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N n dicyclohexylcarbodiimide dcc n n dimethylaminopyridine dmap trifluoroacetic acid tfa

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N,N-dicyclohexylcarbodiimide (DCC) is a coupling agent used in organic synthesis to activate carboxylic acids for reactions with alcohols, amines, and other nucleophiles. N,N-dimethylaminopyridine (DMAP) is a nucleophilic catalyst that can be used in conjunction with DCC to facilitate these coupling reactions. Trifluoroacetic acid (TFA) is a strong organic acid commonly used in various synthetic procedures, such as deprotection reactions and purification of peptides and other organic compounds.

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2 protocols using n n dicyclohexylcarbodiimide dcc n n dimethylaminopyridine dmap trifluoroacetic acid tfa

1

Gemcitabine Synthesis and Characterization

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Gemcitabine (Gem) was extracted from the lyophilized powder (Gemzar™) supplied by Eli Lilly Pharmaceuticals (Indianapolis, IN, USA). The tert-butyloxycarbonyl (Boc) protected amino acids Boc-l-valine, Boc-l-phenylalanine, Boc-d-valine, Boc-d-phenylalanine, and Boc-l-phenylalanyl-l-tyrosine were obtained from Chem-Impex (Wood Dale, IL, USA). High-performance liquid chromatography (HPLC) grade acetonitrile was obtained from Fisher Scientific (St. Louis, MO, USA). N,N-dicyclohexylcarbodiimide (DCC), N,N-dimethylaminopyridine (DMAP), trifluoroacetic acid (TFA), and all other reagents and solvents were purchased from Aldrich Chemical Co. (Milwaukee, WI, USA). Cell culture reagents were obtained from Invitrogen (Carlsbad, CA, USA) and cell culture supplies were obtained from Corning (Corning, NY, USA) and Falcon (Lincoln Park, NJ, USA). All chemicals were either analytical or HPLC grade.
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2

Synthesis of Gemcitabine-Peptide Conjugates

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Gemcitabine (Gem) was extracted from the lyophilized powder (Gemzar™) supplied by Eli Lilly Pharmaceuticals (Indianapolis, IN, USA). The tert-butyloxycarbonyl (Boc) protected amino acids Boc-l-valine, Boc-l-phenylalanine, Boc-d-valine, Boc-d-phenylalanine, and Boc-l-phenylalanyl-l-tyrosine were obtained from Chem-Impex (Wood Dale, IL, USA). High-performance liquid chromatography (HPLC) grade acetonitrile was obtained from Fisher Scientific (St. Louis, MO, USA). N,N-dicyclohexylcarbodiimide (DCC), N,N-dimethylaminopyridine (DMAP), trifluoroacetic acid (TFA), and all other reagents and solvents were purchased from Aldrich Chemical Co. (Milwaukee, WI, USA). Cell culture reagents were obtained from Invitrogen (Carlsbad, CA, USA) and cell culture supplies were obtained from Corning (Corning, NY, USA) and Falcon (Lincoln Park, NJ, USA). All chemicals were either analytical or HPLC grade.
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