Optically active poly (\-malic-acid)

Guérin, Philippe; Vert, Michel; Braud, Christian; Lenz, Robert W.

doi:10.1007/bf00708479

Cited by 136 publications

(84 citation statements)

References 2 publications

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“…Material with a molecular mass of 10-12 kDa (the most abundant) was used in the present investigation. The methods used to synthesize poly(D,L-malate) and poly(L-malate) have been described [19,20] and were used here to generate samples of different molecular masses by slightly changing the experimental conditions. The biochemical properties of natural and synthetic poly(L-malate) were the same ([2], unpublished data).…”

Section: Experimental Procedures Materialsmentioning

confidence: 99%

Specific inhibition of Physarum polycephalum DNA‐polymerase‐α‐primase by poly(l‐malate) and related polyanions

Holler

Achhammer

Angerer

et al. 1992

European Journal of Biochemistry

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Poly(L-malate) is an unusual polyanion found in nuclei of plasmodia of Physarum polycephalum. We have investigated, by enzymatic and fluorimetric methods, whether poly(L-malate) and structurally related polyanions can interact with DNA-polymerase-a-primase complex and with histones of P. polycephalum. Poly(L-malate) is found to inhibit the activities of the DNA-polymerase-a-primase complex and to bind to histones. The mode of inhibition is competitive with regard to DNA in elongation and noncompetitive in the priming of DNA synthesis. Spermidine, spermine, and histones from P. polycephalum and from calf thymus bind to poly(L-malate) and antagonize the inhibition. The polyanions poly(viny1 sulfate), poly(acrylate), poly(L-malate), poly(D,L-malate), poly(L-aspartate), poly(L-glutamate) have been examined for their potency to inhibit the DNA polymerase. The degree of inhibition is found to depend on the distance between neighboring charges, given by the number of atoms (A') interspaced between them. Poly(L-malate) ( N = 5 ) and pOly(D,L-malate) ( N = 5 ) are the most efficient inhibitors, followed by poly(L-aspartate) ( N = 6), poly(acry1ate) ( N = 3), poly(Lglutamate) ( N = 8), poly(viny1 sulfate) ( N = 3). It is proposed that poly(L-malate) interacts with DNA-polymerase-a-primase of P. polycephalum. According to its physical and biochemical properties, poly(L-malate) may alternatively function as a molecular chaperone in nucleosome assembly in the S phase and as both an inhibitor and a stock-piling agent of DNA-polymerase-a-primase in the G 2 phase and M phase of the plasmodial cell cycle.Plasmodia1 cells of P. polycephalum have been of particular interest to cell biologists because of their giant multinucleated forms and their high synchrony in nuclear division [l]. In some instances, they resemble syncytically organized cells found during early stages of embryogenesis. P. polycephalum develops DNA polymerase a and newly replicated DNA may interact during the cell cycle competitively in such a way that DNA polymerase a is active during the S phase and inactive during the G2 phase. In this hypothesis, the initiation of histone synthesis marks the beginning of the S phase ([5], for a recent review about histones see [6]). The newly synthesized histones displace DNA polymerase CI from poly(L-malate) by competition. The released polymerase becomes involved in DNA replication until histone synthesis ceases, and histones are consumed in the energetically highly favorable formation of nucleosomes by newly replicated DNA. Free poly(L-malate) reassociates with DNA polymerase a at the onset of the G2 phase and thereby terminates DNA synthesis. Thus, poly(~-malate) may function in stock piling inactive DNA polymerase during the G 2 phase and M phase of the cell cycle. In the intact cell, DNA polymerase a is associated with DNA primase. Activities of these enzymes function coordinately during the start of DNA synthesis at replication origins and during initiation and elongation of Okazaki pieces (for a recent review see [...

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Section: Experimental Procedures Materialsmentioning

confidence: 99%

Specific inhibition of Physarum polycephalum DNA‐polymerase‐α‐primase by poly(l‐malate) and related polyanions

Holler

Achhammer

Angerer

et al. 1992

European Journal of Biochemistry

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“…The polymerization of 4-benzyloxycarbonyl-2-oxetanone, also called benzyl β-malolactonate (MLABz), requires first its synthesis and careful purifications. Since several synthetic procedures have already been published, 3,5,6,17 the preparation of racemic MLABz has been carried out according to the well-established "aspartic acid" route beginning with racemic aspartic acid (Scheme 1). 18 As previously reported for the synthesis of poly(β-malic acid)-bpoly(ε-caprolactone) diblock copolymers (PMLA-b-PCL), 10 a three-step strategy combining the anionic polymerization of benzyl β-malolactonate (MLABz) with the coordinative ring-opening polymerization (ROP) of (D,L)-lactide (LA), followed by the selective removal of benzyloxy protective groups, has been adopted for the synthesis of amphiphilic poly(β-malic acid)-bpolylactide (PMLA-b-PLA) diblock copolymers (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Benzyl β-malolactonate: synthesis, copolymerization and design of novel biodegradable macromolecular surfactants

Coulembier¹,

Ghisdal²,

Degée³

et al. 2006

Arkivoc

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Racemic [R,S] benzyl β-malolactonate monomer (MLABz) was synthesized according to the well-established "aspartic acid" route and purified to such an extend that it allowed the controlled synthesis of poly([R,S] β-malic acid)-b-poly((D,L)-lactide) diblock copolymers by a versatile three-step pathway combining anionic and coordination-insertion ROP of MLABz and lactide monomers, respectively. For the sake of comparison, amphiphilic poly([R,S] β-malic acid)-b-poly(ε-caprolactone) diblock copolymers of identical composition were synthesized as well. The associating behavior of monodisperse diblock copolymers consisting of water-soluble poly(β-malic acid) block and hydrophobic polylactide or poly(ε-caprolactone) block was studied in aqueous solution. Accordingly, both types of copolymers were dissolved directly in water and (dynamic) surface tension measurements were carried out. It came out that poly(β-malic acid)-bpoly((D,L)-lactide) amphiphilic diblock copolymers showed tensioactive properties with a lower critical micellar concentration, a higher efficiency of adsorption and a better monomer coefficient diffusion compared to corresponding poly(β-malic acid)-b-poly(ε-caprolactone) diblock copolymers of comparative composition.

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“…Optically active stereocopolymers of malic acid are accessible starting from L-or D-aspartic acid enantiomers [110] or L-or D-malic acid enantiomers [109] as chiral precursors. As mentioned above, a new family of synthetic and isotactic poly((S)-3,3-dimethylmalic acid) (chiral PDMMLA) is chemically prepared starting from L-(S)-malic acid.…”

Section: Synthesis Of Hydrophobic Pdmmlasmentioning

confidence: 99%

New promising biodegradable polyesters derived from poly((R,S)-3,3-dimethylmalic acid) for cardiovascular applications

Belibel¹,

Barbaud²

2017

Biodegradable Polymers: Recent Developments and New Perspectives

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Optically active poly (\-malic-acid)

Cited by 136 publications

References 2 publications

Specific inhibition of Physarum polycephalum DNA‐polymerase‐α‐primase by poly(l‐malate) and related polyanions

Specific inhibition of Physarum polycephalum DNA‐polymerase‐α‐primase by poly(l‐malate) and related polyanions

Benzyl β-malolactonate: synthesis, copolymerization and design of novel biodegradable macromolecular surfactants

New promising biodegradable polyesters derived from poly((R,S)-3,3-dimethylmalic acid) for cardiovascular applications

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