A new water soluble 3,6,9-trioxaundecanedioic acid-based linker and biotinylating reagent

Ádám Bartos, F. Hudecz, K. Uray

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Biotinylated peptides often have low solubility in water. In this Letter, we describe a new method to synthesize a biotinylating reagent for water-solubilizing hydrophobic peptides. The biotinyl-6-aminohexanoic derivatives prepared contain a hydrophilic 3,6,9-trioxaundecanedioic acid linker moiety between the biotin and the peptide to improve the water solubility, and also to function as a spacer. The monoesterified derivative of 3,6,9-trioxaundecanedioic acid was synthesized, and the Fmoc-protected ethylenediamine was used to link to the carboxylic group of biotin. The hydrophilic nature of this new biotin-peptide conjugate was also demonstrated in a comparative analysis of compounds containing a biotinyl-6-aminohexanoic acid or 3,6,9-trioxaundecanedioic acid derivative.

Original languageEnglish
Pages (from-to)2661-2663
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number22
DOIs
Publication statusPublished - Jun 3 2009

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Biotin
Peptides
ethylenediamine
Acids
Water
Derivatives
Solubility
Aminocaproic Acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A new water soluble 3,6,9-trioxaundecanedioic acid-based linker and biotinylating reagent. / Bartos, Ádám; Hudecz, F.; Uray, K.

In: Tetrahedron Letters, Vol. 50, No. 22, 03.06.2009, p. 2661-2663.

Research output: Contribution to journalArticle

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