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2 protocols using milli q biocel a10 purification unit

1

Synthesis and Characterization of Lipid Compounds

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Myristic acid (Fluka Chemistry, 98%), palmitic acid (Riedel-de HaënTM, 98%), stearic acid (Sigma-Aldrich, 98.5%), oleic acid (Sigma-Aldrich, 99%), linoleic acid (Sigma-Aldrich, 99%), O-(1H-6-chlorobenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HCTU, Novabiochem), Nile red (Carl Roth), pyrene (Alfa Aesar, 98%), samarium(iii) acetate hydrate (Sigma-Aldrich, 99.9%), sodium thiosulfate (Sigma-Aldrich, 99%), N,N-diisopropylethylamine (DIPEA, Sigma-Aldrich, 99.5%), N,N-dimethylformamide (DMF, VWR chemicals, 99.9%), tetrahydrofuran (Acros organics, 99.6%), diethyl ether (VWR international, 100%), acetone (VWR international, 99%), acetonitrile (VWR international, 99.95%), formic acid (Thermo Fisher Scientific, 99%), methanol (VWR international, 100%), hydrogen peroxide (Acros organics, 35 wt% solution in water), toluene (VWR international, 100%), trifluoroacetic acid (Sigma-Aldrich, 99%), acetic acid (Sigma-Aldrich, 99.8%), phosphate buffer saline 10× (PBS 10×, Euromedex) were used without further purification. Ultrapure water (18 MΩ cm) was obtained by passing in-house deionized water through a Millipore Milli-Q Biocel A10 purification unit. Bacto Tryptone (Sigma), yeast extract (Sigma), ampicillin (Sigma) and isopropyl β-d-thiogalactopyranoside (IPTG, VWR chemicals) were used for cell culture.
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2

Clickable Glycoconjugate Synthesis Protocol

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Bacto-tryptone and yeast extract were obtained from Biokar Diagnostics (FR). LB medium was purchased from Sigma-Aldrich (FR). Ampicillin was purchased from Eurobio (FR). Glycerol and isopropyl β-D-thiogalactopyranoside (IPTG) were purchased from Euromedex (FR).
Glycidyl propargyl ether was obtained from Sigma-Aldrich (Saint-Quentin-Fallavier, FR).
Glacial acetic acid, Trizma® and Hexafluoroisopropanol (HFIP) were obtained from Sigma-Aldrich (FR). Deionized water (18 MΩ-cm) was obtained by using a Millipore Milli-Q Biocel A10 purification unit. Cuprisorb was purchased from Seachem. Ethanol (96.0%, EtOH), mEthanol (98.5%, MeOH) and acetonitrile (99.9%, ACN) were obtained from VWR international. NaCl (99%) was purchased from Alfa Aesar (FR). Azide monosaccharides (β-Dgalactopyranosyl azide, Gal-N 3 ; and β-D-glucopyranosyl azide (Glu-N 3 ) were obtained from Carbosynth (UK). Ammonium Acetate and Ammonium pyrrolidinedithiocarbamate, APDC, were purchased from Fisher Scientific (FR). RCA 120 and RCA 120 -Fluorescein were purchased from Eurobio (FR). Human serum from human male AB plasma, USA origin, sterile-filtered, was used as received from Sigma-Aldrich (FR). N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDETA) was purchased from Sigma-Aldrich (FR). CuSO 4 •5H 2 O was obtained from VWR (FR). Sodium ascorbate was obtained from Fisher Scientific (FR).
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