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Cysteine pseudoprolines for thiol protection and peptide macrocyclization enhancement in Fmoc-based solid-phase peptide synthesis.

ABSTRACT: Contrary to other studies, here we describe cysteine (Cys) pseudoproline-containing peptides with short deprotection times in TFA. The deprotection times fell in the same range as other protecting groups commonly used in SPPS (e.g., 1-3 h). Moreover, when using Cys pseudoprolines as peptide macrocyclization-enhancing moieties a considerable reduction in reaction time was observed compared to a peptide containing trityl protected Cys.

SUBMITTER: Postma TM

PROVIDER: S-EPMC3971734 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Cysteine pseudoprolines for thiol protection and peptide macrocyclization enhancement in Fmoc-based solid-phase peptide synthesis.

Postma Tobias M TM Albericio Fernando F

Organic letters 20140311 6

Contrary to other studies, here we describe cysteine (Cys) pseudoproline-containing peptides with short deprotection times in TFA. The deprotection times fell in the same range as other protecting groups commonly used in SPPS (e.g., 1-3 h). Moreover, when using Cys pseudoprolines as peptide macrocyclization-enhancing moieties a considerable reduction in reaction time was observed compared to a peptide containing trityl protected Cys. ...[more]

PMID: 24617568

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