On the Structure of PHB (=Poly[(R)‐3‐hydroxybutanoic Acid]) in Phospholipid Bilayers: Preparation of Trifluoromethyl‐Labeled Oligo[(R)‐3‐hydroxybutanoic Acid] Derivatives

@article{Rueping2004OnTS,
  title={On the Structure of PHB (=Poly[(R)‐3‐hydroxybutanoic Acid]) in Phospholipid Bilayers: Preparation of Trifluoromethyl‐Labeled Oligo[(R)‐3‐hydroxybutanoic Acid] Derivatives},
  author={Magnus Rueping and Matthias Albert and Dieter Seebach},
  journal={Helvetica Chimica Acta},
  year={2004},
  volume={87},
  pages={2473-2486}
}
Oligomers of (R)-3-hydroxybutanoate (OHB) have previously been shown to transport cations through lipid bilayers. The ion-transport activity has been attributed to the formation of hydrophobic aggregates or pores, which have been identified by fluorescence-microscopy measurements of membrane-incorporated fluorescence-labeled OHBs. To obtain more information about these aggregates, we describe here the synthesis of the specifically F-labeled HB oligomers II–IV for structural investigation by… 
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TLDR
Oligomers of (R)-3-hydroxybutanoic acid consisting of 8, 16, and 32 HB units have been investigated by CD spectroscopy in solution and in a racemic phospholipid bilayer and the distance between the fluorescent groups was calculated, thus providing information about the conformation of the OHB chain.
Oligoesters of (R)-3-Hydroxybutanoic Acid: Transmembrane Transport of Ca2+ across Vesicle Bilayers
TLDR
Oligomers of (R)-3-hydroxybutanoate (OHB) have previously been shown to generate nonselective single-channel conductance through planar phospholipid bilayers in patch-clamp experiments (voltage induced), and the effect of OHBs on the Ca2+ ion permeability through vesicle bilayers is studied.
On the Solution Structure of PHB: Preparation and NMR Analysis of Isotopically Labeled Oligo[(R)‐3‐hydroxybutanoic Acids] (OHBs)
While the chain conformation of poly- and oligo[(R)-3-hydroxybutanoate] (PHB, OHB) is known to be 21- and 31-helical in stretched fibers and in the crystalline state, respectively (Fig. 2), the
Channel‐Forming Activity of 3‐Hydroxybutanoic‐Acid Oligomers in Planar Lipid Bilayers
TLDR
Channel-forming activity of a pure polyester has been demonstrated for the first time and a simple model for the channel-causing structure is proposed, based on the proven tendency of oligo- and poly(3-HB) to form ca.
Cyclische Oligomere von (R)-3-Hydroxybuttersäure: Herstellung und strukturelle Aspekte†
Cyclic Oligomers of (R)-3-Hydroxybutanoic Acid: Preparation and Structural Aspects The oligolides containing three to ten (R)-3-hydroxybutanoate (3-HB) units (12-through 40-membered rings 1–8)
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Repetitive treatment of the biopolymer P(3-HB) (molecular weight > 105 Dalton, storage or s-P(3-HB)), with lithium hexamethyl disilazanid (LHMDS) at −70° in THF leads to a mixture of oligomers with
Synthesis of Amino‐Acid‐, Carbohydrate‐, Coumarin‐, and Biotin‐Labelled Oligo[(R)‐3‐Hydroxybutanoic Acids] (OHB)
TLDR
The benzyl esters 1 – 3 of oligo[(R)-3-hydroxybutanoic acids] (OHB) containing 2, 16, or 32 HB units were coupled at the hydroxy terminus with arginine, glucose, and 7-(dimethylamino)coumarin-4-acetic acid to give the corresponding `labelled' OHB acids.
Cation Transport across Bulk Liquid Organic Membranes with Oligomers of (R)‐3‐Hydroxybutanoic Acid
TLDR
The ionophore properties of the investigated oligomers and oligolides derived from 3-hydroxybutanoic acid are compatible with the alleged role of oligo(3-hydxybutanoate) (c-PHB; ca. 120-mer) as component of ion channels through cell membranes.
Über die Depolymerisierung von Poly-(R)-3-hydroxy-buttersäureester (PHB)
On the Depolymerization of Poly-(R)-3-hydroxy-butanoate (PHB) From cell-free PHB or from dried cells of Alcaligenes eutrophus H 16, which had been grown in an aqueous fructose solution,
Synthesis and Structure of Linear and Cyclic Oligomers of 3-Hydroxybutanoic Acid with Specific Sequences of (R)- and (S)-Configurations
To study the stereoselectivity of enzymatic cleavage of poly(3-hydroxybutyrates) (PHB) in a well-defined system (purified depolymerase and monodisperse substrate of specific relative configuration),
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