A rapid and efficient method for the synthesis of selectively S-Trt or S-Mmt protected Cys-containing peptides.

Abstract:

:Selective removal of protecting groups under different cleavage mechanisms could be an asset in peptide synthesis, since it provides the feasibility to incorporate different functional groups in similar reactive centres. However, selective protection/deprotection of orthogonal protecting groups in peptides is still challenging, especially for Cys-containing peptides, where protection of the cysteine side-chain is mandatory since the nucleophilic thiol can be otherwise alkylated, acylated or oxidized. Herein, we established a protocol for the synthesis of Cys-selective S-Trt or S-Mmt protected Cys-containing peptides, in a rapid way. This was achieved by, simply fine-tuning the carbocation scavenger in the final acidolytic release of the peptide from the solid support in the classic SPPS.

journal_name

Amino Acids

journal_title

Amino acids

authors

Stathopoulos P,Papas S,Sakka M,Tzakos AG,Tsikaris V

doi

10.1007/s00726-014-1696-0

subject

Has Abstract

pub_date

2014-05-01 00:00:00

pages

1367-76

issue

5

eissn

0939-4451

issn

1438-2199

journal_volume

46

pub_type

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