Quantitative protection of chitin by one-step tritylation and benzylation to synthesize precursors for chemical modifications

Umemura, Tohru; Hirakawa, Masaaki; Yoshida, Yuhya; Kurita, Keisuke

doi:10.1007/s00289-012-0719-9

“…The benzylation of chitin was reported [21]. β -Chitin was suspended in DMSO, and sodium hydride (5 equiv.)…”

Section: Saccharide Oxygen As Nucleophilementioning

confidence: 99%

“…Amylose underwent tritylation regioselectively at O-6 uneventfully [52]. Chitin was also tritylated regioselectivity with reaction at O-6 [21]. β -Chitin was suspended in pyridine and heated at 90°C for 72 h with trityl chloride (10 equiv.)…”

Section: Saccharide Oxygen As Nucleophilementioning

confidence: 99%

Chemical Modification of Polysaccharides

Cumpstey¹

2013

ISRN Organic Chemistry

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This review covers methods for modifying the structures of polysaccharides. The introduction of hydrophobic, acidic, basic, or other functionality into polysaccharide structures can alter the properties of materials based on these substances. The development of chemical methods to achieve this aim is an ongoing area of research that is expected to become more important as the emphasis on using renewable starting materials and sustainable processes increases in the future. The methods covered in this review include ester and ether formation using saccharide oxygen nucleophiles, including enzymatic reactions and aspects of regioselectivity; the introduction of heteroatomic nucleophiles into polysaccharide chains; the oxidation of polysaccharides, including oxidative glycol cleavage, chemical oxidation of primary alcohols to carboxylic acids, and enzymatic oxidation of primary alcohols to aldehydes; reactions of uronic-acid-based polysaccharides; nucleophilic reactions of the amines of chitosan; and the formation of unsaturated polysaccharide derivatives.

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“…The resulting fully protected products were selectively deprotected to afford the corresponding products . Interestingly, it was observed that the chitin type (α or β) influences some chemical modifications …”

Section: Selective Modificationmentioning

confidence: 99%

“…Umemura et al. verified that the functionalization of hydroxyl groups of squid β‐chitin with trityl or benzyl groups proceeded more easily than those of shrimp α‐chitin . Although, for α‐chitin, the 6‐ O ‐trityl derivative was prepared from the trimethylsilylated chitin, the β‐chitin exhibited higher reactivity and direct O‐6 tritylation was achieved in a quantitative way.…”

Section: Selective Modificationmentioning

confidence: 99%

Selective Modification of Chitin and Chitosan: En Route to Tailored Oligosaccharides

Carvalho

¹

,

Queda

²

,

Santos

³

et al. 2016

Chemistry An Asian Journal

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Chitin and chitosan are attractive biopolymers with enormous structural possibilities for chemical modification, creating platforms for new chemical entities with a broad scope of applications, ranging from material science to medicine. During the last few years, incredible efforts have been dedicated to the regioselective modification of these biopolymers paving the way for improved properties and tailored activities. Herein, the most recent advances in chitin/chitosan regioselective modification, reaction conditions, selectivity, and the impact on its applications are highlighted. Moreover, the recent focus on chitooligosaccharides, their regioselective and chemoselective functionalization, as well as their role in biological studies, including molecular recognition with several biological targets are also covered.

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“…The benzylation of chitin was reported [21]. -Chitin was suspended in DMSO, and sodium hydride (5 equiv.)…”

Section: Alkyl and Benzyl Ethersmentioning

confidence: 99%

Modication of Heterocyclic Amino Acids: Histidine and Tryptophan

2016

Chemical Modification of Biological Polymers

0

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This review covers methods for modifying the structures of polysaccharides. The introduction of hydrophobic, acidic, basic, or other functionality into polysaccharide structures can alter the properties of materials based on these substances. The development of chemical methods to achieve this aim is an ongoing area of research that is expected to become more important as the emphasis on using renewable starting materials and sustainable processes increases in the future. The methods covered in this review include ester and ether formation using saccharide oxygen nucleophiles, including enzymatic reactions and aspects of regioselectivity; the introduction of heteroatomic nucleophiles into polysaccharide chains; the oxidation of polysaccharides, including oxidative glycol cleavage, chemical oxidation of primary alcohols to carboxylic acids, and enzymatic oxidation of primary alcohols to aldehydes; reactions of uronic-acid-based polysaccharides; nucleophilic reactions of the amines of chitosan; and the formation of unsaturated polysaccharide derivatives.

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Quantitative protection of chitin by one-step tritylation and benzylation to synthesize precursors for chemical modifications

Cited by 7 publications

References 23 publications

Chemical Modification of Polysaccharides

Chemical Modification of Polysaccharides

Selective Modification of Chitin and Chitosan: En Route to Tailored Oligosaccharides

Modication of Heterocyclic Amino Acids: Histidine and Tryptophan

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Quantitative protection of chitin by one-step tritylation and benzylation to synthesize precursors for chemical modifications

Cited by 7 publications

References 23 publications

Chemical Modification of Polysaccharides

Chemical Modification of Polysaccharides

Selective Modification of Chitin and Chitosan: En Route to Tailored Oligosaccharides

Modication of Heterocyclic Amino Acids: Histidine and Tryptophan

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Product

Resources

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Modication of Heterocyclic Amino Acids: Histidine and Tryptophan