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  • Building functionalized peptidomimetics: new electroauxiliaries and the use of a chemical oxidant for introducing N-acyliminium ions into peptides.

Building functionalized peptidomimetics: new electroauxiliaries and the use of a chemical oxidant for introducing N-acyliminium ions into peptides.

Organic letters (2003-08-29)
Haizhou Sun, Kevin D Moeller
RESUMEN

[reaction: see text] The removal of electroauxiliaries from peptide substrates with chemical oxidants has been examined as a method for inserting N-acyliminium ions into the peptides. To this end, it was found that both 4-methoxyphenyldimethylsilyl and 2,4-dimethoxyphenyldimethylsilyl electroauxiliaries were readily cleaved with the use of ceric ammonium nitrate. Of the two groups, the 2,4-dimethoxyphenyldimethylsilyl electroauxiliary was the most labile under the oxidative conditions. The oxidation reactions were shown to be compatible with the use of a solid-phase substrate.

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Sigma-Aldrich
Ammonium cerium(IV) nitrate, ACS reagent, ≥98.5%
Sigma-Aldrich
Ammonium cerium(IV) nitrate, puriss. p.a., ACS reagent, ≥98.5% (RT)
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ≥99.99% trace metals basis
Sigma-Aldrich
Ammonium cerium(IV) nitrate, ≥98% (titration)
Sigma-Aldrich
Ammonium cerium(IV) nitrate, JIS special grade, ≥95.0%