Serine-, threonine-, and cysteine-derived cyclic building blocks
(pseudo-prolines, ΨPro) serve as reversible
protecting groups for Ser, Thr, and Cys and prove to be versatile tools
for overcoming some intrinsic problems in
the field of peptide chemistry. The presence of ΨPro within a
peptide sequence results in the disruption of β-sheet
structures considered as a source of intermolecular aggregation during
chain elongation, thus increasing solvation
and coupling kinetics in peptide assembly. Due to their easy
synthetic access and variability in the chemical stability
by modifications introduced in the C-2 position of the
oxazolidine/thiazolidine ring system, this protection
technique
is adaptable to all common strategies in peptide synthesis. We
describe new types of ΨPro building blocks suitable
for standard Fmoc/tBu-based solid phase peptide synthesis,
convergent strategies, and chemoselective ligation
techniques as well as their use as a structure-disrupting, solubilizing
protection technique for the example of peptides
generally considered as “difficult sequences”.
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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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