D allose

Manufactured by Merck Group

Sourced in United States

D-allose is a rare sugar that functions as a monosaccharide. It is used in laboratory settings as a reference standard and analytical tool for research and development purposes.

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Lab products found in correlation

12 protocols using d allose

Characterization of Polysaccharide Structures

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d-(+)-Glucose, d-allose, d-galactose, Ag₂CO₃, L-cysteine methyl ester hydrochloride, phenyl isothiocyanate, pyridine, iPrOH, MTBE, porcine pancreatic α-amylase, acarbose, dinitrosalicylic acid, ACN and MeOH HPLC grade, and n-hexane, CHCl₃, MeOH, ACN, (CH₃)₂CO and EtOAc technical grade were purchased from Sigma-Aldrich (St. Louis, MO, USA). Nano-pure water HPLC grade (18.2 MΩcm) was obtained from a NANO pure purification system (Barnstead/Thermolyne, Dubuque, IA, USA). Silica gel 60 F254 TLC plates, HCl and H₃PO₄ were purchased from EMD Millipore, Inc. (Darmstadt, Germany). Silica gel 60 Å 40-63 µm and AcOH glacial were purchased from VWR International LLC (West Chester, PA, Switzerland), while RP-C₁₈ Cosmosil 140 and formic acid were purchased from Nacalai Tesque, Inc., (Kyoto, Japan) and Alfa Aesar (Ward Hill, MA, USA), respectively. MeOH and pyridine NMR (perdeuterated) solvents were purchased from Cambridge Isotope Laboratories (Andover, MA, USA).

Perera W.H., Shivanagoudra S.R., Pérez J.L., Kim D.M., Sun Y., K. Jayaprakasha G, & S. Patil B. (2021). Anti-Inflammatory, Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of Momordica charantia L.. Molecules, 26(4), 1038.

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Enzymatic Synthesis of Sugar Lactones

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All
chemicals and buffers were purchased
from Sigma-Aldrich, unless otherwise specified. Sugar lactones that
were not commercially available were synthesized according to standard
published procedures with the exception of 4-deoxy-l-fucono-1,5-lactone,
which was enzymatically synthesized.^{13 (link),14 (link)} The noncommercial
lactones included the following: l-fucono-1,4-lactone, d-arabinono-1,4-lactone, l-xylono-1,4-lactone, l-mannono-1,4-lactone, d-talono-1,4-lactone, d-allono-1,4-lactone, l-rhamnono-1,4-lactone, d-lyxono-1,4-lactone, l-lyxono-1,4-lactone, l-arabinono-1,4-lactone, d-xylono-1,4-lactone, l-mannono-1,5-lactone, l-rhamnono-1,5-lactone, and 4-deoxy-l-fucono-1,5-lactone.
The sugar lactones that were obtained from either CarboSynth or ChromaDex
included the following compounds: l-galactono-1,4-lactone, d-mannono-1,4-lactone, d-galactono-1,4-lactone, d-ribono-1,4-lactone, d-glucurono-6,3-lactone, d-erythronolactone, and l-glucono-1,5-lactone. Aldose
sugars were obtained from either Sigma-Aldrich or Carbosynth and included l-fucose, l-galactose, l-glucose, d-altrose, d-arabinose, l-xylose, l-rhamnose, d-mannose, l-allose, d-talose, l-talose, d-allose, d-galactose, l-mannose, d-gulose, d-glucose, l-arabinose, l-ribose, d-lyxose, l-lyxose, d-xylose, d-ribose,
and 4-deoxy-l-fucose.

Hobbs M.E., Williams H.J., Hillerich B., Almo S.C, & Raushel F.M. (2014). l-Galactose Metabolism in Bacteroides vulgatus from the Human Gut Microbiota. Biochemistry, 53(28), 4661-4670.

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Comprehensive Carbohydrate Analysis Protocol

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All foods and food products were purchased from local markets (Davis and Sacramento, CA, USA) including Safeway, Trader Joe’s, Davis Food Co-op, Whole Foods, Nugget Markets, Target, and online (Amazon). Trifluoroacetic acid (TFA, HPLC grade), 3-methyl-1-phenyl-2-pyrazoline-5-one (PMP), chloroform (HPLC grade), ammonium hydroxide solution (NH₄OH) (28–30%), ammonium acetate, sodium acetate, glacial acetic acid, methanol (HPLC grade), D-fructose, D-mannose, D-allose, D-glucose, D-galactose, L-rhamnose, L-fucose, D-ribose, D-xylose, L-arabinose, N-acetyl-D-glucosamine (GlcNAc), N-acetyl-D-galactosamine (GalNAc), D-glucuronic acid (GlcA), and D-galacturonic acid (GalA) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Arabinoxylan and polygalacturonic acid were purchased from Megazyme (Bray, Ireland). 96-well Nunc plates and lids were purchased from Thermo Scientific. Viscozyme was provided by Novozyme (Davis, CA, USA). Acetonitrile (ACN) (HPLC grade) was purchased from Honeywell (Muskegon, MI, USA). Nanopure water was used for all experiments.

Castillo J.J., Couture G., Bacalzo NP J.r., Chen Y., Chin E.L., Blecksmith S.E., Bouzid Y.Y., Vainberg Y., Masarweh C., Zhou Q., Smilowitz J.T., German J.B., Mills D.A., Lemay D.G, & Lebrilla C.B. (2022). The Development of the Davis Food Glycopedia—A Glycan Encyclopedia of Food. Nutrients, 14(8), 1639.

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Comprehensive Glycan Analysis Protocol

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Sodium acetate, hydrogen peroxide (H₂O₂) (30% v/v), iron(III)
sulfate pentahydrate (Fe₂(SO₄)₃), trifluoroacetic acid
(TFA) (HPLC grade), chloroform (HPLC grade), ammonium acetate, sodium hydroxide pellets
(semiconductor grade 99.99% trace metals basis), ammonium hydroxide solution
(NH₄OH) (28–30%), 3-methyl-1-phenyl-2-pyrazoline-5-one (PMP),
dichloromethane (DCM), methanol (HPLC grade), anhydrous dimethyl sulfoxide (DMSO), glacial
acetic acid, d-galactose, d-mannose, d-glucose,
d-allose, d-fructose, d-xylose, l-arabinose,
d-xylose, l-fucose, l-rhamnose,
N-acetyl-d-glucosamine (GlcNAc),
N-acetyl-d-galactosamine (GalNAc), d-glucuronic acid
(GlcA), and d-galacturonic acid (GalA) were purchased from Sigma-Aldrich (St.
Louis, MO). Maltotriose, maltotetraose, maltopentaose, and maltohexaose were obtained from
Carbosynth (Compton, UK). Galactan was purchased from Megazyme (Bray, Ireland). C18 and
porous graphitized carbon (PGC) solid phase extraction (SPE) plates were purchased from
Glygen (Columbia, MD). Formic acid (FA) (99.5% optima LC/MS grade) was purchased from
Fisher Scientific (Hampton, NH). Acetonitrile (ACN) (HPLC grade) was purchased from
Honeywell (Muskegon, MI). All purchased chemicals were used without further purification.
Butternut squash was purchased from Pedrick Produce (Dixon, CA). Nanopure water was used
for all experiments.

Castillo J.J., Galermo A.G., Amicucci M.J., Nandita E., Couture G., Bacalzo N., Chen Y, & Lebrilla C.B. (2021). A Multidimensional Mass Spectrometry-Based Workflow for De Novo Structural Elucidation of Oligosaccharides from Polysaccharides. Journal of the American Society for Mass Spectrometry, 32(8), 2175-2185.

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Immobilized Streptomyces murinus GI Biocatalysis

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Food-grade immobilized GI from Streptomyces murinus (Sweetzyme IT) was purchased from Novozyme (Kalubdborg, Denmark). D-allose, D-allulose, and other reagents were purchased from Sigma Aldrich (St. Louis, MO, United States). The packed bed reactor XK26/100 was purchased from GE Healthcare Life Science (Uppsala, Sweden).

Choi M.N., Shin K.C., Kim D.W., Kim B.J., Park C.S., Yeom S.J, & Kim Y.S. (2021). Production of D-Allose From D-Allulose Using Commercial Immobilized Glucose Isomerase. Frontiers in Bioengineering and Biotechnology, 9, 681253.

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Monosaccharide Isolation from Novel Compounds

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The new compounds 3, 4, 6 and 7 (2 mg of each) were dissolved in MeOH (2 mL) and refluxed with 1.0 N HCl (2 mL) for 3 h and following by extracting with ethyl acetate. The water layer was then neutralized by Ag₂CO₃, and filtered to give a monosaccharide. Each monosaccharide of those compounds had an Rf (n-BuOH–AcOH–H₂O, 4:1:1) and specific rotation [α]d + 52.7° (c 0.10, H₂O); [α]d + 24.3° (c 0.10, H₂O); [α]d + 14.4° (c 0.05, H₂O) corresponding to those of d-glucose, d-xylose and d-allose (Sigma-Aldrich, St. Louis, MO, USA), respectively.

Huyen C.T., Luyen B.T., Khan G.J., Oanh H.V., Hung T.M., Li H.J, & Li P. (2018). Chemical Constituents from Cimicifuga dahurica and Their Anti-Proliferative Effects on MCF-7 Breast Cancer Cells. Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry, 23(5), 1083.

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Longan Fruit Chemical Composition

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Fresh longan fruits cultivar Edor with size code 2 (more than 2.2–2.5 cm in diameter) was purchased from a local market in Lamphun province in 2019. A standard solution of amino acids mixture (type H), which contained 17 common amino acids (e.g., Asp-aspartic acid, Thr-threonine, Ser-serine, Glu-glutamic acid, Pro-proline, Gly-glycine, Ala-alanine, Cys-cysteine, Val-valine, Met-methionine, Ile-isoleucine, Leu-leucine, Tyr-tyrosine, Phe-phenylalanine, His-histidine, Lys-lysine and Arg-arginine) was purchased from Wako Pure Chemical Corporation, Osaka, Japan. Eight types of sugar standards used for analysis were D-psicose, D-glucose, D-fructose, D-xylose, D-rhamnose, D-allose, D-mannose, and sucrose (Sigma-Aldrich Singapore, Singapore). HPLC grade methanol and acetonitrile were purchased from RCI, Labscan, Bangkok, Thailand. All solutions and dilutions were performed using deionized water, which was generated using a Milli-Q water system (Zeneer up 900, Seoul, Korea).

Somjai C., Siriwoharn T., Kulprachakarn K., Chaipoot S., Phongphisutthinant R, & Wiriyacharee P. (2021). Utilization of Maillard reaction in moist-dry-heating system to enhance physicochemical and antioxidative properties of dried whole longan fruit. Heliyon, 7(5), e07094.

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Metabolic Modulation in Cancer Research

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BML275 (water-soluble) and Imatinib were obtained from Santa Cruz Biotechnology and LC Laboratories, respectively. Stock solutions were prepared in DMSO or sterile water at 10 mmol/L and stored at −20°C. Prednisolone and dexamethasone (water-soluble) were purchased from Sigma-Aldrich and were resuspended in ethanol or sterile water at 10 mmol/L, respectively. Stock solutions were stored at −20°C. Fresh solutions (pH adjusted) of methyl pyruvate (MP), oxaloacetate (OAA), 3-O-methylglucose (3-OMG; an agonist of TXNIP), D-allose (an agonist of TXNIP) and recombinant insulin (Sigma-Aldrich) were prepared for each experiment. Dimethyl succinate (DMS) was obtained from Acros Organics, and fresh solutions (pH adjusted) were prepared prior to each experiment. For competitive growth assays, 5 mmol/L methyl pyruvate (MP), 5 mmol/L Dimethyl succinate (DMS) and 5 mmol/L oxaloacetate (OAA) were used. CNR2 agonist HU308 was obtained from Cayman Chemical.

Chan L.N., Chen Z., Braas D., Lee J.W., Xiao G., Geng H., Cosgun K.N., Hurtz C., Shojaee S., Cazzaniga V., Schjerven H., Ernst T., Hochhaus A., Kornblau S.M., Konopleva M., Pufall M.A., Cazzaniga G., Liu G.J., Milne T.A., Koeffler H.P., Ross T.S., Sanchez-Garcia I., Borkhardt A., Yamamoto K.R., Dickins R.A., Graeber T.G, & Müschen M. (2017). Metabolic gatekeeper function of B-lymphoid transcription factors. Nature, 542(7642), 479-483.

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Infant Gut Glycan Profiling

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d-Glucose, d-galactose, d-mannose, d-allose, d-fructose, N-acetyl-d-glucosamine (GlcNAc), N-acetyl-d-galactosamine (GalNAc), d-arabinose, d-xylose, d-ribose, L-rhamnose, L-fucose, d-glucuronic acid (GlcA), d-galacturonic acid (GalA), N-acetylneuraminic acid (Neu5Ac), N-glycolylneuraminic acid (Neu5Gc), d-apiose, d-talose, d-altrose, L-gulose, d-glucosamine hydrochloride (GlcN), d-galactosamine hydrochloride (GalN), d-mannosamine (ManN), N-acetyl-d-mannosamine (ManNAc), ammonium acetate, PMP, ammonia (28.0-30.0%), and chloroform were purchased from Sigma-Aldrich (St. Louis, MO). d-Lyxose was purchased from TCI America (Portland, OR). Acetonitrile (LC-MS grade) was purchased from Honeywell (Muskegon, MI). Five fecal samples from the same infant were collected after the infant was fed with different diets including breast milk only (sample 1 and sample 3), breast milk with water (sample 2), breast milk with squash (sample 4), and squash only (sample 5). All five samples were collected within a two-week period at six months postpartum.

Xu G., Amicucci M.J., Cheng Z., Galermo A.G, & Lebrilla C.B. (2017). Revisiting Monosaccharide Analysis – Quantitation of a Comprehensive Set of Monosaccharides using Dynamic Multiple Reaction Monitoring. The Analyst, 143(1), 200-207.

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Chromatographic Analysis of Phytochemicals

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Standards for chromatography analyzes (ferulic acid, chlorogenic acid, caffeine, monosaccharides, D-allose) were obtained from Sigma-Aldrich (St. Louis, MO, USA), except protocatechuic acid, trigonelline (USP, São Paulo, Brazil) and D-(+)-xylose (Supelco, Bellefonte, PA, USA).

Cangussu L.B., Melo J.C., Franca A.S, & Oliveira L.S. (2021). Chemical Characterization of Coffee Husks, a By-Product of Coffea arabica Production. Foods, 10(12), 3125.

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