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| - Convenient Synthesis of N-Methylamino Acids Compatible withFmoc Solid-Phase Peptide Synthesis
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| - Nα-Methylamino acid containing peptides exhibit interesting therapeutic profiles and are increasingly recognized as potentially useful therapeutics. Unfortunately, their synthesis is hampered bythe high price and unavaibility of many Nα-methylamino acids. An efficient and practical preparationof Nα-methyl-Nα-(o-nitrobenzenesulfonyl)-α-amino acids without extensive purification is described.The procedure is based on the well-known N-alkylation of Nα-arylsulfonylamino esters which wasimproved by using dimethyl sulfate and DBU as base. Ester cleavage is efficiently achieved byusing an SN2-type saponification with lithium iodide, avoiding racemization observed with lithiumhydroxide hydrolysis. Compatibility of the synthesized Nα-methylamino acids with Fmoc solid-phase peptide synthesis is demonstrated by using normal coupling conditions to efficiently prepareN-methyl dipeptides. The described procedure allows the preparation of Nα-methylamino acids ina very short period of time and a rapid synthesis of N-methyl peptides using Fmoc solid-phasepeptide synthesis.
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