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

作者：Hostetler Matthew A; Lipton Mark A^*

来源：Journal of Organic Chemistry, 2018, 83(15): 7762-7770.

DOI：10.1021/acs.joc.8b00658

A one-step preparation of 1,1-dimethylallyl (DMA) esters was optimized for the C-terminal protection of a range of Fmocprotected 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.

• 出版日期2018-8-3