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Synthesis of single- and multiple-stranded cystine-rich peptides.

Abstract：

:The large abundance of bioactive single- and multiple-stranded cystine-rich peptides in nature has fostered the development of orthogonal thiol-protection schemes and of efficient chemistries for regioselective disulfide formation in synthetic replica for decades. In parallel to these entirely synthetic strategies, an increased knowledge of oxidative refolding mechanisms of proteins has been accumulated, and the collective experience with air oxidation of cysteine-rich peptides into their native disulfide frameworks have largely confirmed Anfinsen's principle of the self-assembly of polypeptide chains. In fact, a continuously growing number of cysteine-rich bioactive peptides from the most diverse sources and with differing cysteine patterns were found to retain the critical sequence-encoded structural information for correct oxidative folding into the native structures as dominant isomers, although in the biosynthetic pathways the mature peptide forms are mostly generated by posttranslational processing of folded precursors. Such self-assembly processes can be optimized by opportune manipulation of the experimental conditions or by induction of productive intermediates. But there are also numerous cases where folding and disulfide formation are thermodynamically not coupled and where the application of a defined succession of regioselective cysteine pairings still represents the method of choice to install the desired native or non-native cystine frameworks. Among our contributions to the state of the art in the synthesis of cystine-rich peptides, we have mainly addressed the induction of correct oxidative refolding of single-stranded cysteine-rich peptides into their native structures by the use of selenocysteine and suitable strategies for disulfide-mediated assembly of monomers into defined oligomers as mimics of homo- and heterotrimeric collagens as a synthetic approach for the development of new biomaterials.

journal_name

Biopolymers

journal_title

Biopolymers

authors

Moroder L,Musiol HJ,Götz M,Renner C

doi

10.1002/bip.20174

subject

Has Abstract

pub_date

2005-01-01 00:00:00

pages

85-97

issue

2-3

eissn

0006-3525

issn

1097-0282

journal_volume

pub_type

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Synthesis of single- and multiple-stranded cystine-rich peptides.