Preparation of the β2-homoselenocysteine derivatives Fmoc-(S)-β2hSec(PMB)-OH and Boc-(S)-β2hSec(PMB)- OH for solution and solid-phase peptide synthesis

Article abstract of DOI:10.1002/hlca.201000409

Fmoc-β²hSer(^tBu)-OH was converted to Fmoc-β²hSec(PMB)-OH in five steps. To avoid elimination of HSeR, the selenyl group was introduced in the second last step (Fmoc- β²hSer(Ts)-OAll→Fmoc-β²hSec(PMB)-OAll). In a similar way, the N-Boc-protected compound was prepared. With the β²hSe-derivatives, 21 β²-amino-acid building blocks with proteinogenic side chains are now available for peptide synthesis. Copyright