Synthesis and application of a Sec 2-containing oligopeptide for method evaluation purposes in selenium speciation

M. Dernovics, Andrea Vass, Anikó Németh, Anna Magyar

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Sec 2-containing oligopeptide was synthesized directly from Sec 2 with the traditional liquid phase peptide synthesis without addressing the usually applied and complex solid phase (SPPS) protocol driving through a protected Sec residue and site-oriented oxidation into a diselenide bridge. Effective solubilization of Sec 2 in dimethylformamide and its pH-controlled access to pentachlorophenol-activated peptides to couple with were of crucial importance to achieve good yield (>50%) of synthesis, monitored by HPLC-UV, SEC-ICP-MS and HPLC-ESI-MS techniques. To demonstrate the possible application of the new compound, (Boc-GGFG)-Sec 2-(Boc-GGFG) (m/z 1173.3, [MH]), it was utilized to compare the effect of the two most addressed sample preparation techniques, i.e., methanesulphonic acid (MSA) based digestion and proteolytic digestion with protease XIV, on the Sec residue. The study revealed that the use of MSA resulted in the decomposition of Sec even after derivatization with iodoacetamide.

Original languageEnglish
Pages (from-to)186-193
Number of pages8
JournalTalanta
Volume99
DOIs
Publication statusPublished - Sep 15 2012

Fingerprint

Oligopeptides
Selenium
Digestion
High Pressure Liquid Chromatography
Pentachlorophenol
Iodoacetamide
Dimethylformamide
Pronase
Peptides
Decomposition
Oxidation
Liquids
methanesulfonic acid
stable plasma protein solution

Keywords

  • Oligopeptide
  • Selenium
  • Selenocysteine
  • Selenocystine
  • Speciation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis and application of a Sec 2-containing oligopeptide for method evaluation purposes in selenium speciation. / Dernovics, M.; Vass, Andrea; Németh, Anikó; Magyar, Anna.

In: Talanta, Vol. 99, 15.09.2012, p. 186-193.

Research output: Contribution to journalArticle

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