Diisopropylcarbodiimide

The peptoid and peptide synthesis reagents, including bromoacetic acid, diisopropylcarbodiimide, N-methylmorophiline, methylamine, isobutylamine, and piperidine were purchased from Sigma Aldrich. Solvents and various other reagents including triethylamine, acetic anhydride, dimethylformamide (DMF), trifluoroacetic acid (TFA), triispropylsilane, diethylether, and standard biochemical reagents were purchased from Fisher Scientific. Fmoc-Gly-OH, hexafluorophosphate benzotriazole tetramethyl uronium, dichlormethane (DCM), and Fmoc-MBHA rink amide resin were purchased from VWR. The MTase-Glo methyltransferase assay kit was purchased from Promega for completing kinetic analyses. PRMT1 and PRMT5 were expressed and purified as previously described (49 (link)).

All solvents and chemicals were used without any further purification and purchased as peptide grade when available. N-methylpyrrolidinone was purchased from Biosolve. Diisopropylcarbodiimide and collidine were purchased from Sigma. The following L-amino acids were used: Fmoc-Ala, Fmoc-Arg(pbf)-OH, Fmoc-Asn(Trt)-OH, Fmoc-Asp(Otbu)-OH, Fmoc-Gln(Trt)-OH, Fmoc-Glu(Otbu)-OH, Fmoc-Glu-Otbu, Fmoc-Gly-OH, Fmoc-His(Trt)-OH, Fmoc-Ile-OH, Boc-Ile-OH, Fmoc-Leu-OH, Fmoc-Val-OH, Fmoc-Lys(boc)-OH, Fmoc-Ser(Otbu)-OH, Fmoc-Thr(Otbu)-OH, Fmoc-Tyr(Otbu)-OH, FmocTrp(Boc)-OH, Fmoc-Phe-OH, and they were purchased from either Protein Technologies, Novabiochem Merck or IRIS Biotech (Germany). Biotin was purchased from Sigma. Fmoc-preloaded resin was used and purchased from Merck Millipore. Fmoc-8-amino-3,6-dioxaoctanoic acid (Fmoc-Ado-OH) was purchased from Flamma Group, Italy.

Gallic acid (GA, ≥98.0%) and 3-(2-aminoethylamino)propyltrimethoxysilane (AMETAM, ≥98.0%) were purchased from Fluka, polyethylenimine (PEI, M_w~2000, 50% wt. solution in water), (3-aminopropyl)trimethoxysilane (APTMS, 97%), (3-chloropropyl)trimethoxysilane (CPTMS, 97+%), folic acid (FA, ≥97%), diisopropylcarbodiimide (DIC, ≥98.0%), N,N-diisopropylethylamine (DIPEA, ≥99.0%) and all solvents used in the study were purchased from Sigma-Aldrich and used without further purification. SBA-15 mesoporous silica (8–11 nm pore diameter, 600 m² g^-1 surface area and 1–2 μm particle size) was purchased from ACS Material.

Four-arm PEG (MW = 20 kDa) (PEG-OH) and four-arm
poly(ethylene glycol)-thiol (MW = 10 kDa) (PEG-SH) were purchased
from JenKem Technology USA (Plano, Texas). Diisopropylcarbodiimide,
4-(dimethylamino)pyridine, 5-norbornene-2-carboxylic acid, and anhydrous
dichloromethane were purchased from Sigma-Aldrich (St. Louis, Missouri).
2,2′-Azobis[2-(2-imidazolin-2-yl) propane]dihydrochloride (VA-044)
was purchased from FUJIFILM Wako Pure Chemical Corporation (Richmond,
Virginia). 5-((2-(and-3)-S-(Acetylmercapto) succinoyl) amino) (SAMSA)
fluorescein was purchased from Fisher Scientific (Eugene, Oregon).
Minimum Essential Medium, penicillin–streptomycin, and GlutaMAX
were purchased from Fisher Scientific (Eugene, Oregon). SMP foams
were graciously provided by Shape Memory Medical, Inc. (Santa Clara,
California).

Lipases from Thermomyces lanuginosus (TLL) (Lipozyme TL100L), Candida antarctica (fraction B) (CAL-B) (Lipozyme CALBL), Lecitase ultra (LECI), and Rhizomucor miehei (RML) (Palatase 20000L) and β-galactosidase Lactozym were kindly donated by Novozymes (Bagsværd, Denmark). Lipase from Pseudomonas fluorescens (PFL) (Sigma-Aldrich, cat. no 534730, St. Louis, MI, USA), Lipase from Candida rugosa (CRL) (Sigma-Aldrich, cat. no. L1754), betagalactosidase from E. coli, geranyl-amine, N-hydroxysuccinimide (NHS), carboxymethylcelullose (CM), 1-O-(4-nitrophenyl)-β-d-galactopyranoside (pNP-Gal), diisopropylcarbodiimide (DIC), trimethylamine, p-nitrophenylbutyrate (pNPB), selenometheonine, 4-azide-l-homoalanine, and l-DOPA were from Sigma-Aldrich (Saint Louis, MO, USA). Tyrosine from A. bisporus was produced as reported [40 (link)]. 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) was acquired from Tokyo Kasei (Tokyo, Japan). SB-IDA405 Sepabeads (SP) resin was from Resindion srl (Binasco, Italy). The scanning electron microscopy (SEM) imaging was performed on a TM-1000 Hitachi (Tokio, Japan) microscope. The X-ray diffraction (XRD) pattern was obtained using a Texture Analysis Diffractometer D8 Advance Bruker (Billerica, MA, USA) with Cu Kα radiation. The spectrophotometric analyses were run on a V-730 spectrophotometer JASCO (Tokio, Japan).