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Synfacts 2014; 10(9): 0989
DOI: 10.1055/s-0034-1378995
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

An Immobilized Cobalt Complex for Alkyne-Tagged Peptide Enrichment

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Takuma Sato
Miyazaki A, Asanuma M, Dodo K, Egami H, Sodeoka M * ERATO, Japan Science and Technology Agency, Wako and RIKEN Center for Sustainable Resource Science, Wako, Japan
A ‘Catch-and-Release’ Protocol for Alkyne-Tagged Molecules Based on a Resin-Bound Cobalt Complex for Peptide Enrichment in Aqueous Media.

Chem. Eur. J. 2014;
20: 8116-8128
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Publication History

Publication Date:
18 August 2014 (online)

 
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Key words

alkynes - peptides - Nicholas reaction - solid-phase synthesis - cobalt

Significance

A ‘catch-and-release’ protocol for the enrichment of alkyne-tagged biomolecules using a resin-supported phosphine cobalt carbonyl complex in aqueous media was developed. The reaction of a PS-PEG resin (TentaGel) supported cobalt complex 7 with a propargyloxycarbonyl-functionalized peptide 6 (prepared from a dipeptide 1 over four steps) proceeded in 30% EtOH/HEPES buffer solution to give the corresponding dicobalt alkyne complex 8. The following Nicholas-type reaction–decarboxylation sequence of 8 afforded the free amine 4 in 77% yield.


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Comment

The reaction of the alkyne-tagged dipeptide 6 with the solid-supported cobalt complex 7 was performed under high-dilution conditions (50 μM of 6). After the complexation of 6 with 7, the resulting polymeric peptide complex was treated with 5% TFA to release the free amine 4 as a single product, where an alkyne 6 was not detected in the solution by mass spectrometry.


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