Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis | Zendy

Tobias M. Postma | Zendy; Fernando Alberício | Zendy

Open Access

Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis

Author(s) -

Tobias M. Postma,

Fernando Alberício

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol5004725

Subject(s) - chemistry , peptide , cysteine , thiol , combinatorial chemistry , peptide synthesis , solid phase synthesis , phase (matter) , stereochemistry , organic chemistry , biochemistry , enzyme

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.

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