Anhydrous magnesium sulfate

2,3,4,5,6-Pentafluorobenzyl bromide (Fluorochem,
99%) and acrylic acid (Sigma-Aldrich, 99%) were used as received.
Acetone (Sigma-Aldrich, ≥99%) was stored with molecular sieves
(3 Å, Sigma-Aldrich) to make it anhydrous prior to use. Diethyl
ether (≥99.8%), n-butyl acrylate (BA, ≥99%),
and methanol (≥99.9%) were purchased from Sigma-Aldrich and
used as received. Potassium carbonate (anhydrous, ≥99%), sodium
bicarbonate (≥99.7%), anhydrous magnesium sulfate, acetonitrile
(≥99.8%), chloroform (≥99.8%), and tetrahydrofuran (THF,
chromatography GPC grade) were obtained from Fisher Scientific. Sodium
azide (99%) and N,N-dimethylformamide
(DMF, dried over molecular sieves, 99.8%) were purchased from Acros
Organics and used as received. chloroform-D (CDCl₃, 99.8%,
+0.05% v/v TMS) was obtained from Cambridge Isotope Laboratories,
Inc. Azobisisobutyronitrile (AIBN, Sigma-Aldrich, 98%) was recrystallized
from methanol and dried at room temperature prior to storage in a
freezer. 4-Chloro-7-nitro-2,1,3-benzoxadiazole (NBD chloride, 98%)
and piperazine (99%) were purchased from Sigma-Aldrich and Fluorochem,
respectively. Two commercial polyacrylate copolymer PSAs (referred
to hereafter as P1 and P2), which were used as a benchmark in this
work, were provided by Synthomer plc.

Tetrahydrofuran (THF, HPLC grade), dimethyl sulfoxide (DMSO, HPLC grade), dichloro-methane (DCM, HPLC grade), diglycolic anhydride (97%, Alfa Aesar, Haverhill, MA, USA), diisopropylcarbodiimide (99%, Alfa Aesar, Haverhill, MA, USA), alcohol-free chloroform, acetonitrile (HPLC grade), ethanol (ACS reagent grade), methanol (ACS reagent trade), 4-(dimethylamino)pryridine (99%), anhydrous magnesium sulfate, and acetic acid (ACS reagent grade) were purchased from Fisher Scientific (Pittsburg, PA, USA). Hydrochloric acid (37%, 12 M, ACS grade), tannic acid (TA) (ACS grade), iron (III) chloride hexahydrate (97%), α-tocopherol (vitamin E, >95.5%), pyridine (anhydrous, 99.8%), deuterated chloroform CDCl₃, and anhydrous sodium acetate were purchased from Sigma-Aldrich (St. Louis, MO, USA). Paclitaxel (PTX, >98%) and lapatinib (LAP, >98%) were obtained from Cayman Chemical Company (Ann Arbor, MI, USA); phosphate buffered saline without calcium and magnesium was purchase from Lonza (Basel, Switzerland). Polystyrene-b-polyethylene glycol (1600-b-5000 g/mol) (PS-b-PEG) was obtained from Polymer Source (Montreal, QC, Canada) and was purified by dissolving in THF (~40 °C) and precipitating into diethyl ether then dried by vacuum for two days as previously described [65 (link)].

Ferulic acid, 1 M diisobutyl aluminum hydride in dichloromethane, benzyl bromide, laccase from Trametes versicolor (776 U/g), piperazine, and sodium hydride were purchased from Sigma-Aldrich and used as received. Acetovanillone, sodium borohydride, pyridine, and diethylcarbonate were purchased from TCI and used as received. Palladium on carbon and anhydrous magnesium sulfate were purchased from Acros Organics and used as received. Deuterated solvents were purchased from Euriso-top. Other reagents, salts, and solvents were purchased from VWR.
DMF was dried using mBraun SPS 800. Evaporations were conducted under reduced pressure (Vario Vacuubrand pump) on Buchi R300. Flash chromatographies were performed on a Puriflash 4100 (Interchim) equipped with and pre-packed INTERCHIM PF-30SI-HP (30 μm silica gel) columns. IR analyses were performed on Cary 630 FTIR (Agilent). NMR analyses were recorded on a Bruker Fourier 300. ¹H NMR spectra of samples were measured on a 300 MHz apparatus, chemicals shifts were reported in parts per million relative to solvent residual peak (CDCl₃ δ = 7.26 ppm; DMSO-d₆ δ = 2.50 ppm). ¹³C NMR spectra of samples were recorded at 75 MHz and calibrated on solvent peak (CDCl₃ δ = 77.16 ppm; DMSO-d₆ δ = 39.52 ppm).

AAPH (2,2′-azobis (2-amidinopropane)) (Acros Organics), sodium phosphate dibasic, sodium chloride, potassium dihydrogen phosphate, potassium sulphate, TRIS (ultrapure), glycine (proteomics grade), ortho-boric acid, and methanol (HPLC grade) were obtained from VWR International Eurolab S.L. (Barcelona, Spain). Trizma^® base, ABTS (2,2′-azinobis (3-ethylbenzothiazoline 6-sulfonic acid)), DTT (DL-Dithiothreitol), Trolox^® (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid), fluorescein sodium salt, formic acid (reagent grade ≥ 95%), and diatomaceous earth (Hyflo^® Super Cel^®) were provided by Sigma-Aldrich (Steinheim, Germany). Sodium hydroxide, glacial acetic acid, and sulfuric acid were supplied by Fisher Scientific (Madrid, Spain). SDS (sodium dodecyl sulfate) and nitric acid (65% p/p) were purchased from Panreac (Barcelona, Spain). Bromophenol blue indicator (ACS reagent), acetonitrile (HPLC grade), trifluoroacetic acid, acetone, and glycerol were provided by Merck (Darmstadt, Germany). Absolute ethanol was obtained from J.T. Baker (Deventer, The Netherlands), Octadecyl C18 sorbent was obtained from Phenomenex (Madrid, Spain), and anhydrous magnesium sulfate (99.5% min powder) was obtained from Alfa Aesar (Karlsruhe, Germany). Deionized water with a resistivity of >18 MΩ/cm was obtained through a Milli-Q SP^® Reagent Water System (Millipore Corporation Bedford, MA, USA).