proteins?’ A new attempt to answer these questions of high public and interdisciplinary scientific interest will be provided by this review. It will describe most recent experimental data on how the basic and molecular building blocks of life, amin...
The introduction and development of comprehensive two-dimensional gas chromatography offers greatly enhanced resolution and identification of organic analytes in complex mixtures compared to any one-dimensional separation technique. Initially promoted by the need to resolve highly complex petroleum samples, the technique's enormous separation power...
Die umfassende zweidimensionale Gaschromatographie ermöglicht gegenüber jedweder eindimensionalen Trennmethode eine erhöhte Auflösung und eine verbesserte Identifizierung organischer Analyten in komplexen Mischungen. Ursprünglich zum Auflösen hochkomplexer Erdölproben eingeführt, zogen die enorme Trennleistung und die Möglichkeit zum Gewinn weitere...
Amino acids are the fundamental building blocks of proteins, the biomolecules that provide cellular structure and function in all living organisms. A majority of amino acids utilized within living systems possess pre-specified orientation geometry (chirality); however the original source for this specific orientation remains uncertain. In order to...
A simple, sensitive, selective, precise, and robust high-performance thin-layer chromatography (HPTLC) method was developed and validated for the quantification of vanillin beta-D-glucoside, p-hydroxybenzoic acid (APHB), vanillic acid, p-hydroxybenzaldehyde (PHB), and vanillin in vanilla fruits, beans, and extracts. The analysis was performed on HP...
On 10 July 2010 the Rosetta spacecraft flew-by asteroid Lutetia. At that
time all the mass spectrometers in the payload of the Philae Lander
capable of gas analysis were in operation. Among these, the COSAC
(Cometary Sampling and Composition) experiment is a gas-chromatograph
mass spectrometer which was switched on twice during the fly-by, once 3
h...
The primordial appearance of chiral amino acids was an essential component of the asymmetric evolution of life on Earth. In this tutorial review we will explore the original life-generating, symmetry-breaking event and summarise recent thoughts on the origin of enantiomeric excess in the universe. We will then highlight the transfer of asymmetry fr...
Light on chirality: To predict the enantiomeric enrichment that can be induced into racemic organic molecules with the help of circularly polarized light, the anisotropy factor g is essential. Anisotropy spectra g=f(λ) recorded for proteinaceous amino acids provide crucial information on the transfer of chirality from light to matter.
Biopolymere wie Proteine und Nukleinsäuren sind aus enantiomerenreinen Monomeren aufgebaut. [1] Der Ursprung des biomolekularen Symmetriebruchs – ein entscheidender Schritt für den Beginn allen Lebens auf der Erde – ist bisher nicht bekannt. Neben verschiedenen zufälligen [2] und deter-ministischen [3] Hypothesen schlägt ein weit verbreitetes photo...
A simple, fast, and efficient High-Performance Thin-Layer Chromatography (HPTLC) method was developed for the simultaneous quantitative determination of alcohols and acetates in Haitian vetiver essential oils (Chryzopogon zizanioides) and its acetylated form. Analytes were separated by using a mixture of n-hexane-chloroform-ethyl acetate (8:6:0.5,...
Interstellar ices were simulated by condensing and UV irradiating molecules such as H2O, CH3OH, and NH3 at 80 K. Multidimensional gas chromatography analyses allowed for the identification of 26 amino and diamino acids (see graph). The results support the suggestion that potentially prebiotic molecules originating from the photochemistry of interst...
A new, simple, sensitive, selective, precise, and robust high-performance thin-layer chromatography (HPTLC) method was developed and validated for the determination of nicotine in tobacco extracts. The analysis of nicotine was performed on thin-layer chromatography (TLC) glass plates precoated with silica gel 60 F254 as stationary phase. Developmen...