Chemo-enzymatic protocol converts chitin into a nitrogen-containing furan derivative, 3-acetamido-5-acetylfuran

Chen, Kequan; Wu, Chao; Wang, Chengyong; Zhang, Alei; Cao, Fei; Ouyang, Pingkai

doi:10.1016/j.mcat.2021.112001

Cited by 10 publications

(11 citation statements)

References 34 publications

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“…The same group [58] found that ball mill treatment without additives was beneficial to the destruction of the hydrogen-bond network and crystalline region, which significantly enhanced the reactivity of chitin and gave a 29 mol% yield of 3A5AF in [BMIm]Cl. Very recently, Chen et al [59] demonstrated a novel chemo-enzymatic protocol for the transformation of chitin to 3A5AF, as shown in Scheme 6. Unlike previous investigations [56][57][58], chitin was nearly 100% converted into GlcNAc over the recyclable chitinolytic enzyme.…”

Section: Chitin As Reactantmentioning

confidence: 99%

Progress in Catalytic Conversion of Renewable Chitin Biomass to Furan-Derived Platform Compounds

Dai

et al. 2022

Catalysts

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Chitin is one of the most abundant biopolymers on Earth but under-utilized. The effective conversion of chitin biomass to useful chemicals is a promising strategy to make full use of chitin. Among chitin-derived compounds, some furan derivatives, typically 5-hydroxymethylfurfural and 3-acetamido-5-acetylfuran, have shown great potential as platform compounds in future industries. In this review, different catalytic systems for the synthesis of nitrogen-free 5-hydroxymethylfurfural and nitrogen-containing 3-acetamido-5-acetylfuran from chitin or its derivatives are summarized comparatively. Some efficient technologies for enhancing chitin biomass conversion have been introduced. Last but not least, future challenges are discussed to enable the production of valuable compounds from chitin biomass via greener processes.

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Section: Chitin As Reactantmentioning

confidence: 99%

Progress in Catalytic Conversion of Renewable Chitin Biomass to Furan-Derived Platform Compounds

Dai

et al. 2022

Catalysts

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“…Purification of 3A5AF often requires column chromatography, although Zhang and co‐workers reported obtaining 3A5AF needle shape crystals in methanol/H 2 O solution [27d] . We designed an approach to get 3AF crystals through extraction‐decoloration‐crystallization (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

“…This is the reason that 3AF synthesis from NAG has not been reported. To increase the yield of 3AF, various catalytic promoters that have been reported for 3A5AF synthesis such as thiourea, [27d] ionic liquid, [27c] choline chloride, [31] and NaOH, [27a] were added in the H 3 BO 3 −NaCl system. Addition of thiourea, ionic liquid, or choline chloride the did not efficiently improved the yield of 3AF (Table S1); however, yields increasing from 3.5 % to 29.9 % could be achieved when NaOH was added.…”

Section: Resultsmentioning

confidence: 99%

Biomass to Aromatic Amine Module: Alkali Catalytic Conversion of N‐Acetylglucosamine into Unsubstituted 3‐Acetamidofuran by Retro‐Aldol Condensation

et al. 2023

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Aminofurans are widely used in drug synthesis as aromatic modules analogous to aniline. However, unsubstituted aminofuran compounds are difficult to prepare. In this study, a process for the selective conversion of N‐acetyl‐d‐glucosamine (NAG) into unsubstituted 3‐acetamidofuran (3AF) is developed. The yield of 3AF from NAG catalyzed by a ternary Ba(OH)2−H3BO3−NaCl catalytic system in N‐methylpyrrolidone at 180 °C for 20 min can reach 73.9 %. Mechanistic studies reveal that the pathway to 3AF starts with a base‐promoted retro‐aldol condensation of the ring‐opened NAG, affording the key intermediate N‐acetylerythrosamine. Judicious selection of the catalyst system and conditions enables the selective conversion of biomass‐derived NAG into 3AF or 3‐acetamido‐5‐acetylfuran.

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“…used chitinolytic enzyme and NH 4 SCN to directly catalyze the reaction of chitin with the addition of cocatalyst CaCl 2 in DMA obtained 56.66% of 3A5AF. 34 Although, ionic liquids have excellent performance for the GlcNAc biorefinery reactions, their tedious preparation process, high cost, and difficulty in storage limit large-scale applications. The conversion of GlcNAc by enzyme-chemical and high temperature water method is more complicated and higher requirements for equipment.…”

Section: Introductionmentioning

confidence: 99%

Switchable product selectivity in dehydration of N-acetyl-d-glucosamine promoted by choline chloride-based deep eutectic solvents

et al. 2023

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Chemo-enzymatic protocol converts chitin into a nitrogen-containing furan derivative, 3-acetamido-5-acetylfuran

Cited by 10 publications

References 34 publications

Progress in Catalytic Conversion of Renewable Chitin Biomass to Furan-Derived Platform Compounds

Progress in Catalytic Conversion of Renewable Chitin Biomass to Furan-Derived Platform Compounds

Biomass to Aromatic Amine Module: Alkali Catalytic Conversion of N‐Acetylglucosamine into Unsubstituted 3‐Acetamidofuran by Retro‐Aldol Condensation

Switchable product selectivity in dehydration of N-acetyl-d-glucosamine promoted by choline chloride-based deep eutectic solvents

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