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4 dimethylaminopyridine

Manufactured by Thermo Fisher Scientific
Sourced in United States, United Kingdom

4-dimethylaminopyridine is a chemical compound commonly used as a catalyst or reagent in organic synthesis. It functions as a nucleophilic acyl transfer agent, facilitating various chemical reactions. The compound's core function is to promote and enhance the efficiency of certain organic transformations, without making claims about its specific intended uses.

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21 protocols using 4 dimethylaminopyridine

1

Synthesis and Characterization of Fmoc-Ala-13C3

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All solvents and chemicals were reagent grade. L-Alanine, thionyl chloride and Fmoc-Ala-OH-13C3 were purchased from Sigma–Aldrich; 4-dimethylaminopyridine and HOBt were purchased from Acros Organics; DCC, methyl iodide, and piperidine were purchased from Alfa Aesar. 2-(Diphenylphosphino)benzoic acid 3 was prepared according to a literature protocol.30 (link)
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2

Synthesis and Characterization of Glyco-Nanoparticles

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All chemicals were used as supplied unless otherwise stated. Acetone, dichloromethane, toluene, methanol, diethyl ether were purchased from Fischer Scientific at laboratory grade. Dodecane thiol (≥98%), potassium phosphate tribasic (≥98%), carbon disulfide (99%), N-hydroxethyl acrylamide (97%), 4,4′-azobis(4-cyanovaleric acid) (98%), mesitylene (reagent grade), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (≥98%) were all purchased from Sigma-Aldrich. 2-Bromo-2-methylpropionic acid (98%), 4-(dimethylamino)pyridine (99%), pentafluorophenol (99%), triethylamine (99%) were purchased from Acros. Microtitre plates were purchased from Greiner Bio-one. 10 mmol HEPES buffer containing 0.05 M NaCl, 0.1 mM CaCl2 and 0.01 mM MnCl2 (pH 7.5, HEPES) was prepared in 200 mL of milliQ water (with a resistance > 19 mOhms). 60 nm gold nanoparticles were obtained from BBI solutions. Concanavalin A and soybean agglutinin and Ricinus communis agglutinin-120 were purchased from Vector Labs.
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3

Synthesis of Dendrimer-Drug Conjugates

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EDA core PAMAM dendrimer G4.5 caboxylate sodium salt was purchased from Dendritech (Midland, MI). 2,2’-Bipyridine, 4-dimethylaminopyridine (DMAP), copper(II) sulfate (CuSO4), (+)-sodium L-ascorbate, 4-(4,6-dimethoxy-(1,3,5)triazin-2-yl)-4-methyl-morpholinium chloride (DMTMM), deuterated solvents, dichloromethane (DCM), dimethyl sulfoxide (DMSO), and other organic solvents were purchased from Acros (Morris Plains, NJ). (S)-(+)-Camptothecin (CPT), propargylamine (PPA), copper bromide (CuBr), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), trifluoroacetic acid (TFA) and silica gel 60 (40-63 μm, 230-400 mesh) were purchased from Sigma-Aldrich (St. Louis, MO). 1-Azido-3,6,9,12,15-pentaoxaoctadecan-18-oic acid (APO) and methoxypoly(ethylene glycol) amine (mPEG-NH2, 2000 g/mol) were purchased from Biomatrik (Jiaxing, Zhejiang, China) and JenKem Technology USA (Plano, TX), respectively. SnakeSkin dialysis tubing 3.5 kDa and 7 kDa MWCO, acetonitrile (ACN), HPLC grade water, phosphate-buffered saline (PBS), and magnesium sulfate (MgSO4) were purchased from Thermo Fisher Scientific (Pittsburg, PA).
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4

Synthesis and Characterization of Glyco-Nanoparticles

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All chemicals were used as supplied unless otherwise stated. Acetone, dichloromethane, toluene, methanol, diethyl ether were purchased from Fischer Scientific at laboratory grade. Dodecane thiol (≥98%), potassium phosphate tribasic (≥98%), carbon disulfide (99%), N-hydroxethyl acrylamide (97%), 4,4′-azobis(4-cyanovaleric acid) (98%), mesitylene (reagent grade), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (≥98%) were all purchased from Sigma-Aldrich. 2-Bromo-2-methylpropionic acid (98%), 4-(dimethylamino)pyridine (99%), pentafluorophenol (99%), triethylamine (99%) were purchased from Acros. Microtitre plates were purchased from Greiner Bio-one. 10 mmol HEPES buffer containing 0.05 M NaCl, 0.1 mM CaCl2 and 0.01 mM MnCl2 (pH 7.5, HEPES) was prepared in 200 mL of milliQ water (with a resistance > 19 mOhms). 60 nm gold nanoparticles were obtained from BBI solutions. Concanavalin A and soybean agglutinin and Ricinus communis agglutinin-120 were purchased from Vector Labs.
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5

Synthesis of Furan-Based Polyesters

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1,3-Cyclopentanediol (15/85 cis/trans), 1,4-cyclohexanedimethanol (38/62 cis/trans), adipoyl chloride, sebacoyl chloride, terephthaloyl chloride, tin(ii) 2-ethyl-hexanoate, and anhydrous chloroform, DMF, THF, and toluene were obtained from Sigma Aldrich. Magnesium(iv) sulfate, 4-dimethylaminopyridine and pyridine were obtained from ACROS. 2,5-Furan-dicarboxylic acid was obtained from ABCR. 1,4-Cyclohexanediol (46/54 cis/trans) was obtained from Alfa Aesar. Ethylene glycol was obtained from TCI. Standard laboratory solvents were obtained from Biosolve. Deuterated solvents were obtained from Buchem BV (Netherlands). The purchased compounds were used directly without further purification, unless otherwise specified.
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6

Synthesis and Characterization of Polymeric Materials

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Betulin
(98%) was purchased from BOC Sciences.
1,18-octadecanedioic acid (C18, >98%), 1,12-dodecanedioic acid
(C12,
>99%), dimethyl itaconate (DMI, >98%), diphenyl(2,4,6-trimethylbenzoyl)phosphine
oxide (TPO, >98%), menthol (>98%), and dibutyltin dilaurate
(>95.0%,
stored at 5 °C) were purchased from TCI America. Itaconic acid
(IA, >99%), chloroform-d3 (CDCl3, >99.8%), dibutyltin oxide (DBTO, 98%), 4-dimethylaminopyridine
(4-DMAP, 99%), and hydroquinone (99%) were purchased from Acros Organics.
Glycerol (≥99.5%) was purchased from Sigma-Aldrich. Methanol
(≥99.8%), dichloromethane (DCM, ≥99.5%), ethyl acetate
(≥99.5%), sodium hydroxide (≥98%), sodium chloride (≥99.0%),
and tetrahydrofuran (THF, HPLC grade) were purchased from VWR. Methacrylic
anhydride (94%, stabilized with ca. 0.2% 2,4-dimethyl-6-tert-butylphenol) was purchased from Alfa Aesar. Magnesium sulfate was
purchased from Thermo Scientific. All chemicals mentioned above were
used as received and stored at room temperature unless otherwise noted.
A Miller-Stephenson PTFE release agent (MS-122) was acquired from
Grainger. Nitrogen (N2, 99.999%), argon (Ar, 99.998%),
and liquid nitrogen (LN2, 99.998%) were purchased from
Airgas and used as received.
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7

Peptide-Polymer Conjugates Synthesis

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N,N-Dimethylacrylamide (DMA, 99%), 4,4′-azobis(4-cyanovaleric acid) (ACVA, ≥98%), benzyl 1H-pyrrole-1-carbodithioate (BPC, 97%), Fmoc-Gly-Wang resin (100–200 mesh, capacity: 0.56 mmol g−1), Fmoc amino acids, triisopropylsilane (98%), propylamine (≥99%), phenyldimethylphosphine (99%), DMF (peptide synthesis grade quality), magnesium chloride hexahydrate (99%), and pentafluorophenol (≥99%) were purchased from Sigma-Aldrich. 1-[bis(Dimethylamino)methylene]-1H-benzotriazolium hexafluorophosphate 3-oxide (HBTU, 98%), N,N-diisopropylethylamine (DIPEA, 99%), and N,N-dicyclohexylcarbodiimide (DCC, 99%) were purchased from Alfa Aesar. 4-Dimethylaminopyridine (99%), 1,4-dioxane (extra dry, 99.8%), and trifluoroacetic acid (TFA, 99.5%) were purchased from Acros Organics. All other solvents were analytical grade and purchased from Fisher Scientific. DMA was vacuum distilled, and ACVA was recrystallized twice from methanol prior to use. All other chemicals were used as received, without any purification. 4-Vinylbenzyl N-pyrrole carbodithioate (VBPC) was synthesized and purified in-house as previously reported by Rimmer et al. [42 (link)].
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8

Synthesis of Hybrid Biomaterials

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Laminarin
(LAM) from Eisenia bicyclis (CAS: 9008–22–4)
and lithium phenyl(2,4,6-trimethylbenzoyl)phosphinate
(LAP) were purchased from Biosynth. Tetraethyl orthosilicate (TEOS,
98%), hexadecyltrimethylammonium bromide (CTAB, 98%), calcium
chloride anhydrous, dry dimethyl sulfoxide (DMSO, p.a. ≤ 0.02%
water), and formaldehyde were acquired from Sigma-Aldrich. 3-(Trimethoxysilyl)propyl
acrylate (stabilized with BHT) (TMOS-PA, 93%) and glycidyl methacrylate
(stabilized with MEHQ, 95%) were purchased from TCI Chemicals. Disodium
hydrogen phosphate monohydrate and alginic acid sodium salt (Mw 10,000–600 000 Da, Alginate)
were bought from PanReac AppliChem. 4-Dimethylaminopyridine (DMAP,
99%) and toluene (extra dry, 99.85%) were obtained from ACROS Organics.
Unless otherwise specified, all chemicals were used as received without
further purification.
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9

Synthesis and Purification of PCL-b-PEG

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The following analytical-grade chemicals were purchased and used without further purification: 2,3,5-triiodobenzoic acid (Changzhou Ilhang Fine Chemical Co. Ltd, China), thionyl chloride (Acros Organics, 99.5%), sodium carbonate, dichloromethane (Acros Organics, 99.9%). N-methyl-2pyrrolidone (NMP, 99.5%), pyridine (99.5%) and 4dimethylaminopyridine (DMAP, 99.5%) were purchased from Acros Organics in anhydrous grade over molecular sieves in an AcroSeal packaging. Poly(vinyl alcohol) (PVAL, Sigma-Aldrich, 98% hydrolyzed, average molar mass MW = 13,000-23,000 Da) was dried at 40 °C in an oven for 24 h under vacuum before use. Tetrahydrofuran (THF, Fisher Scientific), absolute anhydrous ethanol (Carlo Erba) were used in purification processes. The polycaprolactone-block-poly(ethylene glycol) (PCL-b-PEG block copolymer) was synthesized by polymerization of caprolactone initiated by poly(ethylene glycol) monomethyl ether catalyzed by tin octanoate as reported in refs 58, 59 The degrees of polymerization of the poly(caprolactone) and. poly(ethylene glycol) blocks were 65 and 113 respectively (PCL65-b-PEG113). Deionized water of 18 Ω•cm resistivity was used for all preparations.
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10

Synthesis of FMOC-protected Peptides

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N-Fluorenyl-9-methoxycarbonyl (FMOC)-protected L-amino acids (Fmoc-Gly-OH, Fmoc-Lys(Boc)-OH) and 2-chlorotrityl chloride resin (loading: 1.20 mmol/g) were purchased from GL Biochem Ltd. (Shanghai, People’s Republic of China). N,N-Diisopropyl ethylamine (DIEA), ninhydrin, N,N,N,N-tetramethyl-O-(1H-benzontriazol-1-yl) uranium hexafluorphosphate (HBTU), 1-Hydroxybenzontriazole (HOBt), trifluoroacetic acid (TFA), triisopropylsilane (Tis), dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP), and N-hydroxysuccinimide (NHS) were purchased from Alfa Aesar (Ward Hill, MA, USA). Succinic anhydride (SA), ethanolamine (EA), N,N-dimethylformamide (DMF), N,N-dimethyacetamide (DMAc), piperidine and triethylamine (TEA) were purchase from Sigma-Aldrich (Burlington, MA, USA).
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