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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Electrophilic S‐Trifluoromethylation of Cysteine Side Chains in α‐ and β‐Peptides: Isolation of Trifluoro‐methylated Sandostatin® (Octreotide) Derivatives
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The new electrophilic trifluoromethylating 1-(trifluorsic acid)-benziodoxole reagents A and B have been used to selectively attach CF3 groups to the S-atom of cysteine side chains of α- and β-peptides and may be replaced by H (Na/NH3), an overall Cys/Ala conversion.
Preparation of enantiomerically enriched (S)-ethyl 3-hydroxy 4,4,4-trifluorobutanoate using whole cells of Candida parapsilosis ATCC 7330
Joy and flustration with organofluorine compounds - a fluorous autobiography.
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Some cases of totally unexpected effects on reactivity and structure exerted by fluoro-substitution are presented and taken as examples for the use of the terms flustrate and flustration in connection with organo-fluorine chemistry.
Biogenesis of Ion Channels
TLDR
Two simple polymers inorganic polyphosphate (PolyP) and poly-(R)-3-hydroxybutyrate (PHB) were available in the primordial environment that could join together to provide the energy for evolving cells.
Bioreduction with Efficient Recycling of NADPH by Coupled Permeabilized Microorganisms
TLDR
The method results in practical synthesis of (R)-ethyl 3-hydroxy-4, 4,4,4-trifluorobutyrate, and the principle described here is generally applicable to other microbial reductions with cofactor recycling.
Introduction Biogenesis of Ion
TLDR
Two simple polymers inorganic polyphosphate (PolyP) and poly-(R)-3-hydroxybutyrate (PHB) were available in the primordial environment that could join together to provide the energy for evolving cells.

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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.
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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)…
Synthesis of Linear Oligomers of (R)-3-Hydroxybutyrate and Solid-State Structural Investigations by Electron Microscopy and X-ray Scattering
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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