MALDI mass spectrometry monitoring of cyclodextrin-oligolactide derivatives synthesis

Blaj, Diana-Andreea; Balan-Porcăraşu, Mihaela; Petre, Brînduşa Alina; Harabagiu, Valeria; Peptu, Cristian

doi:10.1016/j.polymer.2021.124186

Cited by 15 publications

(24 citation statements)

References 66 publications

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“…Common ring-opening polymerization (ROP) catalysts have been used to prepare well-defined star-shaped polymers by the core-first procedure—for example, tin octoate [ 12 , 13 , 14 , 15 , 16 ] or various amines such as 4-dimethylaminopyridine (DMAP) for lactide [ 17 , 18 , 19 ] and (–)-sparteine (SP) for β-butyrolactone [ 20 , 21 ]. Organometallic catalysts have also been successfully used for the CD-initiated ROP of ε-caprolactone (ε-CL) [ 22 , 23 ], L -lactide [ 24 ], lactones, and carbonates [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

“…However, lactide bulk polymerization, only in the presence of CD, leads to multiple esterifications, selectively at primary hydroxyl groups of CD [ 45 ]. Moreover, the modification of CD also takes place at the primary hydroxyl groups, under the conditions of solution ring-opening oligomerization of lactides [ 19 , 46 , 47 ].…”

Section: Introductionmentioning

confidence: 99%

“…MALDI MS represents a powerful technique for the characterization of complex chemical structures, allowing the identification of monomer units and end chain groups, and the precise determination of the average molecular weights of polymer samples with narrow dispersity [ 49 , 50 ]. Moreover, MALDI MS may be employed for witnessing minute changes in molecular weights during polymerization reactions—thus expanding its use, as shown by previous studies concerning the ring-opening polymerization (ROP) of lactide [ 19 , 51 , 52 ]. MALDI MS has already been employed for the in-depth structural characterization of cyclodextrin-oligoester derivatives [ 17 , 19 , 25 , 42 , 46 , 48 ].…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, MALDI MS may be employed for witnessing minute changes in molecular weights during polymerization reactions—thus expanding its use, as shown by previous studies concerning the ring-opening polymerization (ROP) of lactide [ 19 , 51 , 52 ]. MALDI MS has already been employed for the in-depth structural characterization of cyclodextrin-oligoester derivatives [ 17 , 19 , 25 , 42 , 46 , 48 ]. More specifically, MALDI mass spectrometry has previously proven its utility in studying the reaction kinetics of the ring-opening polymerization of lactide, showing an excellent agreement with SEC and 1 H NMR [ 19 , 51 ].…”

Section: Introductionmentioning

confidence: 99%

“…MALDI MS has already been employed for the in-depth structural characterization of cyclodextrin-oligoester derivatives [ 17 , 19 , 25 , 42 , 46 , 48 ]. More specifically, MALDI mass spectrometry has previously proven its utility in studying the reaction kinetics of the ring-opening polymerization of lactide, showing an excellent agreement with SEC and 1 H NMR [ 19 , 51 ].…”

Section: Introductionmentioning

confidence: 99%

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Cyclodextrin-Oligocaprolactone Derivatives—Synthesis and Advanced Structural Characterization by MALDI Mass Spectrometry

Peptu¹,

Blaj²,

Balan-Porcăraşu³

et al. 2022

Polymers

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Cyclodextrins have previously been proven to be active in the catalysis of cyclic ester ring-opening reactions, hypothetically in a similar way to lipase-catalyzed reactions. However, the way they act remains unclear. Here, we focus on β-cyclodextrin’s involvement in the synthesis and characterization of β-cyclodextrin-oligocaprolactone (CDCL) products obtained via the organo-catalyzed ring-opening of ε-caprolactone. Previously, bulk or supercritical carbon dioxide polymerizations has led to inhomogeneous products. Our approach consists of solution polymerization (dimethyl sulfoxide and dimethylformamide) to obtain homogeneous CDCL derivatives with four monomer units on average. Oligomerization kinetics, performed by a matrix-assisted laser desorption ionization mass spectrometry (MALDI MS) optimized method in tandem with 1H NMR, revealed that monomer conversion occurs in two stages: first, the monomer is rapidly attached to the secondary OH groups of β-cyclodextrin and, secondly, the monomer conversion is slower with attachment to the primary OH groups. MALDI MS was further employed for the measurement of the ring-opening kinetics to establish the influence of the solvents as well as the effect of organocatalysts (4-dimethylaminopyridine and (–)-sparteine). Additionally, the mass spectrometry structural evaluation was further enhanced by fragmentation studies which confirmed the attachment of oligoesters to the cyclodextrin and the cleavage of dimethylformamide amide bonds during the ring-opening process.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Cyclodextrin-Oligocaprolactone Derivatives—Synthesis and Advanced Structural Characterization by MALDI Mass Spectrometry

Peptu¹,

Blaj²,

Balan-Porcăraşu³

et al. 2022

Polymers

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Investigations into the characterization, degradation, and applications of biodegradable polymers by mass spectrometry

Rizzarelli,

Leanza,

Rapisarda

2023

Mass Spectrometry Reviews

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Biodegradable polymers have been getting more and more attention because of their contribution to the plastic pollution environmental issues and to move towards a circular economy. Nevertheless, biodegradable materials still exhibit various disadvantages restraining a widespread use in the market. Therefore, additional research efforts are required to improve their performance. Mass spectrometry (MS) affords a relevant contribution to optimize biodegradable polymer synthesis, to confirm macromolecular structures, to examine along the time the progress of degradation processes and highlight advantages and drawbacks in the extensive applications. This review aims to provide an overview of the MS investigations carried out to support the synthesis of biodegradable polymers, with helpful information on undesirable products or polymerization mechanism, to understand deterioration pathways by the structure of degradation products and to follow drug release and pharmacokinetic. Additionally, it summarizes MS studies addressed on environmental and health issues related to the extensive use of plastic materials, that is, potential migration of additives or microplastics identification and quantification. The paper is focused on the most significant studies relating to synthetic and microbial biodegradable polymers published in the last 15 years, not including agro‐polymers such as proteins and polysaccharides.

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2021–2022

Harvey

2024

Mass Spectrometry Reviews

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The use of matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of carbohydrates and glycoconjugates is a well‐established technique and this review is the 12th update of the original article published in 1999 and brings coverage of the literature to the end of 2022. As with previous review, this review also includes a few papers that describe methods appropriate to analysis by MALDI, such as sample preparation, even though the ionization method is not MALDI. The review follows the same format as previous reviews. It is divided into three sections: (1) general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation, quantification and the use of computer software for structural identification. (2) Applications to various structural types such as oligo‐ and polysaccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals, and (3) other general areas such as medicine, industrial processes, natural products and glycan synthesis where MALDI is extensively used. Much of the material relating to applications is presented in tabular form. MALDI is still an ideal technique for carbohydrate analysis, particularly in its ability to produce single ions from each analyte and advancements in the technique and range of applications show little sign of diminishing.

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MALDI mass spectrometry monitoring of cyclodextrin-oligolactide derivatives synthesis

Cited by 15 publications

References 66 publications

Cyclodextrin-Oligocaprolactone Derivatives—Synthesis and Advanced Structural Characterization by MALDI Mass Spectrometry

Cyclodextrin-Oligocaprolactone Derivatives—Synthesis and Advanced Structural Characterization by MALDI Mass Spectrometry

Investigations into the characterization, degradation, and applications of biodegradable polymers by mass spectrometry

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2021–2022

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