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

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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.

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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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Authors and Affiliations

  1. Department of Organic Chemistry, University of Tübingen, Auf der Morgenstelle 18, D-72076, Tübingen, Germany

    Jürgen Mack, Stefan Kienle, Dietmar Leipert, Thomas Redemann, Wolfgang Kraas & Günther Jung

Authors
  1. Jürgen Mack
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  2. Stefan Kienle
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  3. Dietmar Leipert
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  4. Thomas Redemann
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  5. Wolfgang Kraas
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  6. Günther Jung
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Correspondence to Günther Jung.

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Mack, J., Kienle, S., Leipert, D. et al. Heterobifunctionalized tetraethylene glycol: A spacer for surface attachment of viral peptide epitopes for ELISA and derivatization of membrane modifying peptides. Lett Pept Sci 6, 135–142 (1999). https://doi.org/10.1007/BF02443628

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  • DOI: https://doi.org/10.1007/BF02443628

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