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4 protocols using methanol d4

1

Preparation and NMR Characterization of Phosphate Buffers

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All chemicals and reagents used were of analytical grade. Potassium dihydrogen phosphate (99%, KH2PO4), deuterium oxide (99.9%, D2O), methanol-d4 (>99.8%, MeOD), and methanol were purchased from VWR (Radnor, PA, United States). Sodium deuteroxide 40% w/v solution in D2O (99.5%, NaOD) was obtained from Alfa Aesar (Kandel, Germany). 3-(Trimethylsilyl) propionic-2,2,3,3-d4 acid sodium salt (99%, TMSP) was obtained from Sigma-Aldrich (St. Louis, MO, United States). A Millipore Direct-Q® 3 UV Water Purification System (Millipore Corp., Bedford, MA, United States) or (Merck KGaA, Darmstadt, Germany) for ultrapure water was used throughout the study.
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2

Metabolite Profiling of Plantago and Forsythia

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The underground organs of three Plantago species (P. lanceolata L., P. major L., and P. media L.) were collected from different Hungarian locations in June of 2018. Leaf and fruit samples of the Forsythia species (F. europaea Degen & Bald, F. suspensa Vahl, and F. × intermedia cultivars ‘Lynwood’, ‘Melisa’, ‘Minigold’, ‘Primulina’, ‘Spectabilis’, and ‘Week End’) were collected from the Botanical Garden of Szent István University (Budapest, Hungary, Villányi street 29–43): the leaves and unripe, green fruits in July of 2018 and the ripe, yellow-brown, closed fruits as well as the ripe, yellow-brown, opened fruits in October of 2018. The collected samples were immediately lyophilized on the day of collection. The voucher specimens of all dried samples are deposited in the Department of Plant Anatomy, Eötvös Loránd University, Budapest, Hungary. The materials and reagents applied in the analysis and isolation of plant metabolites, such as acetonitrile (ACN), distilled water (DW), formic acid, dimethyl sulfoxide (DMSO), methanol (Reanal, Budapest, Hungary), DMSO-d6, and methanol-d4 (VWR chemicals, Leuven, Belgium) were all of analytical reagent grade of the highest purity available.
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3

Deuterated Reagents for NMR Spectroscopy

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Methanol-d4 (CD3OD, 99.8 D-%) and deuterium oxide (D2O, 99.96 D-%) were acquired from VWR International Oy (Espoo, Finland). The 3-(trimethylsilyl)propionic-2,2',3,3'-d4 acid sodium salt (TSP, 98 D-%) was acquired from Sigma-Aldrich (St. Louis, MO).
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4

Synthesis and Characterization of Functionalized Polymers

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ABDV was from Wako Chemicals GmbH (Neuss,
Germany). EGDMA and ARS were from Acros Organics. 4-Vinylphenylboronic
acid (FM3), ammonium hydrogen difluoride (NH4HF2), acetic acid, acetic anhydride, phenol, ammonium acetate, formic
acid, dimethylformamide (DMF), dry methanol (MeOH), DMSO-d6, and methanol-d4 (CD3OD) were
from VWR chemicals. All solvents for high-performance liquid chromatography
(HPLC) analysis were of HPLC grade and were purchased from VWR. 2-Aminoethyl
methacrylate hydrochloride (FM2) was received from Polysciences. Amino-functionalized
macroporous silica beads (NH2@SiO2) with an
average particle size of 30 μm, a surface area (S) of 45 m2g–1, an average pore diameter (Dp) of 47.5 nm, and a pore volume (Vp) of 0.81 mL/g were purchased from Fuji Silysia Chemical Ltd.
(Kozojicho, Kasugai Aichi, Japan). Monosaccharides Glc, galactose
(Gal), Fru, and TBA hydroxide (TBA–OH) 1 M in methanol were
obtained from Sigma-Aldrich. D-GlcA was received
from Fluka. N-Acetylneuraminic acid, N-glycolylneuraminic acid (Neu5Gc), GalNAc, ManNac, 2,6′-sialyllactose
sodium salt (6SL), and 2,3′-sialyllactose sodium salt (3SL)
were purchased from Carbosynth Ltd. (UK).
EGDMA was passed through
a column of activated basic alumina to remove the inhibitor and stored
at −20 °C before polymerization. N-3,5-Bis(trifluoromethyl)-phenyl-N′-4-vinylphenylurea (FM1) was synthesized as previously
reported.33 (link)
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