7643-75-6

Usage

Uses

Used in Food Industry:
L-(-)-Arabitol is used as a food additive for its ability to reduce fat deposits in the intestines, which can contribute to a healthier diet and potentially aid in weight management.
Used in Biotechnology:
L-(-)-Arabitol is used as an inducer of xylanase expression in Hypocrea jecorina (Trichoderma reesei), a fungus that is important in the production of enzymes used in various industrial processes, such as biofuels and textiles.
Used in Enzyme Research:
L-(-)-Arabitol is used to identify, differentiate, and characterize L-arabitol dehydrogenase(s), enzymes that play a role in the metabolism of L-arabitol and can be important in understanding and developing applications related to sugar alcohol metabolism.

Purification Methods

This pentol, which occurs in the urine of pentosuric subjects, is purified by recrystallisation from 90% EtOH or MeOH. It has a higher rotation in the presence of molybdate: [] 20D -130o (c 0.16, acidified molybdate) [Richtmeyer & Hudson J Am Chem Soc 73 2249 1957]. [G.tzi & Reichstein Helv Chim Acta 21 197 1938, Beilstein 1 IV 2832.]

InChI:InChI=1/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m0/s1

Upstream product

• 5328-37-0 L-arabinose 
• 87-72-9 L-(+)-arabinose 
• 28697-53-2 D-arabinopyranose 
• 91-09-8 methyl β-L-arabinopyranoside 
• 38029-69-5 α-L-arabinofuranoside 
• 1949-78-6 L-lyxose 
• 532-20-7 L-arabinose 
• 58-86-6 D-xylose 
• 87-99-0 XYLITOL 
• 488-81-3 Adonitol 
• 9004-34-6 cellulose 
• 53106-52-8 DL-xylose 
• 50-70-4 sorbitol 
• 87-72-9 D-Xylose 

Downstream Products

• 96871-07-7 1,5-Di-O-trityl-L-arabinitol 
• 5346-78-1 1,2,3,4,5-penta-O-acetyl-L-arabinitol 
• 68679-85-6 1,3-O-Benzylidene-L-arabinitol 
• 1236198-02-9 1,3-O-benzylidene-L-arabitol 
• 36030-82-7 1,2,3,4,5-penta-O-benzoyl-L-arabinitol 
• 84709-35-3 2,3:4,5-bis-O-(1-methylethylidene)-L-arabinitol 
• 104196-15-8 lyxonic acid-1,4-lactone 
• 51532-86-6 L-arabino-1,4-lactone 
• 5328-37-0 L-arabinose 
• 34557-54-5 methane 
• 463-79-6 carbonic-acid 
• 947674-13-7 1-O-benzoyl-2,3:4,5-di-O-(1-methylidene)-L-arabitol 
• 506418-11-7 (5R)-4-[(1R)-1,2-(dihydroxy)ethyl]-5-hydroxymethylfuran-2-(5H)-one 

Relevant academic research and scientific papers

Action patterns and mapping of the substrate-binding regions of endo-(1 → 5)-α-L-arabinanases from Aspergillus niger and Aspergillus aculeatus

The substrate binding sites of endo-(1 → 5)-α-L-arabinanases (EC 3.2.1.99) from Aspergillus niger and Aspergillus aculeatus were investigated using reduced and regular (1 → 5)-α-L-arabino-oligosaccharides and high performance anion exchange chromatographic analysis. Calculation of bond cleavage frequencies and k(cat)/K(m), parameters for these substrates enabled the determination of the number of arabinofuranosyl binding subsites and the estimation of the binding affinities of each subsite. The A. aculeatus endo-arabinanase has six subsites arranged symmetrically around the catalytic site, while the A. niger endo-arabinanase has five subsites; two from the catalytic site towards the non-reducing end of the bound substrate and three toward the reducing end. The two subsites directly adjacent to the catalytic sites in both the A. niger and A. aculeatus endo-arabinanase have near-zero net free energy of binding. These results are unlike most glycopyranosyl endo-hydrolases studied which have net negative (unfavourable) energies of interaction at these two subsites, and may be related to the greater conformational flexibility of arabinofuranosyl residues than glycopyranosyl residues. The complete subsite maps are also rationalized with regard to the observed action patterns of these enzymes on linear (1 → 5)-α-L-arabinan.

A novel low-molecular-mass pumpkin polysaccharide: Structural characterization, antioxidant activity, and hypoglycemic potential

The novel natural low-molecular-mass polysaccharide (SLWPP-3) from pumpkin (Cucurbia moschata) was separated from the waste supernatant after macromolecular polysaccharide production and purified using a DEAE cellulose-52 column and gel-filtration chromatography. Chemical and instrumental studies revealed that SLWPP-3 with a molecular mass of 3.5 kDa was composed of rhamnose, glucose, arabinose, galactose and uronic acid with a weight ratio of 1: 1: 4: 6: 15, and primarily contained →3,6)-β-D-Galp-(1→, →4)-α-GalpA-(1→(OMe), →4)-α-GalpA-(1→, →2,4)-α-D-Rhap-(1→, →3)-β-D-Galp-(1→, →4)-α-D-Glcp, and →4)-β-D-Galp residues in the backbone. The branch chain passes were connected to the main chain through the O-4 atom of glucose and O-3 atom of arabinose. Physiologically, the ability of SLWPP-3 to inhibit carbohydrate-digesting enzymes and DPPH and ABTS radicals, as well as protect pancreatic β cells from oxidative damage by decreasing MDA levels and increasing SOD activities, was confirmed. The findings elucidated the structural types of pumpkin polysaccharides and revealed a potential adjuvant natural product with hypoglycemic effects.

Hydrogenolysis of sorbitol into valuable C3-C2 alcohols at low H2 pressure promoted by the heterogeneous Pd/Fe3O4 catalyst

The hydrogenolysis of sorbitol and various C5-C3 polyols (xylitol; erythritol; 1,2- 1,4- and 2,3-butandiol; 1,2-propandiol; glycerol) have been investigated at low molecular hydrogen pressure (5 bar) by using Pd/Fe3O4, as heterogeneous catalyst and water as the reaction medium. Catalytic experiments show that the carbon chain of polyols is initially shortened through dehydrogenation/decarbonylation and dehydrogenation/retro-aldol mechanisms followed by a series of cascade reactions that include dehydrogenation/decarbonylation and dehydration/hydrogenation processes. At 240 °C, sorbitol is fully converted into lower alcohols with ethanol being the main reaction product in liquid phase.

Discovery and characterization of family 39 glycoside hydrolases from rumen anaerobic fungi with polyspecific activity on rare arabinosyl substrates

Enzyme activities that improve digestion of recalcitrant plant cell wall polysaccharides may offer solutions for sustainable industries. To this end, anaerobic fungi in the rumen have been identified as a promising source of novel carbohydrate active enzymes (CAZymes) that modify plant cell wall polysaccharides and other complex glycans. Many CAZymes share insufficient sequence identity to characterized proteins from other microbial ecosystems to infer their function; thus presenting challenges to their identification. In this study, four rumen fungal genes (nf2152, nf2215, nf2523, and pr2455) were identified that encode family 39 glycoside hydrolases (GH39s), and have conserved structural features with GH51s. Two recombinant proteins, NF2152 and NF2523, were characterized using a variety of biochemical and structural techniques, and were determined to have distinct catalytic activities. NF2152 releases a single product, β1,2-arabinobiose (Ara2) from sugar beet arabinan (SBA), and β1,2-Ara2 and α-1,2-galactoarabinose (Gal-Ara) from rye arabinoxylan (RAX). NF2523 exclusively releases α-1,2-Gal-Ara from RAX, which represents the first description of a galacto-(-1,2)-arabinosidase. Both β-1,2-Ara2 and α-1,2-Gal-Ara are disaccharides not previously described within SBA and RAX. In this regard, the enzymes studied here may represent valuable new biocatalytic tools for investigating the structures of rare arabinosyl-containing glycans, and potentially for facilitating their modification in industrial applications.

Preparation method of gamma-acetyl n-propanol

The invention discloses a preparation method of gamma-acetyl n-propanol. The method includes the steps of (1) adding the hydrolysate of plant fiber or xylose and other raw materials into a reaction still, adding a two-phase reactive solvent and a catalyst, inletting hydrogen, and heating the reaction still to react for several hours; (2) carrying out standing, liquid separation and then solid-liquid separation on reaction materials in the reaction still, obtaining water phase, oil phase and the catalyst, and recycling the catalyst for reutilization; (3) concentrating water phase products, extracting 1, 4-pentanediol in the oil phase, mixing with the concentrated solution, and carrying out further separation to obtain a crude product of 1, 4-pentanediol; (4) pumping the crude product of 1, 4-pentanediol obtained from the water phase and the oil phase in step (3) to a fixed bed reactor, carrying out dehydrogenation to produce gamma-acetyl n-propanol under the action of a catalytic dehydrogenation catalyst or an oxydehydrogenation catalyst. According to the preparation method, raw materials have extensive sources, the production cost is low, no inorganic acid system is used, and the reaction process is environment-friendly.

CTAB-assisted sol-microwave method for fast synthesis of mesoporous TiO2 photocatalysts for photocatalytic conversion of glucose to value-added sugars

Fabrication technique is an important factor for development of catalysts. Titanium dioxide (TiO2) is one of efficient photocatalysts. In this work, we firstly report the fabrication of TiO2 nanoparticles by sol-microwave method with cetyltrimethylammonium bromide (CTAB) surfactant. Absence of surfactant, microwave treatment significantly reduced the cluster sizes of TiO2, but high aggregations of TiO2 particles were observed. CTAB has great impact on morphology, cluster size and mesoporous structure of TiO2. Therefore, surface area of TiO2 synthesized by sol-microwave method with 0.108 M CTAB increased from 15.97 to 37.60 m2/g. Photocatalytic activity of TiO2 was tested via the glucose conversion to produce value-added chemicals (gluconic acid, xylitol, arabinose and formic acid). It was found that surface area, mesoporous structure and pore size of TiO2 are crucial properties for glucose conversion and product distribution. From the reaction test, 0.108 M CTAB/MW-TiO2 achieved the highest glucose conversion (62.28%).

Xylitol Hydrogenolysis over Ruthenium-Based Catalysts: Effect of Alkaline Promoters and Basic Oxide-Modified Catalysts

The aqueous-phase hydrogenolysis of xylitol into glycols over Ru/C was performed in the presence and absence of a wide range of concentrations of Ca(OH)2 to investigate the reaction pathway. Without base, epimerization and cascade decarbonylation were the predominant reactions with high selectivities to C5 and C4 alditols and light alkanes at full conversion. Glycol production was obtained by the addition of Ca(OH)2 to promote the retro-aldol reaction. It competed with reactions without base and became the main reaction for a OH?/ xylitol molar ratio Rmol(OH/xylitol) of 0.13, and high selectivities to glycols (56 %) and glycerol (16 %) were observed. However, lactate was a byproduct at up to 27 % with a high base amount (Rmol(OH/xylitol)=0.68). Bifunctional Ru/metal oxide/C catalysts (metal: Zn, Sn, Mn, Sr, W) were synthesized and were able to cleave the C?C bond into glycols without a base promoter. The 3.1 wt %Ru/MnO(4.5 %)/C catalyst was the most active (220 h?1) with reasonable selectivity to glycols (22 %) and glycerol (10 %) and a low production of lactate (1 %). Nevertheless, metal oxide leaching of the catalyst was observed likely because of the production of traces of lactate.

Characterization of the chemical diversity of glycosylated mycosporine-like amino acids in the terrestrial cyanobacterium Nostoc commune

Mycosporine-like amino acids (MAAs) are UV-absorbing pigments, and structurally unique glycosylated MAAs are found in the terrestrial cyanobacterium Nostoc commune. In this study, we examined two genotypes of N. commune colonies with different water extract UV-absorption spectra. We found structurally distinct MAAs in each genotype. The water extract from genotype A showed a UV-absorbing spectrum with an absorption maximum at 335 nm. The extract contained the following compounds: 7-O-(β-arabinopyranosyl)-porphyra-334 (478 Da), pentose-bound shinorine (464 Da), hexose-bound porphyra-334 (508 Da) and porphyra-334 (346 Da). The water extract from genotype B showed a characteristic UV-absorbing spectrum with double absorption maxima at 312 and 340 nm. The extract contained hybrid MAAs (1050 Da and 880 Da) with two distinct chromophores of 3-aminocyclohexen-1-one and 1,3-diaminocyclohexen linked to 2-O-(β-xylopyranosyl)-β-galactopyranoside. A novel 273-Da MAA with an absorption maximum at 310 nm was also identified in genotype B. The MAA consisted of a 3-aminocyclohexen-1-one linked to a γ-aminobutyric acid chain. These MAAs had potent radical scavenging activities in vitro and the results confirmed that the MAAs have multiple roles as a UV protectant and an antioxidant relevant to anhydrobiosis in N. commune. The two genotypes of N. commune exclusively produced their own characteristic glycosylated MAAs, which supports that MAA composition could be a chemotaxonomic marker for the classification of N. commune.

Selective terminal C-C scission of C5-carbohydrates

The selective catalytic production of C4-tetritols (erythritol and threitol) from C5-sugars is an attractive route for the conversion of non-digestible sugars to C4-building blocks from agro residues. Here we show that an unprecedented high selectivity of 20-25% C4-tertritols can be achieved under mild conditions (138 °C, 6 bar H2, and 24 h) in the aqueous conversion of xylose over a 5 wt% Ru/C catalyst. A mechanistic study revealed that the dominant reaction mechanism for C5-sugar conversion involves a formal decarbonylation step leading to the initial formation of the desired C4-tetritols. Subsequently the formed C4-tetritols undergo further terminal C-C scissions to glycerol and ethylene glycol. Remarkably, potentially competing reactions like internal C-C chain scission (fragmentation) or hydrodeoxygenation (HDO) do not occur to any significant extent under the applied conditions.

Water-soluble polysaccharides from finger citron fruits (Citrus medica L. var. sarcodactylis)

Four water-soluble polysaccharides, FCp-1, FCp-2, FCp-3, and FCp-4 were obtained from finger citron fruits (Citrus medica L. var. sarcodactylis) by hot-water extraction and ethanol precipitation, followed by routine separation procedure. Based on the calibration curve, molecular weights of them were estimated to be 113.9, 32.6, 140.3, and 177.1 kDa respectively. The acid hydrolysis, methylation, IR, GC-MS, and NMR experiments were used for composition analysis. FCp-1 was a heteropolysaccharide composed of arabinose, galactose, glucose, rhamnose, and xylose, with a molar ratio of 3.0:7.0:4.1:1.0:1.5. FCp-2 and FCp-4 were →4)-α-d-GalpA(1→ linking galacturonan differ in molecular weights. FCp-3 was a →6)-α-d-Glcp(1→ linking glucan. According to the results of in vitro assays, FCp-3 showed significantly and moderately enhancing capacities toward the proliferation of splenocytes and thymocytes respectively. Thus, FCp-3 or analogs may have further use as immunomodulatory agents.