An Optimized Preparation
of 1,1-Dimethylallyl Esters
and Their Application to Solid-Phase Peptide Synthesis
Version 2 2018-07-18, 19:38
Version 1 2018-07-17, 13:38
Posted on 2018-07-18 - 19:38
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.
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Hostetler, Matthew
A.; Lipton, Mark A. (2018). An Optimized Preparation
of 1,1-Dimethylallyl Esters
and Their Application to Solid-Phase Peptide Synthesis. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.8b00658
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