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Pseudoproline Dipeptides
Pseudoproline dipeptides contain oxazolidine rings formed from serine or threonine. As pseudoprolines theirselves show rather low-yield couplings, they are utilized as preformed dipeptides which prevent the formation of aggregation-prone secondary structures. Depending on the substitution pattern, cysteine pseudoprolines can be stable towards standard cleavage conditions of tBu/Boc. This fact opens new possibilities for working out a successful strategy for regiospecific disulfide bridge formation in synthesizing multi-cyclic peptides. In addition, pseudoproline-containing peptides typically benefit of enhanced solubilities and coupling efficiencies.
