Synthesis of chitotetraose and chitohexaose based on dimethylmaleoyl protection

Aly, Moustafa H.; Ibrahim, El‐Sayed I.; Ashry, El Sayed H. El; Schmidt, Richard R.

doi:10.1016/s0008-6215(01)00024-6

Cited by 41 publications

(10 citation statements)

References 16 publications

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“…Aly et al . [126] reported a method for synthesis of fully N- acetylated CHOS from GlcN monomers using dimethylmaleoyl as an amino protective group for synthesis of chitotetraose and chitohexaose. Removal of the amino protective group and N -acetylation was performed in a one-pot reaction to give the desired products [127].…”

Section: Chos Production—chemical Methodsmentioning

confidence: 99%

Production of Chitooligosaccharides and Their Potential Applications in Medicine

et al. 2010

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Chitooligosaccharides (CHOS) are homo- or heterooligomers of N-acetylglucosamine and D-glucosamine. CHOS can be produced using chitin or chitosan as a starting material, using enzymatic conversions, chemical methods or combinations thereof. Production of well-defined CHOS-mixtures, or even pure CHOS, is of great interest since these oligosaccharides are thought to have several interesting bioactivities. Understanding the mechanisms underlying these bioactivities is of major importance. However, so far in-depth knowledge on the mode-of-action of CHOS is scarce, one major reason being that most published studies are done with badly characterized heterogeneous mixtures of CHOS. Production of CHOS that are well-defined in terms of length, degree of N-acetylation, and sequence is not straightforward. Here we provide an overview of techniques that may be used to produce and characterize reasonably well-defined CHOS fractions. We also present possible medical applications of CHOS, including tumor growth inhibition and inhibition of TH2-induced inflammation in asthma, as well as use as a bone-strengthener in osteoporosis, a vector for gene delivery, an antibacterial agent, an antifungal agent, an anti-malaria agent, or a hemostatic agent in wound-dressings. By using well-defined CHOS-mixtures it will become possible to obtain a better understanding of the mechanisms underlying these bioactivities.

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Section: Chos Production—chemical Methodsmentioning

confidence: 99%

Production of Chitooligosaccharides and Their Potential Applications in Medicine

et al. 2010

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“…Kuyama et al (1993) performed the synthesis of fully deacetylated COS DP 20 starting with GlcN monomers using phthalimido as the amino protective group. A method for the synthesis of fully N-acetylated COS from GlcN monomers using dimethylmaleoyl as an amino protective group and subsequent N-acetylation by removing protective group for the synthesis of chitotetraose and chitohexaose was developed (Aly et al, 2001). Barroca-Aubry et al (2010) described a modular approach for the synthesis of the four different COS disaccharides, which has the potential to be elaborated into a method for the synthesis of longer chain COS with fully defined architecture.…”

Section: Cos Production By Oligomerizationmentioning

confidence: 99%

Biotechnological approaches for field applications of chitooligosaccharides (COS) to induce innate immunity in plants

Das

Madhuprakash

Sarma

et al. 2013

Critical Reviews in Biotechnology

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Plants have evolved mechanisms to recognize a wide range of pathogen-derived molecules and to express induced resistance against pathogen attack. Exploitation of induced resistance, by application of novel bioactive elicitors, is an attractive alternative for crop protection. Chitooligosaccharide (COS) elicitors, released during plant fungal interactions, induce plant defenses upon recognition. Detailed analyses of structure/function relationships of bioactive chitosans as well as recent progress towards understanding the mechanism of COS sensing in plants through the identification and characterization of their cognate receptors have generated fresh impetus for approaches that would induce innate immunity in plants. These progresses combined with the application of chitin/chitosan/COS in disease management are reviewed here. In considering the field application of COS, however, efficient and large-scale production of desired COS is a challenging task. The available methods, including chemical or enzymatic hydrolysis and chemical or biotechnological synthesis to produce COS, are also reviewed.

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“…It is difficult to determine which molecules are responsible for the observed biological effects. Recently, several single chitooligosaccharides have been obtained by chemical synthesis [11, 12] and chromatographic separation [13, 14]. In particular, of these single chitooligosaccharides, chitohexaose ((GlcN) 6 , D6) is of a great interest due to its special bioactivities.…”

Section: Introductionmentioning

confidence: 99%

Access to N-Acetylated Chitohexaose with Well-Defined Degrees of Acetylation

Xing

Liu

et al. 2017

BioMed Research International

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Chitohexaose has attracted wide interest due to its special bioactivities and these potential activities are significantly related to N-acetylation. Herein, six chitohexaose fractions with different degrees of acetylation were prepared by selective N-acetylation and ion-exchange chromatography and further analyzed by ESI/MS. It is revealed that all the six N-acetylated chitohexaoses were of single molecular weight, the molecular weights of which were exactly assigned to 1026.44 Da, 1068.44 Da, 1110.48 Da, 1152.48 Da, 1194.49 Da, and 1236.48 Da, respectively. These results suggested that the six prepared N-acetylated chitohexaoses were N-acetylchitohexaose (D5A1), di-N-acetylchitohexaose (D4A2), tri-N-acetylchitohexaose (D3A3), tetra-N-acetylchitohexaose (D2A4), penta-N-acetylchitohexaose (D1A5), and hexa-N-acetylchitohexaose (A6), respectively, which are of great significance to screen their bioactivities and discover well-defined chitooligosaccharide molecules as potential drugs.

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Synthesis of chitotetraose and chitohexaose based on dimethylmaleoyl protection

Cited by 41 publications

References 16 publications

Production of Chitooligosaccharides and Their Potential Applications in Medicine

Production of Chitooligosaccharides and Their Potential Applications in Medicine

Biotechnological approaches for field applications of chitooligosaccharides (COS) to induce innate immunity in plants

Access to N-Acetylated Chitohexaose with Well-Defined Degrees of Acetylation

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