16707-70-3Relevant articles and documents
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Wieland,Bartmann
, p. 946,955 (1956)
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In situ carboxyl activation using a silatropic switch: A new approach to amide and peptide constructions
Wu, Wenting,Zhang, Zhihui,Liebeskind, Lanny S.
supporting information; experimental part, p. 14256 - 14259 (2011/11/05)
The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1° and 2° amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.
A novel acid-catalyzed isomerization of Aib-containing thiodipeptides
Lehmann, Juerg,Linden, Anthony,Heimgartner, Heinz
, p. 888 - 908 (2007/10/03)
The use of amino thioacids in the 'azirine/oxazolone method' led to completely epimerized Aib-containing endothiodipeptides (Aib=2- aminoisobutyric acid). It could be established that the epimerization occurred during the acidic hydrolysis of the primaril