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Max-Planck-Institut für Polymerforschung Max Planck Institute for Polymer Research. Lysine-modified valinomycin as a biosensor. Julia Braunagel. Ile de Berder 28.08.2007. Outline. Membrane model systems 2.Tethered bilayer lipid membranes 3.Cornell´s biosensor

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Lysine modified valinomycin as a biosensor

Max-Planck-Institut für Polymerforschung

Max Planck Institute for Polymer Research

Lysine-modified valinomycin as a biosensor

Julia Braunagel

Ile de Berder

28.08.2007


Lysine modified valinomycin as a biosensor

Outline

  • Membrane model systems

  • 2.Tethered bilayer lipid membranes

  • 3.Cornell´s biosensor

  • 4.Valinomycin as a biosensor


Lysine modified valinomycin as a biosensor

Model systems

Vesicles

sBLM‘s

BLM‘s

tBLM‘s

Picture: F. Giess


Lysine modified valinomycin as a biosensor

Ion Channel

Lipid Bi-Layer

Tether (Spacerunit)

Substrate

Tethered bilayer lipid membranes, tBLMs

  • Key features of a suitable system:

    • Insulating

    • Robust

    • Stable

    • Fluid

    • Homogeneous

Cornell et al., Nature, 387 (1997) p. 580

Terrettaz et al., Angew. Chem. 40 (2001) p.1740

Schiller et al.,Angew. Chem.,42(2003) p.208

Naumann et al, Langmuir, 19(2003) p. 5435

Atanasov et al., Biophy. J. 89 (2005) p. 1780

Köper et al, Advances in Planar Lipid Bilayers (2006)


Lysine modified valinomycin as a biosensor

Preparation of a tBLM


Lysine modified valinomycin as a biosensor

Spacer

Phyt

Anchor

n

DPG

A generic tBLM system

Lipid

n = 4, 6, 8, 12, 14

X = Lipoic Acid, SH: Au, Ag, Cu,Fe, Ni, Pt, GaAs,Hg

X = SiY: silicon oxide;

(Y = Cl, OCH3, OC2H5)

V. Atanasov, et al.

Bioconjugated Chemistry 17, 631-637 (2006)


Lysine modified valinomycin as a biosensor

DPTL, 2,3-di-O-phytanyl-sn-glycerol-1-tetraethylene glycol-D,L-α-lipoic acid ester

Properties:

-R >10MW cm2

-C < 1µF cm-2

-Semi-Fluid

-Robust

-Stable

-Reproducible

Schiller et al., Angew. Chem., 42(2003) p.208

Patent : DE 102 22 588.5; EP 03 011 554.7; US-2004-0023304-A1

Available at diverchim.com


Lysine modified valinomycin as a biosensor

Incorporation of Gramicidin ion-channel

Cations e.g. K+

tBLM with Gramicidin

Gold


Lysine modified valinomycin as a biosensor

Cornell´s biosensor

Streptavidin

Biotin

Tethered membrane-spanning lipids

B.A. Cornell et al., 1997, Nature 387: 580-583


Lysine modified valinomycin as a biosensor

Valinomycin based biosensor


Lysine modified valinomycin as a biosensor

Valinomycin based biosensor

  • Advantages:

  • easy synthesis on a multi-milligram scale

  • very specific to potassium

  • no tethered membrane-spanning lipids necessary

  • no anchorage on the surface necessary


Lysine modified valinomycin as a biosensor

Valinomycin based biosensor


Lysine modified valinomycin as a biosensor

Valinomycin

Ester carbonyls are turned inwards, forming 6 ion-dipole bonds with a centrally situated cation.

Modification on the backbone of the dodecadepsipeptide leads to the lost of complexing properties.

Exchange in the amino acid sequence

Shemyakin et al., 1974, FEBS Letters44: 1-21


Lysine modified valinomycin as a biosensor

Lysine-modified Valinomycin

Exchange of one L-Valin by an L-Lysine

possibility to bind e.g. biotin to valinomycin

The synthesis is described on my poster.


Lysine modified valinomycin as a biosensor

Acknowledgment

Prof. W. Knoll

Dr. I. Köper

Dr. V. Atanasov

Thank you for your attention!


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