ChemInform Abstract: High-Yielding Staudinger Ligation of a Phosphinothioester and Azide to Form a Peptide.
Abstract
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ChemInform Abstract
Thioesters such as (IX) and (XIV), prepared from phosphinothiol (VII) and thioesters like (VIII) and (XIII) by transthioesterification (or by DCC coupling with the corresponding acids), undergo Staudinger ligation with azide (X) to give peptides with high yields. In contrast, thioesters derived from thiol (XII) afford the corresponding peptides in significantly lower yields. In addition, the synthesis of the previously unknown thiol (VII) is described.
