Lipase-catalysed preparation of acetates of 4-nitrophenyl β-d-xylopyranoside and their use in kinetic studies of acetyl migration

Mastihubová, Mária; Biely, Peter

doi:10.1016/j.carres.2004.02.016

Cited by 63 publications

(41 citation statements)

References 31 publications

(9 reference statements)

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“…Acetylation occurs mainly in hardwood (acetyl glucuronoxylan), typically at the C2 or C3 or both positions, depending on whether it is a mono-or di-O-acetylated xylopyranosyl unit ( Figure 3). On non-reducing xylopyranosyl residues of oligosaccharides or xylopyranosides, acetyl groups can migrate to position C4 [5,16]. The migration is accelerated by increased pH and temperature [17].…”

Section: Acetylated Xylanmentioning

confidence: 99%

“…The first AcXE assigned to the CE5 family [81] was isolated from Trichoderma reesei and showed similarly as CE4 esterases. some requirement for a free unsubstituted hydroxyl group for deacetylation of adjacent positions [16]. Other characterized CE5 AcXEs have been isolated from Chrysosporium lucknowense C1 [62], Penicillium aurantiogriseum [83] and P. purpurogenum MYA 38 [84].…”

Section: Ce5mentioning

confidence: 99%

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Phylogeny, classification and metagenomic bioprospecting of microbial acetyl xylan esterases

Adesioye

Makhalanyane

Biely

et al. 2016

Enzyme and Microbial Technology

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Highlights• AcXEs occur in several CAZy families, and show promiscuous substrate specificities.• A strong AcXE sequence to specificity link would be a valuable functional predictor.• There is a clear need for novel AcXE enzymes with detailed substrate specificity data.• Functional metagenomics would be the most effective means for identifying new AcXEs.• A lack of suitable substrates limits high throughput metagenomic biomining of AcXEs.

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Section: Acetylated Xylanmentioning

confidence: 99%

Section: Ce5mentioning

confidence: 99%

Phylogeny, classification and metagenomic bioprospecting of microbial acetyl xylan esterases

Adesioye

Makhalanyane

Biely

et al. 2016

Enzyme and Microbial Technology

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“…a Data collection, data processing, structure solution and structure refinement, respectively. (5) 7395 (4) 7917 (2) 2654 (1) 26(1) C (6) 10142 (3) 5432 (2) 3110 (1) 20(1) C (7) 9400 (3) 4503 (2) 3540 (1) 20(1) C (8) 7385 (4) 4212 (2) 3549 (1) 27(1) C (9) 6714 (4) 3309 (2) 3917 (1) 31(1) C (10) 8033 (3) 2681 (2) 4273 (1) 28(1) C (11) 10026 (3) 2981 (2) 4276 (1) 28(1) C (12) 10712 (4) 3890 (2) 3908 (1) 23(1) C (13) 6554 (3) 5179 (2) 938 (1) 20(1) C (14) 6490 (3) 3994 (2) 642 (1) 18(1) C (15) 6413 (3) 3972 (2) 13 (1) 21 (1) (2) 27 (1) 30 (1) 39 (1) 1 (1) 3(1) -7(1) O (3) 30 (1) 18 (1) 16 (1) 1(1) -2(1) -2(1) O …”

Section: Single-crystal X-ray Structure Determinationsunclassified

“…[8][9][10] The chemical complexity of carbohydrate derivatives, due to subtle differences in reactivity of the various hydroxyl groups and the possible formation of species co-existing in equilibrium under different reaction conditions, may lead to unexpected processes ranging from rearrangements to functional group migrations. 11,12 In many cases, single crystal X-ray analysis is the only reliable method for correct structural and conformational assignments. 13,14 Aldonolactones 15 (modified sugars with the anomeric centre in its higher oxidation state) have been widely employed in synthesis as an alternative to simple carbohydrates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel O-acylated-D-ribono-1,5-lactones and structural assignment supported by conventional NOESY-NMR and x-ray analysis

Sá¹,

Silveira²,

Miguel³

et al. 2008

J. Braz. Chem. Soc.

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Este trabalho apresenta um método simples para a caracterização estrutural de 3,4-O-benzilideno-D-ribono-1,5-lactonas e análogos, fundamentado em técnicas convencionais de RMN e experimentos de NOESY em solução. 2-O-Acil-3,4-O-benzilideno-D-ribono-1,5-lactonas foram preparadas em bons rendimentos a partir da acilação das lactonas de Zinner empregando cloretos de ácido sob condições básicas. A estrutura de 2-O-(4-nitrobenzoil)-3,4-O-benzilideno-D-ribono-1,5-lactona foi determinada por difração de raios-X e confirmou, de forma inequívoca, os dados espectroscópicos obtidos.A practical method for the structural assignment of 3,4-O-benzylidene-D-ribono-1,5-lactones and analogues using conventional NMR techniques and NOESY measurements in solution is described. 2-O-Acyl-3,4-O-benzylidene-D-ribono-1,5-lactones were prepared in good yields by acylation of Zinner's lactone with acyl chlorides under mildly basic conditions. Structural determination of 2-O-(4-nitrobenzoyl)-3,4-O-benzylidene-D-ribono-1,5-lactone was achieved by single crystal x-ray diffraction, which supports the results based on spectroscopic data. Keywords:O-acyl-D-ribono-1,5-lactones, D-ribono-1,4-lactones, structural elucidation, sugar lactones, acylation IntroductionSeveral carbohydrates are easily available from renewable resources 1,2 and constitute a major class of building blocks for the synthesis of natural products and biologically active compounds. [3][4][5][6][7] However, the synthesis of novel carbohydrate-based molecules and their unequivocal structural elucidation are usually difficult to accomplish by simple and predictable methods. [8][9][10] The chemical complexity of carbohydrate derivatives, due to subtle differences in reactivity of the various hydroxyl groups and the possible formation of species co-existing in equilibrium under different reaction conditions, may lead to unexpected processes ranging from rearrangements to functional group migrations. 11,12 In many cases, single crystal X-ray analysis is the only reliable method for correct structural and conformational assignments. 13,14 Aldonolactones 15 (modified sugars with the anomeric centre in its higher oxidation state) have been widely employed in synthesis as an alternative to simple carbohydrates. D-Ribono-1,4-lactone (D-ribono--lactone, 1) is one of the most useful chiral precursors from this class, [16][17][18][19] although the issues associated with product characterization due to unpredictable transformations are also present to a great extent. For instance, the product obtained from the reaction of D-ribono-1,4-lactone (1) with benzaldehyde in acidic medium, which was initially assigned as being 3,5-O-benzylidene-D-ribono-1,4-lactone (2), 20,21 had the correct structure unequivocally established as 3,4-O-benzylidene-D-ribono-1,5-lactone (3) by single crystal X-ray diffraction analysis of its O-acetyl derivative (Scheme 1). 22 A complex rearrangement involving acetal migration and ring expansion sequences has been proposed for this transformation. 10,14 Therefore, the sc...

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“…The degree of acetylation varies based on the type of tissue and plant species; it was reported that the degree of acetylation varied between 0.60 and 0.75 in glucuronoxylan of aspen wood and 0.3 and 0.4 in galactoglucomannan of spruce, aspen and birch wood (Teleman et al 2000, 2003). The acetyl groups were also found to migrate between the neighbouring free hydroxyl groups and the positions of which varies based on the species (Pauly 1999; Jacobs et al 2002; Mastihubová and Biely 2004) (Table 1). …”

Section: Introductionmentioning

confidence: 99%

Understanding the structural and functional properties of carbohydrate esterases with a special focus on hemicellulose deacetylating acetyl xylan esterases

Kameshwar

Qin

2018

Mycology

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Acetyl and methyl esterifications are two major naturally found substitutions in the plant cell-wall polysaccharides. The non-cellulosic plant cell-wall polysaccharides such as pectin and hemicellulose are differentially esterified by the O-acetyl and methyl groups to cease the action of various hydrolytic enzymes secreted by different fungi and bacterial species. Thus, microorganisms have emerged with a special class of enzymes known as carbohydrate esterases (CE). The CE catalyse O-de, N-deacetylation of acetylated saccharide residues (esters or amides, where sugars play the role of alcohol/amine/acid). Carbohydrate active enzyme (CAZy) database has classified CE into 16 classes, of which hemicellulose deacetylating CE were grouped into eight classes (CE-1 to CE-7 and CE-16). Various plant biomass degrading fungi and bacteria secretes acetyl xylan esterases (AcXE); however, these enzymes exhibit varied substrate specificities. AcXE and xylanases-coupled pretreatment methods exhibit significant applications, such as enhancing animal feedstock, baking industry, production of food additives, paper and pulp, xylitol production and biorefinery-based industries, respectively. Thus, understanding the structural and functional properties of acetyl xylan esterase will significantly aid in developing the efficient AcXE with wide range of industrial applications.

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Lipase-catalysed preparation of acetates of 4-nitrophenyl β-d-xylopyranoside and their use in kinetic studies of acetyl migration

Cited by 63 publications

References 31 publications

Phylogeny, classification and metagenomic bioprospecting of microbial acetyl xylan esterases

Phylogeny, classification and metagenomic bioprospecting of microbial acetyl xylan esterases

Synthesis of novel O-acylated-D-ribono-1,5-lactones and structural assignment supported by conventional NOESY-NMR and x-ray analysis

Understanding the structural and functional properties of carbohydrate esterases with a special focus on hemicellulose deacetylating acetyl xylan esterases

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