Glycolaldehyde dimer
Manufactured by Merck Group
Sourced in Belgium
Glycolaldehyde dimer is a chemical compound used in laboratory settings. It is a symmetric dimeric form of glycolaldehyde, a simple sugar. The core function of glycolaldehyde dimer is as a chemical reagent and reference standard for analytical and research applications.
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Lab products found in correlation
Sodium hydroxide (naoh), by Thermo Fisher Scientific (2 mentions)
Hydrochloric acid (hcl), by Thermo Fisher Scientific (2 mentions)
Q sepharose, by GE Healthcare (2 mentions)
Triethanolamine hydrochloride, by Merck Group (2 mentions)
Sephacryl s 200, by GE Healthcare (2 mentions)
2 n morpholino ethanesulfonic acid sodium salt, by Merck Group (2 mentions)
Acetaldehyde, by Merck Group (2 mentions)
Fructose, by Merck Group (2 mentions)
Ethylene glycol, by Merck Group (2 mentions)
Glycerol, by Merck Group (2 mentions)
Dl glyceraldehyde, by Merck Group (2 mentions)
D glucose, by Merck Group (1 mentions)
Methanol, by Maclin Biochemical Technology (1 mentions)
D fructose, by Merck Group (1 mentions)
D mannose, by Merck Group (1 mentions)
D glyceraldehyde, by Merck Group (1 mentions)
Potassium carbonate, by Sinopharm (1 mentions)
Bca assay, by Thermo Fisher Scientific (1 mentions)
Gamma irradiated 10 kda cut off cassettes, by Thermo Fisher Scientific (1 mentions)
Milli q system, by Merck Group (1 mentions)
12 protocols using glycolaldehyde dimer
1
Catalytic Conversion of Carbohydrates
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d -(+)-Mannose (MAN, 99%), d -(+)-glucose (GLU, 99.5%), d -(−)-fructose (FRU, 99%), glycolaldehyde dimer (GA, 95%) and d -(−)-glyceraldehyde (GLA, 90%) were purchased from Sigma-Aldrich. Methyl glycolate (MG, 98%), 1,3-dihydroxyacetone (DHA, 99%), pyruvaldehyde (PYR, 40%), methyl lactate (ML, 98%), methanol (99.9%) were purchased from Macklin. Methyl glycerate (MGLY, 95%) was purchased from Molbase. Molybdenum(vi ) oxide (MoO3) and potassium carbonate were purchased from Sinopharm Chemical Reagent Company. Gold nanoparticle supported on titanium oxides (Au/TiO2: gold 1% on titanium dioxide) was purchased from Aladdin. Deionized water was produced by a laboratory water purification system.
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2
Glycolaldehyde-Derived AGEs Generation
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Glycolaldehyde-derived AGEs were generated under sterile conditions as described by Valencia et al.59 (link). Briefly, sterile filtered 30% BSA solution (Sigma, St. Louis, MO) was incubated with 70 mM glycolaldehyde dimer (Sigma) in sterile PBS without calcium chloride and magnesium chloride for three days at 37 °C. After incubation, the AGE product was dialyzed against sterile PBS for 24 hours at 4 °C using gamma-irradiated 10 kDa cut-off cassettes (Thermo Scientific, Waltham, MA) to remove unreacted glycolaldehyde. Unmodified control BSA was prepared similarly, without the addition of glycolaldehyde dimer. Protein concentration was determined by BCA assay (Thermo Scientific) and absence of endotoxin (<0.25Eu/ml) was confirmed via the LAL gel-clot assay (GenScript, Piscataway, NJ).
3
Hydrothermal Synthesis of Organic Solids
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The hydrothermal experiments were conducted following the method for the organic solid synthesis reported previously (16 , 50 ); the protocol was also based on previous work by Cody et al. (5 (link)) and Ricardo et al. (51 (link)). The starting solution contained Paraformaldehyde at 2 mmol (60 mg), glycolaldehyde at 1 mmol (60 mg), Ca(OH)2 [15 mg; given the low solubility in water, Ca(OH)2 exists largely as a solid], 4.9 M ammonium hydroxide (81 μl providing an N/C atomic ratio of 0.1), and pure water (1 ml). Paraformaldehyde was obtained from Alfa Aesar, and glycolaldehyde (dimer) was obtained from Sigma-Aldrich. Calcium hydroxide [Ca(OH)2] and ammonium hydroxide were obtained from Wako Pure Chemical. Paraformaldehyde hydrolyzed very rapidly at high pH to yield pure formaldehyde. Ca(OH)2 was added to make the starting solution with a pH in the range of 11.5 to 11.7, and Ca(OH)2 also acted as a catalyst of the formose reaction (5 (link), 28 , 51 (link)). Each solution charged into glass tubes that were flame-sealed and then heated isothermally at 90°, 150°, 200°, and 250°C for 72 hours in an oven (ETTAS HTO-450S). After heating, the residues were separated by centrifugation. Water used in this synthetic experiment and the following analytical procedures was purified with a Millipore Milli-Q system.
4
Purification and Enzyme Characterization
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Water
was purified using Milli-Q Academic
purification system. Q-Sepharose and Sephacryl S-200 were purchased
from GE Healthcare. Dowex 50WX4-200R (H+ form), nicotinamide
adenine dinucleotide reduced (NADH, disodium salt), dihydroxyacetone
phosphate hemimagnesium salt, glycolaldehyde dimer, 2-(N-morpholino)ethanesulfonic acid sodium salt (MES, ≥99.5%),
triethanolamine hydrochloride (TEA, ≥99.5%), ampicillin, kanamycin
sulfate, andd ,l -dithiothreitol (DTT) were purchased
from Sigma-Aldrich. Protease inhibitor tablets (Complete brand) and
bovine serum albumin, fraction V (BSA), were purchased from Roche.
Ammonium sulfate (enzyme grade), guanidinium hydrochloride (electrophoresis
grade, min. 99%), sodium hydroxide (1.0 N), and hydrochloric acid
(1.0 N) were purchased from Fisher. Sodium phosphite (dibasic, pentahydrate)
was purchased from Fluka, and its water content was reduced to Na2HPO3·0.4H2O as previously described.7 (link) Quikchange II Site-Directed Mutagenesis Kits
were purchased from Agilent Technologies, and λDE3 Lysogenization
Kits were purchased from Novagen. All other chemicals were reagent
grade or better and were used without further purification.
was purified using Milli-Q Academic
purification system. Q-Sepharose and Sephacryl S-200 were purchased
from GE Healthcare. Dowex 50WX4-200R (H+ form), nicotinamide
adenine dinucleotide reduced (NADH, disodium salt), dihydroxyacetone
phosphate hemimagnesium salt, glycolaldehyde dimer, 2-(N-morpholino)ethanesulfonic acid sodium salt (MES, ≥99.5%),
triethanolamine hydrochloride (TEA, ≥99.5%), ampicillin, kanamycin
sulfate, and
from Sigma-Aldrich. Protease inhibitor tablets (Complete brand) and
bovine serum albumin, fraction V (BSA), were purchased from Roche.
Ammonium sulfate (enzyme grade), guanidinium hydrochloride (electrophoresis
grade, min. 99%), sodium hydroxide (1.0 N), and hydrochloric acid
(1.0 N) were purchased from Fisher. Sodium phosphite (dibasic, pentahydrate)
was purchased from Fluka, and its water content was reduced to Na2HPO3·0.4H2O as previously described.7 (link) Quikchange II Site-Directed Mutagenesis Kits
were purchased from Agilent Technologies, and λDE3 Lysogenization
Kits were purchased from Novagen. All other chemicals were reagent
grade or better and were used without further purification.
5
Purification and Characterization of Enzyme
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Water was obtained from
a Milli-Q Academic
purification system. Q-Sepharose and Sephacryl S-200 were purchased
from GE Healthcare. Dowex hydrogen form, nicotinamide adenine dinucleotide,
reduced form (NADH, disodium salt), glycolaldehyde dimer, 2-(N-morpholino)ethanesulfonic acid sodium salt (MES, ≥99.5%),
triethanolamine hydrochloride (≥99.5%), and acetaldehyde were
purchased from Sigma-Aldrich. Ethylammonium chloride,d ,l -dithiothreitol (DTT), sodium hydroxide (1.0 N), and hydrochloric
acid (1.0 N) were purchased from Fisher Scientific. Sodium phosphite
dibasic form was purchased from Riedel de Haën. The λDE3
lysogenization kits were purchased from Novagen. All other chemicals
were reagent grade or better and were used without further purification.
a Milli-Q Academic
purification system. Q-Sepharose and Sephacryl S-200 were purchased
from GE Healthcare. Dowex hydrogen form, nicotinamide adenine dinucleotide,
reduced form (NADH, disodium salt), glycolaldehyde dimer, 2-(N-morpholino)ethanesulfonic acid sodium salt (MES, ≥99.5%),
triethanolamine hydrochloride (≥99.5%), and acetaldehyde were
purchased from Sigma-Aldrich. Ethylammonium chloride,
acid (1.0 N) were purchased from Fisher Scientific. Sodium phosphite
dibasic form was purchased from Riedel de Haën. The λDE3
lysogenization kits were purchased from Novagen. All other chemicals
were reagent grade or better and were used without further purification.
6
Hydrogenation of Sugars and Polyols
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Sucrose (SUC, 97 %), Maltose (MAL, 97 %), Mannose (MAN, 99 %), D‐Threitol (97 %) and Ammonium Metatungstate (AMT, 99.5 %) were purchased from Shanghai Aladdin Biochemical Technology Co., Ltd. Erythrose (ERO, 75 %), meso‐Erythtirol (99 %), Erythrulose (ERU, 85 %), 1,2‐propylene glycol (1,2‐PG, 98 %), Ammonium Phosphomolybdic (APM, AR) and Ammonium Paratungstate (APT, 99.5 %) were purchased from Shanghai Macklin Biochemical Technology Co., Ltd. Glycolaldehyde dimer (GA, 98 %), Glucose (GLU, 99.5 %), Fructose (99 %) and Ethylene glycol (EG, 99.8 %) were purchased from Sigma‐Aldrich. Mannitol (98 %) and Sorbitol (98 %) were purchased from Sinopharm Chemical Reagent Company. Ammonium tungsten oxide (AT, 99.9 %) was purchased from Alfa Aesar. Deionized water was produced by a laboratory water purification system. All other reagents were commercially available and were used as received.
The hydrogenation catalysts used in the investigation were Ru/C (5 % Ruthenium on activated carbon, Maclin), Pd/C (5 % Palladium on activated carbon, Aladdin) and Pt/C (5 % Platinum on activated carbon, Aladdin). XRD patterns of these catalysts indicated their small metal sizes (Figure S6).
The hydrogenation catalysts used in the investigation were Ru/C (5 % Ruthenium on activated carbon, Maclin), Pd/C (5 % Palladium on activated carbon, Aladdin) and Pt/C (5 % Platinum on activated carbon, Aladdin). XRD patterns of these catalysts indicated their small metal sizes (Figure S6).
7
Synthesis and Characterization of Carbohydrate Derivatives
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All chemicals used are commercially available and were used without further purification: glycerol (≥99.5%, Sigma-Aldrich), KOH (≥85%, Sigma-Aldrich), Ni(NO3)2•6H2O (Sigma-Aldrich), KNO3 (99%, Alfa Aesar), H3BO3 (99.8%, Alfa Aesar), K2SO4 (≥99.0%, Sigma-Aldrich), 1,3-dihydroxyacetone (Sigma-Aldrich, pharmaceutical standard), DL-glyceraldehyde (≥90%, Sigma-Aldrich), DL-glyceric acid (20% in water, TCI), glycolic acid (99%, Sigma-Aldrich), glycolaldehyde dimer (Sigma-Aldrich), oxalic acid (99.999%, Sigma-Aldrich), tartronic acid (97%, Thermo Scientific), sodium β-hydroxypyruvate hydrate (≥97.0%, Sigma-Aldrich), sodium mesoxalate monohydrate (≥98.0%, Sigma-Aldrich), sodium formate (≥99.0%, Sigma-Aldrich). Deionized water (Barnstead E-pure water purification system, resistivity >18 MΩ cm) was used to prepare all solutions.
8
Enzymatic Assay for Glycolate Oxidation
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Glycolaldehyde dimer, d -xylono-1,4-lactone, dl -lactaldehyde, d -xylonic acid lithium salt were purchased from Sigma-Aldrich UK. Zinc chloride was purchased from Merck, Germany. Mammalian hydroxyacid oxidase 1 (or glycolate oxidase, HAO1) enzyme was obtained from MyBioSource USA and LDH (lactate dehydrogenase) from rabbit muscle was purchased from Sigma-Aldrich. 10-Acetyl-3,7-dihydroxyphenoxazine (or Amplex Red) was purchased from Sigma-Aldrich. All other substrates were purchased from Sigma-Aldrich in high purity grade. The E. coli BL21(DE3) strain was used for the pBAT4 (Peränen et al. 1996 (link)) based cytoplasmic expression vectors. LB growth media was prepared according to Sambrook and Russel (2001 ). Glucose release medium EnPresso B was obtained from Bio-Silta Ltd. Ampicillin resistance (100 μg ml−1) was used for the selection of all plasmids. d -xylono-1,4-lactone was analysed by 1H-NMR spectroscopy to verify it has not spontaneously opened to d -xylonic acid.
9
Preparation of Aqueous Electrolyte Solutions
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All electrolytes were made
by dissolving appropriate amounts of chemicals in Milli-Q water (Millipore,
resistivity ≥ 18.2 MΩ cm). All chemicals were used without
any further purification: KOH (99.9%, Sigma-Aldrich), KHCO3 (>99.5%, Sigma-Aldrich), K2HPO4 (99.99%,
Merck),
KH2PO4 (99.99%, Merck), KMnO4 (ACS
reagent, Fluka), H2SO4 (ACS Reagent, Fluka),
H2O2 (35%, Merck), H3PO4 (Merck, 85%), formaldehyde (37% in water—contains 10–15%
methanol as a stabilizer, Sigma-Aldrich), acetaldehyde (>99.5%,
Sigma-Aldrich),
propionaldehyde (ACS reagent, Fluka), glyoxal (∼40% in H2O, Sigma-Aldrich), acetone (99.5%, Sigma-Aldrich), methanol
(99.9%, Merck), ethanol (Absolute, Thermo Fisher Chemical), 1-propanol
(99.99%, Sigma-Aldrich), glycolaldehyde dimer (>99.9%, Sigma-Aldrich),
ethylene glycol (99.8%, Sigma-Aldrich), 1,2-propanediol (>99.5%,
Sigma-Aldrich),
1,3-propanediol (98%, Sigma-Aldrich), glycerol (>99.5%, Sigma-Aldrich),
methylglyoxal (∼40% in H2O,Merck), hydroxyacetone
(95%, Alfa Aesar),dl -2-hydropropanal (∼1 M in H2O, Sigma-Aldrich), 3-hydroxypropanal (95%, MolPort), dl -glyceraldehyde (>97%, Sigma-Aldrich), and dihydroxyacetone (97%,
Sigma-Aldrich). Gases CO2 (Linde, 4.5), CO (Linde, 4.7),
and Ar (Linde, 5.0) were used as received.
by dissolving appropriate amounts of chemicals in Milli-Q water (Millipore,
resistivity ≥ 18.2 MΩ cm). All chemicals were used without
any further purification: KOH (99.9%, Sigma-Aldrich), KHCO3 (>99.5%, Sigma-Aldrich), K2HPO4 (99.99%,
Merck),
KH2PO4 (99.99%, Merck), KMnO4 (ACS
reagent, Fluka), H2SO4 (ACS Reagent, Fluka),
H2O2 (35%, Merck), H3PO4 (Merck, 85%), formaldehyde (37% in water—contains 10–15%
methanol as a stabilizer, Sigma-Aldrich), acetaldehyde (>99.5%,
Sigma-Aldrich),
propionaldehyde (ACS reagent, Fluka), glyoxal (∼40% in H2O, Sigma-Aldrich), acetone (99.5%, Sigma-Aldrich), methanol
(99.9%, Merck), ethanol (Absolute, Thermo Fisher Chemical), 1-propanol
(99.99%, Sigma-Aldrich), glycolaldehyde dimer (>99.9%, Sigma-Aldrich),
ethylene glycol (99.8%, Sigma-Aldrich), 1,2-propanediol (>99.5%,
Sigma-Aldrich),
1,3-propanediol (98%, Sigma-Aldrich), glycerol (>99.5%, Sigma-Aldrich),
methylglyoxal (∼40% in H2O,Merck), hydroxyacetone
(95%, Alfa Aesar),
Sigma-Aldrich). Gases CO2 (Linde, 4.5), CO (Linde, 4.7),
and Ar (Linde, 5.0) were used as received.
10
Biomass Conversion to Biofuels
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The cellulose (99%) used in the experiments was purchased from VWR. Glucose (99%)
and fructose (99%) used as starting biomass in the experiments were purchased from Sigma.
Wheat bran was supplied by a local supplier. Distilled water was used as reaction medium in the experiments. The standards used in HPLC (High Performance Liquid Chromatography) analysis were: cellobiose (+98%), Glucose (+99%), fructose (+99%), glyceraldehyde (95%), pyruvaldehyde (40%), glycolaldehyde dimer (99%), levulinic acid (+99%), 5-HMF (99%) purchased from Sigma.
and fructose (99%) used as starting biomass in the experiments were purchased from Sigma.
Wheat bran was supplied by a local supplier. Distilled water was used as reaction medium in the experiments. The standards used in HPLC (High Performance Liquid Chromatography) analysis were: cellobiose (+98%), Glucose (+99%), fructose (+99%), glyceraldehyde (95%), pyruvaldehyde (40%), glycolaldehyde dimer (99%), levulinic acid (+99%), 5-HMF (99%) purchased from Sigma.
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