Efficient heterogeneous synthesis of reactive polygalacturonic acid hydrazides

Würfel, Hendryk; Geitel, Katja; Heinze, Thomas

doi:10.1016/j.carbpol.2021.117838

Cited by 8 publications

(9 citation statements)

References 15 publications

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“…[ 5 ] On the contrary, the nucleophilic polygalacturonic acid hydrazide (PGH) is easily available in a one‐step heterogeneous protocol with simple purification even by a large‐scale procedure. [ 3 ] To study the nucleophilic nature of PGH toward aldehydes and to get all‐sugar‐based products, it was allowed to react with D ‐glucose in water under homogeneous reaction conditions ( Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…The starting material PGH was tested with hen's egg test and showed to be non‐toxic. [ 3 ] The same can be assumed for the products formed. In the first step, glucose is added to the aqueous solution of PGH only.…”

Section: Resultsmentioning

confidence: 99%

“…Materials: PGH was synthesized by heterogeneous conversion of the polygalacturonic acid with hydrazine hydrate according to literature. [3] Hydrazine hydrate (80 w%) was obtained from Merck, D-glucose (≥99.5 %), and D-glucose-13 C 6 (≥99.0 %) from Sigma-Aldrich. Polygalacturonic acid (Sigma-Aldrich) had a content of galacturonic acid ≥90 % (enzymatic) and M n = 56 900 g mol −1 , determined by SEC corresponding to a degree of polymerization (DP) = 330.…”

Section: Methodsmentioning

confidence: 99%

“…The PS hydrazides formed were shown to be nontoxic, well water‐soluble, and storage‐stable biopolymer derivatives. [ 3 ] Hence, platform compounds for the design of new bio‐based materials became accessible, showing reactivity concerning multivalent metal ions and carbonyl group‐containing molecules, including aldehydes and ketones.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Glucose Scavenging with Pectin Hydrazide: A Step toward Designing Innovative, Functional, All‐Sugar‐Based Polymers

Würfel

Geitel

Günther

et al. 2022

Macro Chemistry & Physics

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Polygalacturonic acid hydrazide (PGH) is one of only a few polysaccharide derivatives with pronounced nucleophilic characteristics known today. This water-soluble and benign material could be reacted with the hydrophilic aldehydes D-glucose in water, without any catalyst and at room temperature, resulting in a product that is the first example of new family of all-sugar-based polysaccharide derivatives. The reaction is reversible, allowing for D-glucose loading and unloading of the PGH. The D-glucose binds as the 𝜶−, and 𝜷 anomer of the glucopyranosyl form. The reaction is orthogonal to the reactivity of the hydroxyl groups in the polysaccharide and enables the mild generation of new bio-inspired polysaccharide derivatives. The glucose attachment could be rendered irreversibly by reducing the hydrazone with sodium cyanoborohydride, leading to the acyclic sugar derivative. A brief hydrodynamic and light scattering study of the polymers showed varying macromolecular properties at consistent molar mass values of the modified polysaccharide derivatives.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Glucose Scavenging with Pectin Hydrazide: A Step toward Designing Innovative, Functional, All‐Sugar‐Based Polymers

Würfel

Geitel

Günther

et al. 2022

Macro Chemistry & Physics

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“…Scheme 11. Homogeneous reaction of high-methoxy pectin with hydrazine hydrate in water at elevated temperatures A heterogeneous synthesis approach for pectin hydrazide could be realized as well and was shown to be more efficient and even useful for industrial application (Würfel et al 2021). The reaction of LMP or PGA proceeds in a slurry of 2-propanol between RT and 50 °C, applying 4 eq.…”

Section: Formation Of Hydrazidementioning

confidence: 99%

Chemical modification of pectin and polygalacturonic acid: A critical review

Würfel

Geitel

et al. 2021

BioRes

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Pectin, as a sustainable biopolymer with its two complementary functionalities (carboxyl and hydroxyl moieties) imparted in the α-1,4-galacturonic acid repeating unit, has gained increasing attention in the last few years. The interest in this ubiquitously occurring plant originating polysaccharide (PS) has shifted slowly from applications as a food additive to a broader range of potential applications in medicine, cosmetics, and other industries. Due to the increasing interest in alternatives for petrochemical materials, PSs as biomaterials have gained increasing attention in industrial processes in general. In the last decade, an increasing number of chemical transformations related to pectin have been published, and this is a prerequisite for the design of the structure and hence properties of novel biopolymer-based materials. This work aims to review the chemical modifications of pectin by covalent linkage of the last decade and analyze the materials obtained with these chemical methods critically.

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Efficient heterogeneous synthesis of nucleophilic carboxymethyl hydrazides of polysaccharides

Würfel,

Pfeifer,

Heinze

2024

Biopolymers

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Nucleophilic moieties in polysaccharides (PS) with distinct higher reactivity compared with the hydroxy group are interesting for sustainable applications in chemistry, medicine, and pharmacy. An efficient heterogeneous method for the formation of such nucleophilic PS is described. Employing alcohols as slurry medium, protonated carboxymethyl (CM) PS and hydrazine hydrate are allowed to react at elevated temperatures. The CM derivatives of starch and pullulan can be transformed almost quantitatively to the corresponding hydrazides. The reaction is less efficient for CM dextrans and CM xylans. As slurry media, 2‐propanol and ethanol were probed, and the results are compared with a homogeneous procedure performed in water. Overall, the heterogeneous procedure is superior compared with the homogeneous route. 2‐Propanol is the best slurry medium investigated yielding PS hydrazides with the highest nitrogen content.

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Efficient heterogeneous synthesis of reactive polygalacturonic acid hydrazides

Cited by 8 publications

References 15 publications

Glucose Scavenging with Pectin Hydrazide: A Step toward Designing Innovative, Functional, All‐Sugar‐Based Polymers

Glucose Scavenging with Pectin Hydrazide: A Step toward Designing Innovative, Functional, All‐Sugar‐Based Polymers

Chemical modification of pectin and polygalacturonic acid: A critical review

Efficient heterogeneous synthesis of nucleophilic carboxymethyl hydrazides of polysaccharides

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