608-66-2Relevant articles and documents
C3 Epimerization of Glucose, via Regioselective Oxidation and Reduction
Jumde, Varsha R.,Eisink, Niek N. H. M.,Witte, Martin D.,Minnaard, Adriaan J.
, p. 11439 - 11443 (2016)
Palladium-catalyzed oxidation can single out the secondary hydroxyl group at C3 in glucose, circumventing the more readily accessible hydroxyl at C6 and the more reactive anomeric hydroxyl. Oxidation followed by reduction results in either allose or allitol, each a rare sugar that is important in biotechnology. Also, N-acetylglucosamine is selectively oxidized at C3. These results demonstrate that glucose and N-acetylglucosamine, the most readily available chiral building blocks, can be versatile substrates in homogeneous catalysis.
Three new cycloartenol triterpenoid saponins from the roots of cimicifuga simplex wormsk
Kuang, Haixue,Su, Yang,Yang, Bingyou,Xia, Yonggang,Wang, Qiuhong,Wang, Zhibin,Yu, Zhengfan
, p. 4348 - 4357 (2011)
Three new cycloartenol triterpene saponins, named shengmaxinsides A-C, have been isolated from the ethyl acetate soluble fraction of an ethanol extract of Cimicifuga simplex Wormsk roots. Their structures were established by chemical tests and detailed spectroscopic analysis as 25-O-acetyl-7,8-didehydrocimigenol- 3-O-β-D-galactopyranoside (1), 7,8-didehydrocimigenol-3-O-β-D- galactopyranoside (2) and 7,8-didehydro-24S-Oacetylhydroshengmanol- 3-O-β-D-galactopyranoside (3), respectively.
A novel low-molecular-mass pumpkin polysaccharide: Structural characterization, antioxidant activity, and hypoglycemic potential
Huang, Linlin,Li, Fei,Li, Quanhong,Liang, Li,Wei, Yunlu,Yu, Guoyong
, (2020/10/02)
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.
Structural features and antioxidant activity of a new galactoglucan from edible mushroom Pleurotus djamor
Maity, Gajendra Nath,Maity, Prasenjit,Khatua, Somanjana,Acharya, Krishnendu,Dalai, Sudipta,Mondal, Soumitra
, p. 743 - 749 (2020/12/07)
A new water soluble galactoglucan with apparent molecular weight ~1.61 × 105 Da, was isolated from the edible mushroom Pleurotus djamor by hot water extraction followed by purification through dialysis tubing cellulose membrane and sepharose 6B column chromatography. The sugar analysis showed the presence of glucose and galactose in a molar ratio of nearly 3:1 respectively. The structure of the repeating unit in the polysaccharide was determined through chemical and NMR experiments as:[Formula presented] In vitro antioxidant studies showed that the PDPS exhibited hydroxyl radical scavenging activity (EC50 = 1.681 ± 0.034 mg/mL), DPPH radical scavenging activity (EC50 = 3.83 ± 0.427 mg/mL), reducing power (EC50 = 4.258 ± 0.095 mg/mL), and ABTS radical quenching activity (EC50 = 0.816 ± 0.077 mg/mL). So, PDPS should be explored as a natural antioxidant.
Selective and Scalable Synthesis of Sugar Alcohols by Homogeneous Asymmetric Hydrogenation of Unprotected Ketoses
Tindall, Daniel J.,Mader, Steffen,Kindler, Alois,Rominger, Frank,Hashmi, A. Stephen K.,Schaub, Thomas
supporting information, p. 721 - 725 (2020/10/19)
Sugar alcohols are of great importance for the food industry and are promising building blocks for bio-based polymers. Industrially, they are produced by heterogeneous hydrogenation of sugars with H2, usually with none to low stereoselectivities. Now, we present a homogeneous system based on commercially available components, which not only increases the overall yield, but also allows a wide range of unprotected ketoses to be diastereoselectively hydrogenated. Furthermore, the system is reliable on a multi-gram scale allowing sugar alcohols to be isolated in large quantities at high atom economy.
Elucidating the effect of solid base on the hydrogenation of C5 and C6 sugars over Pt–Sn bimetallic catalyst at room temperature
Tathod, Anup P.,Dhepe, Paresh L.
, (2021/05/19)
Conversion of sugars into sugar alcohols at room temperature with exceedingly high yields are achieved over Pt–Sn/γ-Al2O3 catalyst in the presence of calcined hydrotalcite. pH of the reaction mixture significantly affects the conversion and selectivity for sugar alcohols. Selection of a suitable base is the key to achieve optimum yields. Various solid bases in combination with Pt–Sn/γ-Al2O3 catalysts were evaluated for hydrogenation of sugars. Amongst all combinations, the mixture (1:1 wt/wt) of Pt–Sn/γ-Al2O3 and calcined hydrotalcite showed the best results. Hydrotalcite helps to make the pH of reaction mixture alkaline at which sugar molecules undergo ring opening. The sugar molecule in open chain form has carbonyl group which can be polarized by Sn in Pt–Sn/γ-Al2O3 and Pt facilitates the hydrogenation. In the current work, effect of both; solid base and Sn as a promoter has been studied to improve the yields of sugar alcohols from various C5 and C6 sugars at very mild reaction conditions.
L-Xylo-3-hexulose, a new rare sugar produced by the action of acetic acid bacteria on galactitol, an exception to Bertrand Hudson's rule
Xu, Yirong,Chi, Ping,Lv, Jiyang,Bilal, Muhammad,Cheng, Hairong
, (2020/10/02)
Background: In acetic acid bacteria such as Gluconobacter oxydans or Gluconobacter cerinus, pyrroloquinoline quinone (PQQ) in the periplasm serves as the redox cofactor for several membrane-bound dehydrogenases that oxidize polyhydric alcohols to rare sugars, which can be used as a healthy alternative for traditional sugars and sweeteners. These oxidation reactions obey the generally accepted Bertrand Hudson's rule, in which only the polyhydric alcohols that possess cis D-erythro hydroxyl groups can be oxidized to 2-ketoses using PQQ as a cofactor, while the polyhydric alcohols excluding cis D-erythro hydroxyl groups ruled out oxidation by PQQ-dependent membrane-bound dehydrogenases. Methods: Membrane fractions of G. oxydans were prepared and used as a cell-free catalyst to oxidize galactitol, with or without PQQ as a cofactor. Results: In this study, we reported an interesting oxidation reaction that the polyhydric alcohols galactitol (dulcitol), which do not possess cis D-erythro hydroxyl groups, can be oxidized by PQQ-dependent membrane-bound dehydrogenase(s) of acetic acid bacteria at the C-3 and C-5 hydroxyl groups to produce rare sugars L-xylo-3-hexulose and D-tagatose. Conclusions: This reaction may represent an exception to Bertrand Hudson's rule. General significance: Bertrand Hudson's rule is a well-known theory in polyhydric alcohols oxidation by PQQ-dependent membrane-bound dehydrogenase in acetic acid bacteria. In this study, galactitol oxidation by a PQQ-dependent membrane-bound dehydrogenase represents an exception to the Bertrand Hudson's rule. Further identification of the associated enzymes and deciphering the explicit enzymatic mechanism will prove this theory.
Direct conversion of cellulose into isosorbide over Ni doped NbOPO4catalysts in water
Guo, Jiaxing,He, Minyao,Li, Cuiqing,Liu, ShanShan,Song, Yongji,Wang, Hong,Wang, Xincheng
supporting information, p. 10292 - 10299 (2020/07/14)
Isosorbide is a versatile chemical intermediate for the production of a variety of drugs, chemicals, and polymers, and its efficient production from natural cellulose is of great significance. In this study, bifunctional catalysts based on niobium phosphates were prepared by a facile hydrothermal method and used for the direct conversion of cellulose to isosorbide under aqueous conditions. NH3-TPD analysis showed that a high acid content existed on the catalyst surface, and pyridine infrared spectroscopic analysis confirmed the presence of both Lewis acid and Br?nsted acid sites, both of which played an important role in the process of carbohydrate conversion. XRD and H2-TPR characterization determined the composition and the hydrogenation centers of the catalyst. An isosorbide yield of 47% could be obtained at 200 °C for 24 h under 3 MPa H2 pressure. The Ni/NbOPO4 bifunctional catalyst retains most of its activity after five consecutive runs with slightly decreased isosorbide yield of 44%. In addition, a possible reaction mechanism was proposed that the synergistic effect of surface acid sites and hydrogenation sites was favorable to enhancing the cascade dehydration and hydrogenation reactions during the conversion of cellulose to isosorbide. This study provides as an efficient strategy for the development of novel multifunctional heterogeneous catalysts for the one-pot valorisation of cellulose. This journal is
Highly efficient catalytic conversion of cellulose into acetol over Ni-Sn supported on nanosilica and the mechanism study
Liu, Xiaohao,Liu, Xiaodong,Xu, Guangyue,Zhang, Ying,Wang, Chenguang,Lu, Qiang,Ma, Longlong
, p. 5647 - 5656 (2019/11/05)
Selective conversion of cellulose into high value-added C3 chemicals is a great challenge in biorefinery due to the complicated reaction process. In this work, 61.6% yield of acetol was obtained by one pot conversion of cellulose using Ni-Sn/SiO2 catalysts. A series of characterization methods including TEM, STEM-HAADF, EDS, AAS, XRD, XPS, H2-TPR, Py-FTIR, and CO2-TPD were carried out to explore the structure-activity relationship. The strong basicity of the catalysts was a key factor affecting the production of acetol. In addition, catalysts with the hydrothermally stable L-acid sites and no B-acid sites inhibited side reactions and ensured efficient conversion of cellulose into small molecules. Further studies showed that the formation of the Ni3Sn4 alloy significantly promoted the acetol production, and its weak hydrogenation activity inhibited further conversion of acetol. Noninteger valence tin species (Snδ+ and SnOx) were formed both in Ni3Sn4 and Sn/SiO2. These Sn species were the source of basic sites and the active sites for catalyzing cellulose to acetol. Under the synergistic catalysis of Sn/SiO2 and the Ni3Sn4 alloy, cellulose was efficiently converted into acetol. This work provides guidance for the selective conversion of cellulose into C3 products.
Synthesis method of partially methylated alditol acetate of monosaccharides
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Paragraph 0022; 0033-0034, (2019/10/10)
The invention discloses a synthesis method of partially methylated alditol acetate of monosaccharides, and belongs to the field of synthesis of partial methylation of the monosaccharides. The synthesis method comprises the following steps: (1) performing a reduction reaction on the monosaccharides to generate a corresponding alditol product; (2) performing a partial methylation reaction on the alditol product obtained through the reduction reaction; (3) performing an acetylation reaction on a product of the partial methylation reaction to obtain the partially methylated alditol acetate of the monosaccharides. Compared with an existing five-step synthesis method, the three-step synthesis method disclosed by the invention can simultaneously synthesize partially methylated alditol acetate compounds of furan and pyran type complete characteristics; meanwhile, the methylated reaction time is effectively shortened, so that hydroxyl groups are more rapidly methylated; compared with the same methylation time, the three-step synthesis method disclosed by the invention obviously improves a peak response value, and has the advantages of less synthesis steps, high strength, large quantity, high yield, simplicity and rapidness, and the like.
