Toglic And Angelic Acids

Buckles, Robert E.; Mock, Gene V.; Locatell, Louis

doi:10.1021/cr50004a002

Cited by 29 publications

(12 citation statements)

References 103 publications

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“…Experimentally, pure angelic acid tends to irreversibly convert to tiglic acid, which is more stable by 8.5 kcal/mol than angelic acid as deduced by heats of combustion. 52 Therefore, at 100 °C, our simulations suggest that an isovaline decomposition to angelic/ tiglic acid will result in an equilibrium ratio of about 10 −7 between products and reactants. We extended our metadynamics simulations to explore possible further evolution of angelic acid (7) toward decarboxylation, by explicitly targeting this reaction with extensive umbrella sampling simulations.…”

Section: ■ Resultsmentioning

confidence: 75%

Section: Decomposition Of Amino Acidsmentioning

confidence: 75%

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Hydrothermal Decomposition of Amino Acids and Origins of Prebiotic Meteoritic Organic Compounds

Pietrucci

Aponte

Starr

et al. 2018

ACS Earth Space Chem.

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The organic compounds found in carbonaceous chondrite meteorites provide insight into primordial solar system chemistry. Evaluating the formation and decomposition mechanisms of meteoritic amino acids may aid our understanding of the origins of life and homochirality on Earth. The amino acid glycine is widespread in meteorites and other extraterrestrial environments; other amino acids, such as isovaline, are found with enantiomeric excesses in some meteorites. The relationship between meteoritic amino acids and other compounds with similar molecular structures, such as aliphatic monoamines and monocarboxylic acids is unclear; experimental results evaluating the decomposition of amino acids have produced inconclusive results about the preferred pathways, reaction intermediates, and if the conditions applied may be compatible with those occurring inside meteoritic parent bodies. In this work, we performed extensive tandem metadynamics, umbrella sampling, and committor analysis to simulate the neutral mild hydrothermal decomposition mechanisms of glycine and isovaline and put them into context for the origins of meteoritic organic compounds. Our ab initio simulations aimed to determine free energy profiles and decomposition pathways for glycine and isovaline. We found that under our modeled conditions, methylammonium, glycolic acid, and sec-butylamine are the most likely decomposition products. These results suggest that meteoritic aliphatic monocarboxylic acids are not produced from decomposition of meteoritic amino acids. Our results also indicate that the decomposition of L-isovaline prefers an enantioselective pathway resulting in the production of (S)-sec-butylamine.

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Section: ■ Resultsmentioning

confidence: 75%

Section: Decomposition Of Amino Acidsmentioning

confidence: 75%

Hydrothermal Decomposition of Amino Acids and Origins of Prebiotic Meteoritic Organic Compounds

Pietrucci

Aponte

Starr

et al. 2018

ACS Earth Space Chem.

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“…Tiglic acid is not an exception—along with its derivatives, it is an important flavoring agent and fragrance additive. Tiglic acid can be used in the processes of manufacturing rum, caramel, bread, and fruit essences [ 4 ]. Its derivatives also exhibit potential anti-inflammatory [ 5 ] and antiproliferative activity [ 6 ].…”

Section: Introductionmentioning

confidence: 99%

Structural, Spectroscopic, Thermal, and Magnetic Properties of a New Dinuclear Copper Coordination Compound with Tiglic Acid

et al. 2021

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The first coordination compound of copper and tiglic acid named tetrakis(μ-tiglato)bis(tiglic acid)dicopper(II) was synthesized and crystallized from water solution. Its structure was determined and analyzed based on X-ray diffraction measurement. The paddle-wheel coordination system of the investigated compound was compared with other similar copper structures known in the literature. The Hirshfeld analysis was used for the detailed analysis of intermolecular interaction. The new compound was also characterized in terms of infrared absorption, thermal, and magnetic properties. The antiferromagnetic coupling of copper ions was found.

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“…These moieties are found in such diverse groups as pyrrolizidine alkaloids and cyanolipids. Tiglic (15) and angelic (16) acids and their derivatives are widespread (Buckles et al, 1955). These compounds are derived in plants from leucine ( Fig.…”

Section: From Mev Alonatementioning

confidence: 99%

Introduction to Terpenes

Seigler

1998

Plant Secondary Metabolism

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Toglic And Angelic Acids

Cited by 29 publications

References 103 publications

Hydrothermal Decomposition of Amino Acids and Origins of Prebiotic Meteoritic Organic Compounds

Hydrothermal Decomposition of Amino Acids and Origins of Prebiotic Meteoritic Organic Compounds

Structural, Spectroscopic, Thermal, and Magnetic Properties of a New Dinuclear Copper Coordination Compound with Tiglic Acid

Introduction to Terpenes

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