PEG-thioester-norbornene, PEG-ester-norbornene, and PEG-amide-norbornene microgels were labeled with 20 μM Alexa Fluor 546 C, 20 μM Dylight 405 Maleimide, 20 μM and fluorescein-maleimide respectively to visualize the individual microgel chemistries. Microgels were mixed 3:1:1 amide:thioester:ester by volume (2:1:1 mixtures with a degraded fraction of 0.5 resulted in unstable scaffolds that failed to consistently maintain overall filament integrity), and were prepared for 3D printing by swelling microgels with photostiffening solution for 10 minutes at 4°C, pelleting by centrifugation at 4,000 rcf for 5 minutes, and aspirating the supernatant. The microgel pellet was loaded into a 1 mL syringe with a gel spatula. The mixed microgel populations were printed into a multiwell glass-bottom plate, photostiffened for 2.5 minutes with 2.5 mW/cm2 365 nm light, and swollen in PBS. Logic gated degradation of microgel scaffolds was visualized by fluorescence microscopy (Movie S4 ). Thioester microgels were degraded by adding 5 mM L-cysteine methyl ester (Sigma), 10% sucrose (Sigma) in PBS, pH 7.4 to the printed constructs. Ester microgels were degraded by adding 20 mM NaOH (Sigma) in PBS, pH 12 to the printed constructs. Microgels were degraded overnight in a humidified chamber at 37°C.
L cysteine methyl ester
Manufactured by Merck Group
Sourced in Germany
L-cysteine methyl ester is a chemical compound used in various laboratory applications. It is a derivative of the amino acid L-cysteine, where the carboxyl group has been replaced with a methyl ester group. This compound is commonly used as a precursor or building block in organic synthesis and pharmaceutical research.
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Lab products found in correlation
L glucose, by Merck Group (2 mentions)
Sucrose, by Merck Group (1 mentions)
Sodium hydroxide (naoh), by Merck Group (1 mentions)
Xanthohumol, by Merck Group (1 mentions)
Quercetin 3 o rhamnoside, by Merck Group (1 mentions)
D galactose, by Merck Group (1 mentions)
L galactose, by Merck Group (1 mentions)
O tolyl isothiocyanate, by Merck Group (1 mentions)
Kaempferol 3 o rutinoside, by Merck Group (1 mentions)
D glucose, by Merck Group (1 mentions)
Pyridine, by Merck Group (1 mentions)
Phenylisothiocyanate, by Thermo Fisher Scientific (1 mentions)
Kinetex c8 column, by Phenomenex (1 mentions)
Uv 1800 uv vis spectrophotometer, by Shimadzu (1 mentions)
3 protocols using l cysteine methyl ester
1
Engineered Microgel Scaffolds for 3D Printing
2
Analytical Standards for Phytochemical Analysis
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ACS-grade methanol for extraction, LC-MS OptimaTMacetonitrile, and UHPLC-MS/MS OptimaTM grade solvents (water, acetonitrile, methanol) were from Fisher (Thermo Fisher Scientific, Nepean, ON, Canada). SupraPurTM formic acid (98%–100%) and ACS grade isopropyl alcohol were from VWR (VWR International LLC, Mississauga, ON, Canada). Commercially available analytical standards were sourced from Extrasynthese (Genay, Cedex, FR) (quercetin-3-O-glucoside ≥ 99%; kaempferol-3-O-rutinoside ≥ 98%; quercetin-3-O-rhamnoside ≥ 98.5%) or Sigma-Aldrich (St. Louis, MO, USA) (quercetin-3-O-rutinoside ≥ 95%; kaempferol-3-O-glucoside ≥ 97%; xanthohumol ≥ 96%; quercetin-3-O-(6’’-O-malonyl)-glucoside ≥ 85%). International Calibration Extract 3 (ICE-3), an alpha & beta acid standardized mixture, was sourced from Labor Veritas (AG, Zurich, CZ). Deuterated solvent (DMSO-d6) was from CIL (Cambridge Isotope Laboratories Inc., Tewksbury, MA, USA). Pyridine, o-tolyl isothiocyanate, L-cysteine methyl ester, D-glucose, L-glucose, D-galactose, L-galactose were purchased from Sigma-Aldrich.
3
Analysis of Varlaxin Natural Products
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D-and L-Glucose were purchased from Sigma-Aldrich. Hydrolysis of varlaxin 1022A and sample derivatizations were performed as previously described 37 with the following exceptions: approximately 0.4 mg of varlaxin 1022A was hydrolysed, freeze dried instead of drying under N 2 gas stream, and the reagents L-cysteine methyl ester (Sigma-Aldrich) and o-tolyl isothiocyanate (Thermo Fisher GmbH, Germany) instead of phenyl isothiocyanate were added simultaneously, and the reaction mixture was incubated at 60 °C for 1 h and diluted with MeOH before UPLC-QTOF analysis. Samples of 1 µL were analysed with two LC methods. The sample was injected into a Kinetex C8 column (50 or 100 × 2 mm, 1.7 μm, Phenomenex Inc.), which was eluted at 0. The 13 C HMBC experiment (for observing long-range 1 H-13 C connectivity) was measured using n J CH transfer time optimized for 8 Hz couplings. For monosaccharide analysis, varlaxin 1046A was hydrolysed for 1 h at 100 °C in 0.5 mL of 2 M D 2 SO 4 in D 2 O. The proton spectrum was collected, and anomeric signals were compared with data from a previous publication. 38 UV spectra of varlaxins 1022A and 1046A, and a reference compound 4-hydroxyphenylacetic acid were measured in MeOH with a UV-1800 UV-Vis spectrophotometer (Shimadzu, Kyoto, Japan).
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