A comprehensive one-pot synthesis of protected cysteine and selenocysteine SPPS derivatives.

Abstract:

:A proof-of-principle methodology is presented in which all commercially-available cysteine (Cys) and selenocysteine (Sec) solid phase peptide synthesis (SPPS) derivatives are synthesized in high yield from easily prepared protected dichalcogenide precursors. A Zn-mediated biphasic reduction process applied to a series of four bis-N(α)-protected dichalcogenide compounds allows facile conversion to their corresponding thiol and selenol intermediates followed by insitu S- or Se-alkylation with various electrophiles to directly access twenty one known Cys and Sec SPPS derivatives. Most of these derivatives were able to be precipitated in crude form out of petroleum ether in sufficient purity for direct use as peptide building blocks. Subsequent incorporation of these derivatives into peptide models nicely illustrates their viability and applicability toward SPPS.

journal_name

Protein Pept Lett

authors

Flemer S

subject

Has Abstract

pub_date

2014-01-01 00:00:00

pages

1257-64

issue

12

eissn

0929-8665

issn

1875-5305

pii

PPL-EPUB-60658

journal_volume

21

pub_type

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