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2 protocols using fmoc l proline

1

Synthesis of SN-38-PEG-DBCO Conjugate

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All reagents listed below were obtained from
commercial sources and used without further purification. H-His (Trt)-2-Cl-Trt
resin and H-Val-2-Cl-Trt resin were purchased from AAPPTEC (Louisville,
KY). Boc-L-alanine, Fmoc-L-alanine, Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydro-benzofuran-5-sulfonyl)-l-arginine, Nim-Trityl-L-histidine tert-butyl ester
hydrochloride, Fmoc-L-isoleucine, Fmoc-O-tert-butyl-L-tyrosine, Fmoc-L-proline,
Fmoc-6-aminohexanoic acid, 4-aminobenzyl alcohol (PABA), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium
hexafluorophosphate (HATU),N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline(EEDQ),N,N′-diisopropylethylamine
(DIPEA), trifluoroacetic acid (TFA), and piperidine were purchased
from Chem Impex (Wood Dale, IL). 7-Ethyl-10-hydroxycamptothecin (SN-38)
was purchased from Biosynth (San Diego, CA). N,N-dimethylformamide
(DMF), dichloromethane (DCM), methanol (MeOH), tetrahydrofuran (THF),
acetonitrile (ACN), ethyl acetate (EtOAc), hexane, triisopropylsilane
(TIPS), phosphorus tribromide, diethyl ether (Et2O), silica
gel, 18-crown-6, and potassium carbonate were purchased from Sigma-Aldrich
(Burlington, MA). N3-PEG4-acid, Fmoc-N-amido-PEG3-acid, and DBCO-C6-acid were purchased from BroadPharm
(San Diego, CA).
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2

Healthy Human Serum Compound Analysis

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Healthy human blood serum (S7023-50 mL) was purchased from Sigma-Aldrich (St. Louis, MO). FMOC-L-proline was procured from Chem-Impex International (Wood Dale, IL). Leucine enkephalin was obtained from ERA (Golden, CO). Arginyl-glycyl-aspartic acid, L-fucose, L-rhamnose, 1,5-anhydrosorbitol, D-fucose, L-rhamnulose, 2-deoxy-D-glucose, and 2deoxy-D-galactose were acquired from Sigma-Aldrich Bilirubin, and suberic acid was obtained from Alfa Aesar (Ward Hill, MA). Ricinoleic acid was purchased from MP Biomedicals (Santa Ana, CA). Docosahexaenoic acid and 3-oxo stearic acid were acquired from Cayman Chemical Company (Ann Arbor, MI). LysoPE(16:0) was obtained from Avanti Polar Lipids (Alabaster, AL). LC-MS grade methanol was purchased from J.T. Baker Avantor Performance Materials (Center Valley, PA). Ultrapure water with 18.2 MΩ cm resistivity (Barnstead Nanopure, Thermo Fisher Scientific, Waltham, MA) was used to prepare chromatographic mobile phases.
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