Letters in Peptide Science

, Volume 6, Issue 2–3, pp 135–142 | Cite as

Heterobifunctionalized tetraethylene glycol: A spacer for surface attachment of viral peptide epitopes for ELISA and derivatization of membrane modifying peptides

  • Jürgen Mack
  • Stefan Kienle
  • Dietmar Leipert
  • Thomas Redemann
  • Wolfgang Kraas
  • Günther Jung
Article

Summary

New hydrophilic linkers of the formula Fmoc-NHCH2CH2COO(CH2CH2O)4X (X=COCH2CH2COOH Fmoc-Ats (2), X=CONHCH2COOH Fmoc-Atg (4) and X=CONHCH2CH2COOH Fmoc-Ata (5) have been prepared by heterobifunctional modification of tetraethylene glycol as starting material. These linkers represent a useful tool for solid phase peptide synthesis according to Fmoc/tBu strategy. Two examples are presented to illustrate the applicability of these building blocks: (i) spacing between biotin and a peptide epitope of the hepatitis C virus and evaluation in a biotin-streptavidin ELISA, and (ii) coupling of the new linker to the N- and C-terminus of the peptide antibiotic alamethicin to show eventual influences on the peptide's α-helical conformation.

Key words

alamethicin circular dichroism ELISA hepatitis C spacer tetraethylene glycol 

Abbreviations

ABTS

2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid)

BSA

bovine serum albumine

Dde

1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl

DMAP

N,N-dimethylaminopyridine

EDT

ethanedithiol

NMP

N-methylpyrrolidone

PBS

phosphate buffered saline

EEG

polyethylene glycol

RP

reversed phase

SPPS

solid phase peptide synthesis

TBTU

O-(1-H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

TEG

tetraethylene glycol

TFFH

tetramethylfluoroformamidinium-hexafluorophosphate

TIS

triisopropylsilane

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Copyright information

© Kluwer Academic Publishers 1999

Authors and Affiliations

  • Jürgen Mack
    • 1
  • Stefan Kienle
    • 1
  • Dietmar Leipert
    • 1
  • Thomas Redemann
    • 1
  • Wolfgang Kraas
    • 1
  • Günther Jung
    • 1
  1. 1.Department of Organic ChemistryUniversity of TübingenTübingenGermany

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