Transferring the biorenewable nitrogen present in chitin to several N-functional groups

Pham, Thuy Trang; Lindsay, Ashley C.; Chen, Xi; Gözaydın, Gökalp; Yan, Ning; Sperry, Jonathan

doi:10.1016/j.scp.2019.100143

Cited by 21 publications

(26 citation statements)

References 71 publications

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“…While the preparation and use of the two furan derivatives 5-HMF and 3A5AF has been studied actively in recent years, 8,[10][11][12][13][14] the furanyl diol dihydroxyethyl acetamidofuran (Di-HAF) attracted less attention. This bis-dehydration product of GlcNAc was identified by Kuhn and Krüger in 1956 15 as an intermediate in the Morgan-Elson method for quantitative determination of hexosamines 16 and was named chromogen III.…”

Section: Introductionmentioning

confidence: 99%

“…18 In addition to the chiral center, the acetamido group of GlcNAc also remains present and therefore Di-HAF is a socalled Haber-independent nitrogen-containing compound. 12 Nitrogen containing compounds are omnipresent in pharmaceuticals, textiles, soaps and surfactants, 4 and the vast majority of the nitrogen in these compounds comes from ammonia produced in the Haber-Bosch process. 12 This process is notoriously energy inefficient and utilizing a biorenewable source would be a more sustainable and energy efficient alternative.…”

Section: Introductionmentioning

confidence: 99%

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The dehydration of N-acetylglucosamine (GlcNAc) to enantiopure dihydroxyethyl acetamidofuran (Di-HAF)

et al. 2021

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The dehydration of N-acetylglucosamine (GlcNAc) to enantiopure dihydroxyethyl acetamidofuran (Di-HAF)

et al. 2021

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“…The interest in these molecules has been growing along with environmental concerns [ 159 ]. Some examples of biopolymers are: cellulose, the most abundant one in nature; chitosan, a versatile polymer attainable by treating chitin from the crustacean shell waste generated by the seafood industry; and lignin, a byproduct of the paper industry with great qualities, including antioxidant activity and high thermal stability [ 158 , 159 , 160 , 161 ]. Recent studies with hydroxypropyl methylcellulose (HPMC)/lignin and HPMC/lignin/chitosan films had positive results, with antimicrobial effect against both Gram−positive and Gram−negative at 35 and 0–7 °C [ 158 ].…”

Section: Asas With Apsmentioning

confidence: 99%

Antimicrobial Polymer−Based Assemblies: A Review

Carmona-Ribeiro

Araújo

2021

IJMS

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An antimicrobial supramolecular assembly (ASA) is conspicuous in biomedical applications. Among the alternatives to overcome microbial resistance to antibiotics and drugs, ASAs, including antimicrobial peptides (AMPs) and polymers (APs), provide formulations with optimal antimicrobial activity and acceptable toxicity. AMPs and APs have been delivered by a variety of carriers such as nanoparticles, coatings, multilayers, hydrogels, liposomes, nanodisks, lyotropic lipid phases, nanostructured lipid carriers, etc. They have similar mechanisms of action involving adsorption to the cell wall, penetration across the cell membrane, and microbe lysis. APs, however, offer the advantage of cheap synthetic procedures, chemical stability, and improved adsorption (due to multipoint attachment to microbes), as compared to the expensive synthetic routes, poor yield, and subpar in vivo stability seen in AMPs. We review recent advances in polymer−based antimicrobial assemblies involving AMPs and APs.

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“…Chitin is considered as the most promising biomass sources for the production of renewable N-containing chemicals and materials due to its high nitrogen content of around 7% by weight. (Omari et al, 2012;Chen et al, 2014;Chen et al, 2017;Kobayashi et al, 2017Kobayashi et al, , 2019Osada et al, 2019;Pham et al, 2019;Dai et al, 2020). In spite of the enormous economic and environmental interests, the existence of acetyl groups is the main challenge for the exploitation of chitin biomass, which seriously hampers its transformation into fuels and fine chemicals (Fang and Fan et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

Selective Utilization of N-acetyl Groups in Chitin for Transamidation of Amines

Shen

Liu

et al. 2021

Front. Chem. Eng.

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The selective transformation of chitin into various renewable N-containing chemicals and medicines has attracted increasing attention. However, the N-acetyl groups in chitin construct strong hydrogen bond networks, which restricts its depolymerization and transformation. The selective conversion of robust chitin commonly requires considerable base catalysts to remove the N-acetyl group as a byproduct in advance, which is non-compliance with the principle of atomic economy. Herein, for the first time we demonstrate a novel approach to achieve the selective utilization of the N-acetyl group in chitin for transamidation of chitin with amines. A series of amine derivatives, mainly including aliphatic amine, cyclic amine and functionalized aromatic amine, could be selectively converted into the corresponding amide products frequently found in pharmaceuticals. Furthermore, the solid residue after removing the acetyl group (denoted as De-chitin) with the sufficient exposure of -NH2 groups as a solid base catalyst shows excellent performance in the aldol condensation reaction of furfural and acetone to produce fuel precursors. Our process provides a strategy that exploiting every functional group adequately in substrates to obtain value-added chemicals.

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Transferring the biorenewable nitrogen present in chitin to several N-functional groups

Cited by 21 publications

References 71 publications

The dehydration of N-acetylglucosamine (GlcNAc) to enantiopure dihydroxyethyl acetamidofuran (Di-HAF)

The dehydration of N-acetylglucosamine (GlcNAc) to enantiopure dihydroxyethyl acetamidofuran (Di-HAF)

Antimicrobial Polymer−Based Assemblies: A Review

Selective Utilization of N-acetyl Groups in Chitin for Transamidation of Amines

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