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An Optimized Preparation of 1,1-Dimethylallyl Esters and Their Application to Solid-Phase Peptide Synthesis

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journal contribution
posted on 25.06.2018, 00:00 by Matthew A. Hostetler, Mark A. Lipton
A one-step preparation of 1,1-dimethylallyl (DMA) esters was optimized for the C-terminal protection of a range of Fmoc-protected amino acids. This preparation is not sensitive to the scale of reaction and affords the corresponding DMA esters in 70–99% yield with high regioselectivity. Additionally, these DMA-protected amino acids were used with the backbone amide linker (BAL) of Albericio and Barany and found to resist diketopiperazine formation during the synthesis of a series of tripeptide esters. C-terminal DMA protection is compatible with the BAL linkage and allows for standard Fmoc-based methods to be used throughout the synthesis.