Detection, synthesis, structure, and function of oligo(3-hydroxyalkanoates): contributions by synthetic organic chemists.

@article{Seebach1999DetectionSS,
  title={Detection, synthesis, structure, and function of oligo(3-hydroxyalkanoates): contributions by synthetic organic chemists.},
  author={Dieter Seebach and Monica G. Fritz},
  journal={International journal of biological macromolecules},
  year={1999},
  volume={25 1-3},
  pages={
          217-36
        }
}
  • D. Seebach, M. G. Fritz
  • Published 1 June 1999
  • Biology, Chemistry
  • International journal of biological macromolecules
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77 Citations
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Isolation and structure determination of complexed poly(3-hydroxyalkanoate) from beet (Beta vulgaris L.).
TLDR
In this study, a cPHA-component derived from a complex with calcium polyphosphate was isolated from sugar beet and determined to be a homopolymer composed of 3-hydroxybutyrate, and the polymerization mechanism of beetcPHA is discussed.
The Role of Short-Chain Conjugated Poly-(R)-3-Hydroxybutyrate (cPHB) in Protein Folding
  • R. Reusch
  • Biology
    International journal of molecular sciences
  • 2013
TLDR
The physical properties of cPHB indicate it plays important roles in the targeting and folding of c PHB-proteins, and its influence on the folding and structure of outer membrane protein A of Escherichia coli is discussed.
Molecular design and biosynthesis of biodegradable polyesters
The last two decades have witnessed major discoveries in the field of bacterial polyesters, which makes it all the more promising as a potential biodegradable and biocompatible material. Based on the…
Importance of oligo-R-3-hydroxybutyrates to S. lividans KcsA channel structure and function.
In the polyphosphate model of the Streptomyces lividans potassium channel KcsA, four polypeptides, each covalently modified by oligo-(R)-3-hydroxybutyrates (cOHB), surround a core molecule of…
Preparation of Free and of Specifically Protected Oligo[β‐Malic Acids] for Enzymatic Degradation Studies
TLDR
Enzymatic degradation experiments with the previously prepared cyclo-tetramer, the unprotected, and the O- or C-terminally protected samples of linear β-OMAs show that the enzyme from Physarum polycephalum is an exo-hydrolase cleaving the chain from theO-terminus.
Physiology, regulation, and limits of the synthesis of poly(3HB).
TLDR
Poly(3HB) is presented as a strategic survival polymer, and it is shown that growth-associated synthesis is not as rare as reported and the specific production rate and poly(3 HB) content appear to be more important than the yield coefficients.
Purification and Properties of an Intracellular 3-Hydroxybutyrate-Oligomer Hydrolase (PhaZ2) in Ralstonia eutropha H16 and Its Identification as a Novel Intracellular Poly(3-Hydroxybutyrate) Depolymerase
TLDR
Results indicate that PhaZ2 is a novel iPHB depolymerase, which participates in the mobilization of PHB in R. eutropha along withPhaZ1, which was found to bind to PHB inclusion bodies and as a soluble enzyme to cell-free supernatant fractions in Ralstonia eUTropha.
Oligo-3-hydroxybutyrates as potential carriers for drug delivery.
In vitro effect of oligo-hydroxyalkanoates on the growth of mouse fibroblast cell line L929.
Synthesis and NMR Analysis in Solution of Oligo(3‐hydroxyalkanoic acid) Derivatives with the Side Chains of Alanine, Valine, and Leucine (β‐Depsides): Coming Full Circle from PHB to β‐Peptides to PHB
TLDR
The extremely high flexibility (averaged or ‘random-coil' conformation) of the polyester chain (CO−O rotational barrier ca. 13 kcal/mol; no hydrogen bonding) has been demonstrated once again.
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References

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Poly(hydroxyalkanoates): A Fifth Class of Physiologically Important Organic Biopolymers?†
TLDR
One example of the contributions that synthetic organic chemists can make to important biological problems in an interdisciplinary framework is described, which led to the postulation of a P(3-HB) ion channel through the cell wall.
Preparation, Structure, and Properties of All Possible Cyclic Dimers (Diolides) of 3-Hydroxybutanoic Acid
In connection with the proposed structure of a trans-membrane cellular ion channel consisting of a complex between poly[(R)-3-hydroxy butanoate] (P(3-HB)) and calcium polyphosphate, CaPPi (ca. 150…
Investigation of the enzymatic cleavage of diastereomeric oligo(3-hydroxybutanoates) containing two to eight HB units. A model for the stereoselectivity of PHB depolymerase from Alcaligenes faecalis T1
TLDR
A titristat/HPLC method has been developed for following the degradation of oligo(3-hydroxybutanoates), OHBs, providing baseline separation for OHB methyl esters up to at least the octamers and proposing more detailed structural features at the binding site of the depolymerase.
Synthesis and Enzymatic Degradation of Dendrimers from (R)‐3‐Hydroxybutanoic Acid and Trimesic Acid
Dendrimers are attracting growing interest for use in stereoselective synthesis,['] as a new type of material,[21 and in biological studies, for example as DNA carriers.[31 We now report on the first…
Biodegradation of cyclic and substituted linear oligomers of poly(3-hydroxybutyrate).
TLDR
Biodegradation was prevented when the hydroxy terminus was protected by the FMOC group, but was not dependent on a free hydroxy terminal group; all other protecting groups did not prevent degradation.
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),…
Degradation of poly(3-hydroxybutyrate) by poly(3-hydroxybutyrate) depolymerase from Alcaligenes faecalis T1.
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.
Putative structure and functions of a poly-beta-hydroxybutyrate/calcium polyphosphate channel in bacterial plasma membranes.
  • R. Reusch, H. Sadoff
  • Biology
    Proceedings of the National Academy of Sciences of the United States of America
  • 1988
TLDR
It is proposed that the polyhydroxybutyrate forms an exolipophilic-endopolarophilic helix around an inner framework helix of calcium polyphosphate that forms a channel through the membrane and may play a role in the transport of calcium, phosphate, and DNA.
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…
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