Production and chitinase-binding ability of lipo-chitopentaose nodulation factor

Huang, Gangliang; Mei, Xiaoguang

doi:10.1080/14756360601073740

Cited by 3 publications

(1 citation statement)

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“…[37] Having deacetylated the product, a biotin group (8) or a lipid chain (17) could be attached by using an N-hydroxysuccinimide (NHS) ester as depicted in Scheme 2. A similar strategy for synthesizing a Nod factor, V(C18:0), was utilized by Huang and Mei [38] by using an acid chloride for acylation. However, in our hands, the NHS approach was preferred because of its stability and water compatibility.…”

Section: Lipochitin Oligosaccharides and Peptidoglycan Synthesismentioning

confidence: 99%

Lipochitin Oligosaccharides Immobilized through Oximes in Glycan Microarrays Bind LysM Proteins

et al. 2014

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Glycan microarrays have emerged as novel tools to study carbohydrate-protein interactions. Here we describe the preparation of a covalent microarray with lipochitin oligosaccharides and its use in studying proteins containing LysM domains. The glycan microarray was assembled from glycoconjugates that were synthesized by using recently developed bifunctional chemoselective aminooxy reagents without the need for transient carbohydrate protecting groups. We describe for the first time the preparation of a covalent microarray with lipochitin oligosaccharides and its use for studying proteins containing LysM domains. Lipochitin oligosaccharides (also referred to as Nod factors) were isolated from bacterial strains or chemoenzymatically synthesized. The glycan microarray also included peptidoglycan-related compounds, as well as chitin oligosaccharides of different lengths. In total, 30 ligands were treated with the aminooxy linker molecule. The identity of the glycoconjugates was verified by mass spectrometry, and they were then immobilized on the array. The presence of the glycoconjugates on the array surface was confirmed by use of lectins and human sera (IgG binding). The functionality of our array was tested with a bacterial LysM domain-containing protein, autolysin p60, which is known to act on the bacterial cell wall peptidoglycan. P60 showed specific binding to Nod factors and to chitin oligosaccharides. Increasing affinity was observed with increasing chitin oligomer length.

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Section: Lipochitin Oligosaccharides and Peptidoglycan Synthesismentioning

confidence: 99%

Lipochitin Oligosaccharides Immobilized through Oximes in Glycan Microarrays Bind LysM Proteins

et al. 2014

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Synthesis and stability assay of 4-methylumbelliferyl (1→3)-β-D-pentaglucoside

Huang

2008

Journal of Enzyme Inhibition and Medicinal Chemistry

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The synthesis and stability of 4-methylumbelliferyl (1 ! 3)-b-D-pentaglucoside 3 are described. The (1 ! 3)-b-D-glucan isolated from the cell walls of Saccharomyces cerevisiae was recovered from the aqueous medium as water-insoluble particles by the spray drying (GS) method. (SnCl 4 ) catalyst. NaOMe in dry methanol was used for the deacetylation of the blocked derivative, to give the target compound 3 in an overall yield of 35%. Activity assays with b-glucosidase indicated that compound 3 was much more stable than the corresponding pentasaccharide.

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The cell factory approach toward biotechnological production of high-value chitosan oligomers and their derivatives: an update

Naqvi

Moerschbacher

2015

Critical Reviews in Biotechnology

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Chitin is one of the most abundant renewable resources, and chitosans, the partially deacetylated derivatives of chitin, are among the most promising functional biopolymers, with superior material properties and versatile biological functionalities. Elucidating molecular structure-function relationships and cellular modes of action of chitosans, however, it is challenging due to the micro-heterogeneity and structural complexity of polysaccharides. Lately, it has become apparent that many of the biological activities of chitosan polymers, such as in agricultural plant disease protection or in mediating scar-free wound healing, may be attributed to oligomeric break-down products generated by the action of chitosanolytic hydrolases present in the target tissues, such as human chitotriosidase. Consequently, the focus of current research is shifting toward chitosan oligomers so that the availability of well-defined chitosan oligosaccharides (COS) becomes a bottleneck. Well-known ways of producing COS use physical and/or chemical means for the partial depolymerization of chitosan polymers, typically leading to broad mixtures of COS varying in their degrees of polymerization (DP) and acetylation (DA), and with more or less random patterns of acetylation (PAs). Even after chromatographic separation according to DP and DA, such mixtures are of limited value to elucidate structure-function relationships and modes of action. More recently, enzymatic means using chitinases and/or chitosanases, and sometimes chitin deacetylases, have been proposed as these can be more tightly controlled and yield slightly better defined mixtures of COS. An alternative would be chemical synthesis of COS which in principle would allow for full structural control, but protocols for it are lengthy, costly, and not yet well developed, and yields are low. Synthetic biology now allows to develop today's in vitro bio-refinery approaches into in vivo cell factory approaches for the biotechnological production of defined COS using recombinant microbial strains expressing chitin oligomer synthases and chitin oligomer deacetylases. In this review, we will describe the state-of-the-art of this cell factory approach, as a basis for upcoming developments. We will briefly describe traditional chemical protocols and enzymatic production of COS as a background to the more detailed presentation of what has been achieved through in vivo biosynthesis. We will only briefly describe those as a background to the more detailed presentation of what has been achieved through in vivo biosynthesis. We will also touch on the production of COS derivatives that has been achieved in this way, as these oligomers open up another plethora of potential applications when used as building blocks for defined biomaterials.

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Production and chitinase-binding ability of lipo-chitopentaose nodulation factor

Cited by 3 publications

References 7 publications

Lipochitin Oligosaccharides Immobilized through Oximes in Glycan Microarrays Bind LysM Proteins

Lipochitin Oligosaccharides Immobilized through Oximes in Glycan Microarrays Bind LysM Proteins

Synthesis and stability assay of 4-methylumbelliferyl (1→3)-β-D-pentaglucoside

The cell factory approach toward biotechnological production of high-value chitosan oligomers and their derivatives: an update

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