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Sequencing Biodegradable and Potentially Biobased Polyesteramide of Sebacic Acid and 3-Amino-1-propanol by MALDI TOF-TOF Tandem Mass Spectrometry.
Polymers (Basel). 2022 Apr 07; 14(8)P

Abstract

Biodegradable and potentially biobased polyesteramide oligomers (PEA-Pro), obtained from melt condensation of sebacic acid and 3-amino-1-propanol, were characterized by nuclear magnetic resonance (NMR), matrix assisted laser desorption/ionization-time of flight/time of flight-mass spectrometry/mass spectrometry (MALDI-TOF/TOF-MS/MS), thermogravimetric analysis (TGA), and pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS). NMR analysis showed the presence of hydroxyl and amino terminal groups as well as carboxylic groups of the sebacate moiety. Hydroxyl and carboxyl termination had the same abundance, while the amine termination was 2.7-times less frequent. Information regarding the fragmentation pathways and ester/amide bond sequences was obtained by MALDI-TOF/TOF-MS/MS analysis performed on sodiated adducts of cyclic species and linear oligomers. Different end groups did not influence the observed fragmentation. Three fragmentation pathways were recognized. The β-hydrogen-transfer rearrangement, which leads to the selective scission of the -O-CH2- bonds, was the main mechanism. Abundant product ions originating from -CH2-CH2- (β-γ) bond cleavage in the sebacate moiety and less abundant ions formed by -O-CO- cleavages were also detected. TGA showed a major weight loss (74%) at 381 °C and a second degradation step (22% weight loss) at 447 °C. Py-GC/MS performed in the temperature range of 350-400 °C displayed partial similarity between the degradation products and the main fragments detected in the MALDI-TOF/TOF-MS/MS experiments. Degradation products derived from amide bonds were related to the formation of CN groups, in agreement with the literature.

Authors+Show Affiliations

Istituto per i Polimeri, Compositi e Biomateriali, Consiglio Nazionale delle Ricerche, Via Paolo Gaifami 18, 95126 Catania, Italy.STMicroelectronics Srl, Stradale Primosole, 50, 95121 Catania, Italy.Istituto per i Polimeri, Compositi e Biomateriali, Consiglio Nazionale delle Ricerche, Via Paolo Gaifami 18, 95126 Catania, Italy.Istituto per i Polimeri, Compositi e Biomateriali, Consiglio Nazionale delle Ricerche, Via Paolo Gaifami 18, 95126 Catania, Italy.Istituto per i Polimeri, Compositi e Biomateriali, Consiglio Nazionale delle Ricerche, Via Paolo Gaifami 18, 95126 Catania, Italy.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

35458250

Citation

Rizzarelli, Paola, et al. "Sequencing Biodegradable and Potentially Biobased Polyesteramide of Sebacic Acid and 3-Amino-1-propanol By MALDI TOF-TOF Tandem Mass Spectrometry." Polymers, vol. 14, no. 8, 2022.
Rizzarelli P, La Carta S, Mirabella EF, et al. Sequencing Biodegradable and Potentially Biobased Polyesteramide of Sebacic Acid and 3-Amino-1-propanol by MALDI TOF-TOF Tandem Mass Spectrometry. Polymers (Basel). 2022;14(8).
Rizzarelli, P., La Carta, S., Mirabella, E. F., Rapisarda, M., & Impallomeni, G. (2022). Sequencing Biodegradable and Potentially Biobased Polyesteramide of Sebacic Acid and 3-Amino-1-propanol by MALDI TOF-TOF Tandem Mass Spectrometry. Polymers, 14(8). https://doi.org/10.3390/polym14081500
Rizzarelli P, et al. Sequencing Biodegradable and Potentially Biobased Polyesteramide of Sebacic Acid and 3-Amino-1-propanol By MALDI TOF-TOF Tandem Mass Spectrometry. Polymers (Basel). 2022 Apr 7;14(8) PubMed PMID: 35458250.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Sequencing Biodegradable and Potentially Biobased Polyesteramide of Sebacic Acid and 3-Amino-1-propanol by MALDI TOF-TOF Tandem Mass Spectrometry. AU - Rizzarelli,Paola, AU - La Carta,Stefania, AU - Mirabella,Emanuele Francesco, AU - Rapisarda,Marco, AU - Impallomeni,Giuseppe, Y1 - 2022/04/07/ PY - 2022/03/15/received PY - 2022/04/04/revised PY - 2022/04/05/accepted PY - 2022/4/23/entrez PY - 2022/4/24/pubmed PY - 2022/4/24/medline KW - MALDI KW - Py-GC/MS KW - biobased polymers KW - biodegradable polymers KW - characterization KW - mass spectrometry KW - polyesteramides KW - sequencing KW - tandem mass spectrometry JF - Polymers JO - Polymers (Basel) VL - 14 IS - 8 N2 - Biodegradable and potentially biobased polyesteramide oligomers (PEA-Pro), obtained from melt condensation of sebacic acid and 3-amino-1-propanol, were characterized by nuclear magnetic resonance (NMR), matrix assisted laser desorption/ionization-time of flight/time of flight-mass spectrometry/mass spectrometry (MALDI-TOF/TOF-MS/MS), thermogravimetric analysis (TGA), and pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS). NMR analysis showed the presence of hydroxyl and amino terminal groups as well as carboxylic groups of the sebacate moiety. Hydroxyl and carboxyl termination had the same abundance, while the amine termination was 2.7-times less frequent. Information regarding the fragmentation pathways and ester/amide bond sequences was obtained by MALDI-TOF/TOF-MS/MS analysis performed on sodiated adducts of cyclic species and linear oligomers. Different end groups did not influence the observed fragmentation. Three fragmentation pathways were recognized. The β-hydrogen-transfer rearrangement, which leads to the selective scission of the -O-CH2- bonds, was the main mechanism. Abundant product ions originating from -CH2-CH2- (β-γ) bond cleavage in the sebacate moiety and less abundant ions formed by -O-CO- cleavages were also detected. TGA showed a major weight loss (74%) at 381 °C and a second degradation step (22% weight loss) at 447 °C. Py-GC/MS performed in the temperature range of 350-400 °C displayed partial similarity between the degradation products and the main fragments detected in the MALDI-TOF/TOF-MS/MS experiments. Degradation products derived from amide bonds were related to the formation of CN groups, in agreement with the literature. SN - 2073-4360 UR - https://www.unboundmedicine.com/medline/citation/35458250/Sequencing_Biodegradable_and_Potentially_Biobased_Polyesteramide_of_Sebacic_Acid_and_3_Amino_1_propanol_by_MALDI_TOF_TOF_Tandem_Mass_Spectrometry_ L2 - https://www.mdpi.com/resolver?pii=polym14081500 DB - PRIME DP - Unbound Medicine ER -
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