Beilstein J. Org. Chem.2021,17, 461–484, doi:10.3762/bjoc.17.41
phosphonodepsipeptides with C-1-hydroxyalkylphosphonic acids.
Keywords: alkylation; mimetic; multicomponent condensation; peptide; phosphonopeptide; phosphonodepsipeptide; phosphonylation; Introduction
Both, phosphonopeptides and phosphonodepsipeptides are phosphorus analogues of peptides [1][2][3][4][5]. The
-protected phosphonodepsitetrapeptides 63 were obtained and further transformed to the N-protected phosphonodepsipeptide ester lithium salts 58 after aminolysis with tertiary butylamine and treatment with Dowex-Li+ (Scheme 10) [26].
Synthesis of β-phosphonodepsipeptides
To develop iminocyclitol-based small
and oxidation with sodium periodate, benzyl 2-azido-3-(((benzyloxy)(2-oxoethyl)phosphoryl)oxy)-2-methylpropanoate (69) was obtained. The latter was further transformed to the final phosphonodepsipeptide library 64 after the reductive amination with pyrrolidine derivatives 70 and acylation with a
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Graphical Abstract
Figure 1:
Phosphonopeptides, phosphonodepsipeptides, peptides, and depsipeptides.