Analytical TMAH pyrolysis of dipeptides: Formation of new complex cyclic compounds related to the presence of the peptide bond

Templier, Joëlle; Gallois, Nicolas; Derenne, Sylvie

doi:10.1016/j.jaap.2013.09.017

Cited by 7 publications

(9 citation statements)

References 28 publications

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“…The formation of more complex diketopiperazines was proposed by Templier et al . () from tripeptide units. A similar mechanism can be invoked for the formation of compound 19 from valine, as well as compounds 20 and 21 from serine and leucine (Table ; Cincotta et al .…”

Section: Resultsmentioning

confidence: 99%

“…Imidazolidinedione 12 probably results from the internal cyclization of tripeptide comprising an alanine unit as reported by Templier et al . (; Cincotta et al . , fig.…”

Section: Resultsmentioning

confidence: 99%

“…; Templier et al . ) and GC retention times. The molecular structure of all compounds present in substantial amount was investigated without any ion selection that could have biased interpretations.…”

Section: Methodsmentioning

confidence: 99%

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Chemical preservation of tail feathers fromAnchiornis huxleyi, a theropod dinosaur from the Tiaojishan Formation (Upper Jurassic, China)

Cincotta

Colaux

et al. 2020

Palaeontology

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A panel of geochemical techniques is used here to investigate the taphonomy of fossil feathers preserved in association with the skeleton of the Jurassic theropod Anchiornis huxleyi. Extant feathers were analysed in parallel to test whether the soft tissues morphologically preserved in the fossil also exhibit a high degree of chemical preservation. Scanning electron microscopy (SEM) and energy dispersive spectroscopy (EDS) indicate that clays and iron oxide pseudomorphs occur in the surrounding sediment and also reveal the preservation of melanosome‐like microbodies in the fossil. Carbon gradient along a depth profile and co‐occurrence of carbon and sulphur are shown in the fossil by elastic backscattering (EBS) and particle‐induced x‐ray emission (PIXE), which are promising techniques for the elemental analysis of fossil soft tissues. The molecular composition of modern and fossil soft tissues was assessed from micro‐attenuated total reflectance fourier transform infrared spectroscopy (micro‐ATR FTIR), solid‐state 13C nuclear magnetic resonance (CP‐MAS 13C NMR) and pyrolysis gas chromatography mass spectrometry in the presence of TMAH (TMAH‐Py‐GC‐MS). Results indicate that the proteinaceous material that comprises the modern feathers is not present in the fossil feathers. The fossil feathers and the embedding sediment exhibit a highly aliphatic character. However, substantial differences exist between these samples, revealing that the organic matter of the fossil feathers is, at least partially, derived from original constituents of the feathers. Our results suggest that, despite the morphological preservation of Anchiornis feathers, original proteins, that is keratin, were probably not preserved in the 160‐myr‐old feathers.

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Section: Resultsmentioning

confidence: 99%

“…Imidazolidinedione 12 probably results from the internal cyclization of tripeptide comprising an alanine unit as reported by Templier et al . (; Cincotta et al . , fig.…”

Section: Resultsmentioning

confidence: 99%

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Chemical preservation of tail feathers fromAnchiornis huxleyi, a theropod dinosaur from the Tiaojishan Formation (Upper Jurassic, China)

Cincotta

Colaux

et al. 2020

Palaeontology

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“…For all the tested corals, acetamide was the most abundant product of this class, followed by acetic acid. These [39,41] two compounds are both reported in the literature to be formed upon chitin pyrolysis; however, acetic acid is a common pyrolysis product obtained by several biopolymers such as wood [30] and humic matter [32], while acetamide is a typical product from pyrolysis of microbial cell walls [33] and could be formed upon pyrolysis of other precursors such as (3); mannosan (4); 1,6-anhydrogalactofuranose (5); levoglucosan (6); 1,6-anhydroglucofuranose (7); tetradecanoic (myristic) acid (8); C15 acids (9); hexadecanol (10); hexadecenoic acids (11); hexadecanoic (palmitic) acid (12); octadecen-9-ol (13); C17 acids (14); octadecanol (15); octadecenoic acid isomers (16); octadecanoic acid (17); monomyristin (18); eicosadienoic acids (19); eicosenoic acids (20); eicosanoic acid (21); monopalmitin (22); docosenoic acid (23); docosanoic (24); monostearin (25); tetracosenoic acids (26); tetracosanoic acid (27); hexacosanoic acid (28); cholestanol (29); octadocanoic (30). hexadecanoic acid, hexadecyl ester (31) thermally labile proteins [36].…”

Section: Polysaccharidesmentioning

confidence: 99%

“…This approach was already reported in the literature for determining specific amino acidic sequences of a protein fragment obtained from the alkaline digestion of abalone shell [18]. Particular attention was paid to the identification of 2,5-diketopiperazines (DKPs), since they form upon pyrolysis of peptides and proteins from the cyclization of two adjacent amino acids retaining their side chains [23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Analytical pyrolysis-based study on intra-skeletal organic matrices from Mediterranean corals

et al. 2014

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Off-line analytical pyrolysis combined with gas chromatography–mass spectroscopy (GC–MS), directly or after trimethylsilylation, along with infrared spectroscopy and amino acid analysis was applied for the first time to the characterization of the intra-skeletal organic matrix (OM) extracted from four Mediterranean hard corals. They were diverse in growth form and trophic strategy namely Balanophyllia europaea and Leptopsammia pruvoti—solitary corals, only the first having zooxanthelle—and Cladocora caespitosa and Astroides calycularis—colonial corals, only the first with zooxanthelle. Pyrolysis products evolved from OM could be assigned to lipid (e.g. fatty acids, fatty alcohols, monoacylglicerols), protein (e.g. 2,5-diketopiperazines, DKPs) and polysaccharide (e.g. anhydrosugars) precursors. Their quantitative distribution showed for all the species a low protein content with respect to lipids and polysaccharides. A chemometric approach using principal component analysis (PCA) and clustering analysis was applied on OM mean amino acidic compositions. The small compositional diversity across coral species was tentatively related with coral growth form. The presence of N-acetyl glucosamine markers suggested a functional link with other calcified tissues containing chitin. The protein fraction was further investigated using novel DKP markers tentatively identified from analytical pyrolysis of model polar linear dipeptides. Again, no correlation was observed in relation to coral ecology. These analytical results revealed that the bulk structure and composition of OMs among studied corals are similar, as it is the textural organization of the skeleton mineralized units. Therefore, they suggest that coral’s biomineralization is governed by similar macromolecules, and probably mechanisms, independently from their ecology.

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Characterizing the molecular structure of organic matter from natural environments: An analytical challenge

Derenne

2014

Comptes Rendus. Géoscience

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Analytical TMAH pyrolysis of dipeptides: Formation of new complex cyclic compounds related to the presence of the peptide bond

Cited by 7 publications

References 28 publications

Chemical preservation of tail feathers fromAnchiornis huxleyi, a theropod dinosaur from the Tiaojishan Formation (Upper Jurassic, China)

Chemical preservation of tail feathers fromAnchiornis huxleyi, a theropod dinosaur from the Tiaojishan Formation (Upper Jurassic, China)

Analytical pyrolysis-based study on intra-skeletal organic matrices from Mediterranean corals

Characterizing the molecular structure of organic matter from natural environments: An analytical challenge

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