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  • 1.
    Blom, Magnus
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Olsson, Sandra
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Norrehed, Sara
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Andersson, Claes-Henrik
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Fysikalisk-organisk kemi.
    Grennberg, Helena
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Fysikalisk-organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi I.
    Photomodulable bis-porphyrin molecular tweezers as dynamic host systems for diamine guestsManuskript (preprint) (Övrigt vetenskapligt)
    Abstract [en]

    Bisporphyrin molecular tweezers with an enediyne (1) or a stiff stilbene (2) photoswitchable spacer are proposed as systems for modulation of bitopic binding to diamine guests via E/Z photoisomerization. The photoisomerization has been monitored by UV-Vis and 1H NMR spectroscopy and occurs without side reactions such as Bergman cyclization. Possible applications are rationalized in terms of competitive binding involving monoamine/diamine mixtures, and are supported by conformational analysis of the envisioned host-guest complexes. Binding dynamics for conformationally flexible guests show significantly different performance of aliphatic 1,w-diamine guests with varying N-N distance.

  • 2.
    Bunrit, Anon
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Dahlstrand, Christian
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Olsson, Sandra K.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Srifa, Pemikar
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Huang, Genping
    Orthaber, Andreas
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Molekylär biomimetik.
    Sjöberg, Per J. R.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Analytisk kemi.
    Biswas, Srijit
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Himo, Fahmi
    Samec, Joseph S. M.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Bronsted Acid-Catalyzed Intramolecular Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer2015Ingår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 137, nr 14, s. 4646-4649Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The hydroxyl group of enantioenriched benzyl, propargyl, allyl, and alkyl alcohols has been intramolecularly displaced by uncharged O-, N-, and S-centered nucleophiles to yield enantioenriched tetrahydrofuran, pyrrolidine, and tetrahydrothiophene derivatives with phosphinic acid catalysis. The five-membered heterocyclic products are generated in good to excellent yields, with high degree of chirality transfer, and water as the only side-product. Racemization experiments show that phosphinic acid does not promote S(N)1 reactivity. Density functional theory calculations corroborate a reaction pathway where the phosphinic acid operates as a bifunctional catalyst in the intramolecular substitution reaction. In this mechanism, the acidic proton of the phosphinic acid protonates the hydroxyl group, enhancing the leaving group ability. Simultaneously, the oxo group of phosphinic acid operates as a base abstracting the nucleophilic proton and thus enhancing the nucleophilicity. This reaction will open up new atom efficient techniques that enable alcohols to be used as nucleofuges in substitution reactions in the future.

  • 3.
    Bunrit, Anon
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Dahlstrand, Christian
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Srifa, Pemikar
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Olsson, Sandra K.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Huang, Genping
    Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden.;Tianjin Univ, Sch Sci, Dept Chem, Tianjin 300072, Peoples R China..
    Biswas, Srijit
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC. Ctr Biomed Res, Lucknow 226014, Uttar Pradesh, India..
    Himo, Fahmi
    Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden..
    Samec, Joseph S. M.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC. Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden..
    Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer2016Ingår i: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, Vol. 27, nr 2, s. 173-176Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A brief overview of the development of direct substitution of the hydroxyl (OH) group of alcohols in our research group is presented. By applying a BrOnsted acid, an intramolecular substitution of the OH group in stereogenic alcohols with chirality transfer was achieved. Noteworthy, the intramolecular substitution has a wide scope in respect to both the nucleophile and also the nucleofuge. A mechanistic study by both experiments and DFT calculations revealed a unique reaction pathway in which the BrOnsted acid operates in a bifunctional manner to promote an S(N)2-type reaction mechanism.

  • 4.
    Bunrit, Anon
    et al.
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    Watile, Rahul
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    Dahlstrand, Christian
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Olsson, Sandra
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Srifa, Pemikar
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    Huang, Genping
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    Biswas, Srijit
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Himo, Fahmi
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    Samec, Joseph
    Stockholm Univ, Organ Chem, Stockholm, Sweden..
    H3PO2-catalyzed intramolecular stereospecific nucleophilic substitution of the hydroxyl group in stereogenic alcohols2017Ingår i: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 254Artikel i tidskrift (Övrigt vetenskapligt)
  • 5.
    Olsson, Sandra
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Host-Guest Interactions for Structural Analysis of Organic Molecules: Development of new Tools for Stereochemical Characterization2019Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
    Abstract [en]

    The focus of this thesis is on the development of molecular tweezers as host-guest systems for stereochemical characterization of small organic molecules.

    There are two central problems to stereochemical characterization of small molecules. The first is that there are few methods for the determination of absolute stereochemistry and the complexity of the task increases with the number of chiral centres in the molecule. The second is the flexibility of small molecules. The data received from NMR spectroscopy, the standard method for structural characterization is an average of all conformers present in solution, making exact determination of the structure challenging if stereocenters are involved.

    This research group has previously developed two bis-porphyrin molecular tweezers that can be used as hosts for relative stereochemical determination by NMR (NAMFIS) by limiting the flexibility of the guest molecules and for absolute stereochemical determination Exciton-Coupled Circular Dichroism (ECCD) by providing suitable chromophores. However, the use of these tweezers was limited to diamine molecules.

    To extend the application of both tweezer host systems, a range of metalloporphyrins have been investigated both computationally and experimentally to identify candidates binding strongly to oxygen containing functional groups (Paper I). One of the porphyrins identified has been used to synthesise a new system with the potential to be used for relative stereochemical determination by NMR (NAMFIS) of molecules with a wide variety of functional groups (Paper IV).

    To further develop the systems, the photo-isomerization properties of the stiff stilbene linker of one of the tweezers has been investigated. Macrocyclic diether model compounds, incorporating the stiff stilbene linker have been used to show that the photo-isomerizability strongly is affected by molecular strain (Paper II). The results suggest that if paired with a suitable porphyrin (with no UV/Vis absorption overlap) a photo-switchable tweezer might be constructed.

    To map the guest range of the stiff stilbene linked tweezer it was found that this tweezer gives strong to moderate signals for monoamines with a rigid structure (Paper III). As ditopic binding is usually a requirement for an ECCD signal when using bis-porphyrin molecular tweezers, this is a discovery that should be of general interest.

    Delarbeten
    1. Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding
    Öppna denna publikation i ny flik eller fönster >>Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding
    2018 (Engelska)Ingår i: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 47, nr 33, s. 11572-11585Artikel i tidskrift (Refereegranskat) Published
    Abstract [en]

    By systematic measurements we have evaluated a series of tetraphenyl metalloporphyrins and halogenated tetraphenyl metalloporphyrin derivatives for binding to ligands with oxygen containing functional groups, using methanol, acetic acid and acetone as examples. Experimental binding constants identified three metalloporphyrins with good binding to all three ligands: MgTPFPP, MgTPPBr8 and ZnTPPBr8 as well as a range of porphyrins binding to select ligands. Based on these results the optimal porphyrins can be selected for the desired binding interactions. We also show how to use DFT calculations to evaluate the potential binding between a metalloporphyrin and a ligand, which is deduced from free energies of binding ΔG, charge transfer ΔQ, and change of metal spin state. Computations on unsubstituted porphyrins in lieu of tetraphenyl porphyrin systems yield reliable predictions of binding interactions with good correlation to the corresponding experimental data. The calculations have also yielded interesting insights into the effect of halogenation in the β-position on the binding to ligands with oxygen containing functional groups.

    Ort, förlag, år, upplaga, sidor
    Royal Society of Chemistry, 2018
    Nyckelord
    Porphyrins, DFT, host-guest
    Nationell ämneskategori
    Organisk kemi
    Forskningsämne
    Kemi med inriktning mot organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-359830 (URN)10.1039/c8dt02432d (DOI)000442509700031 ()30087966 (PubMedID)
    Forskningsfinansiär
    Vetenskapsrådet, 621-2012-3379Carl Tryggers stiftelse för vetenskaplig forskning , 16:156Swedish National Infrastructure for Computing (SNIC), 2018/3-240National Supercomputer Centre (NSC), Sweden, SNIC 2018/3-240
    Tillgänglig från: 2018-09-06 Skapad: 2018-09-06 Senast uppdaterad: 2019-04-23Bibliografiskt granskad
    2. Effect of Ring Size on Photoisomerization Properties of Stiff Stilbene macrocycles
    Öppna denna publikation i ny flik eller fönster >>Effect of Ring Size on Photoisomerization Properties of Stiff Stilbene macrocycles
    (Engelska)Manuskript (preprint) (Övrigt vetenskapligt)
    Abstract [en]

    A series of stiff stilbene macrocycles have been studied in order to investigate the possible impact of macrocycle ring size on their photo-dynamic properties. The results show that reducing the ring size counteracts the photoisomerization ability of the macrocycles. However, even the smallest macrocycle studied (stiff stilbene subunits linked by a six carbon chain) showed some degree of isomerization when irradiated. DFT calculations of the energy differences between the E- and Z-isomers show the same trend as the experimental results. Interestingly the DFT study highlights that the energy difference between the E- and Z-isomers of even the largest macrocycle (linked by a twelve carbon chain) is significantly higher than that of the stiff stilbene unit itself. This indicates that a flexible chain may significantly affect the efficiency of photoisomerizations.

    Nyckelord
    Stiff stilbene cyclic photoisomerization
    Nationell ämneskategori
    Organisk kemi
    Forskningsämne
    Kemi med inriktning mot organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-382215 (URN)
    Forskningsfinansiär
    Vetenskapsrådet, 621-2012-3379Carl Tryggers stiftelse för vetenskaplig forskning , CTS 16:156Swedish National Infrastructure for Computing (SNIC)
    Tillgänglig från: 2019-04-23 Skapad: 2019-04-23 Senast uppdaterad: 2019-04-23
    3. Exciton-Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host-Guest Complexes with a Bis(zinc porphyrin) Tweezer
    Öppna denna publikation i ny flik eller fönster >>Exciton-Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host-Guest Complexes with a Bis(zinc porphyrin) Tweezer
    2018 (Engelska)Ingår i: ChemPlusChem, ISSN 2192-6506, Vol. 83, s. 1169-1178Artikel i tidskrift (Refereegranskat) Published
    Abstract [en]

    A stiff-stilbene-linked bisporphyrin tweezer with inherent helicity was used for exciton-coupled circular dichroism (ECCD) characterization of a series of monotopically binding amine guest molecules. CD signals were observed for a variety of monoamines at relatively low tweezer/amine (host/guest) ratios between 1 :10 to 1: 70. For the amines producing the most intense CD signals, a binding stoichiometry of 1:2 was found. A likely explanation is the presence of guest-guest interactions in the complexes. This is supported by the correlation observed between CD signal intensity and magnitude of possible noncovalent binding between the guests, which can be divided into three groups showing no, moderate and strong response, respectively. Further support for this rationalization comes from molecular modelling.

    Ort, förlag, år, upplaga, sidor
    Weinheim: Wiley-VCH Verlagsgesellschaft, 2018
    Nyckelord
    bis-porphyrin tweezers, conformation analysis, exciton-coupled circular dichroism, host-guest systems, molecular modeling
    Nationell ämneskategori
    Organisk kemi
    Forskningsämne
    Kemi med inriktning mot organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-371629 (URN)10.1002/cplu.201800564 (DOI)000454527200013 ()
    Forskningsfinansiär
    Vetenskapsrådet, 621-2012-3379Carl Tryggers stiftelse för vetenskaplig forskning , CTS 16 : 156
    Tillgänglig från: 2018-12-21 Skapad: 2018-12-21 Senast uppdaterad: 2019-04-23Bibliografiskt granskad
    4. Synthesis of a novel bis-Mg-porphyrin tweezer
    Öppna denna publikation i ny flik eller fönster >>Synthesis of a novel bis-Mg-porphyrin tweezer
    (Engelska)Manuskript (preprint) (Övrigt vetenskapligt)
    Abstract [en]

    We have synthesised a novel semi-rigid bis-(magnesium-porphyrin) tweezer with a glycoluril backbone. meso-Tetrakis(pentafluorophenyl)porphyrin constitutes the two porphyrin units, each holding a magnesium(II) ion, and being connected to the glycoluril backbone via two -positions. This connection prevents any porphyrin rotation, leaving changes in gap size as sole conformational variation. Magnesium(II) tetrakis(pentafluorophenyl)porphyrin has in previous studies shown to bind well to both nitrogen-containing and oxygen-containing functional groups. The tweezer has the potential to retain this binding ability, which would be useful in the stereochemical characterization of small flexible molecules with multiple stereocentra and a wide variety of functional groups.

    Nyckelord
    magnesium-porphyrin tweezer synthesis
    Nationell ämneskategori
    Organisk kemi
    Forskningsämne
    Kemi med inriktning mot organisk kemi
    Identifikatorer
    urn:nbn:se:uu:diva-382217 (URN)
    Forskningsfinansiär
    Vetenskapsrådet, 621-2012-3379Carl Tryggers stiftelse för vetenskaplig forskning , CTS 16:156
    Tillgänglig från: 2019-04-23 Skapad: 2019-04-23 Senast uppdaterad: 2019-04-23
  • 6.
    Olsson, Sandra K.
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Benito Perez, Oscar
    Universitat de Barcelona.
    Blom, Magnus
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Effect of Ring Size on Photoisomerization Properties of Stiff Stilbene macrocyclesManuskript (preprint) (Övrigt vetenskapligt)
    Abstract [en]

    A series of stiff stilbene macrocycles have been studied in order to investigate the possible impact of macrocycle ring size on their photo-dynamic properties. The results show that reducing the ring size counteracts the photoisomerization ability of the macrocycles. However, even the smallest macrocycle studied (stiff stilbene subunits linked by a six carbon chain) showed some degree of isomerization when irradiated. DFT calculations of the energy differences between the E- and Z-isomers show the same trend as the experimental results. Interestingly the DFT study highlights that the energy difference between the E- and Z-isomers of even the largest macrocycle (linked by a twelve carbon chain) is significantly higher than that of the stiff stilbene unit itself. This indicates that a flexible chain may significantly affect the efficiency of photoisomerizations.

  • 7.
    Olsson, Sandra K.
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Dahlstrand, Christian
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding2018Ingår i: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 47, nr 33, s. 11572-11585Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    By systematic measurements we have evaluated a series of tetraphenyl metalloporphyrins and halogenated tetraphenyl metalloporphyrin derivatives for binding to ligands with oxygen containing functional groups, using methanol, acetic acid and acetone as examples. Experimental binding constants identified three metalloporphyrins with good binding to all three ligands: MgTPFPP, MgTPPBr8 and ZnTPPBr8 as well as a range of porphyrins binding to select ligands. Based on these results the optimal porphyrins can be selected for the desired binding interactions. We also show how to use DFT calculations to evaluate the potential binding between a metalloporphyrin and a ligand, which is deduced from free energies of binding ΔG, charge transfer ΔQ, and change of metal spin state. Computations on unsubstituted porphyrins in lieu of tetraphenyl porphyrin systems yield reliable predictions of binding interactions with good correlation to the corresponding experimental data. The calculations have also yielded interesting insights into the effect of halogenation in the β-position on the binding to ligands with oxygen containing functional groups.

  • 8.
    Olsson, Sandra K.
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Synthesis of a novel bis-Mg-porphyrin tweezerManuskript (preprint) (Övrigt vetenskapligt)
    Abstract [en]

    We have synthesised a novel semi-rigid bis-(magnesium-porphyrin) tweezer with a glycoluril backbone. meso-Tetrakis(pentafluorophenyl)porphyrin constitutes the two porphyrin units, each holding a magnesium(II) ion, and being connected to the glycoluril backbone via two -positions. This connection prevents any porphyrin rotation, leaving changes in gap size as sole conformational variation. Magnesium(II) tetrakis(pentafluorophenyl)porphyrin has in previous studies shown to bind well to both nitrogen-containing and oxygen-containing functional groups. The tweezer has the potential to retain this binding ability, which would be useful in the stereochemical characterization of small flexible molecules with multiple stereocentra and a wide variety of functional groups.

  • 9.
    Olsson, Sandra K.
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Schäfer, Clara
    Friedrich-Alexander-University Erlangen-Nürnberg.
    Blom, Magnus
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Organisk kemi.
    Exciton-Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host-Guest Complexes with a Bis(zinc porphyrin) Tweezer2018Ingår i: ChemPlusChem, ISSN 2192-6506, Vol. 83, s. 1169-1178Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A stiff-stilbene-linked bisporphyrin tweezer with inherent helicity was used for exciton-coupled circular dichroism (ECCD) characterization of a series of monotopically binding amine guest molecules. CD signals were observed for a variety of monoamines at relatively low tweezer/amine (host/guest) ratios between 1 :10 to 1: 70. For the amines producing the most intense CD signals, a binding stoichiometry of 1:2 was found. A likely explanation is the presence of guest-guest interactions in the complexes. This is supported by the correlation observed between CD signal intensity and magnitude of possible noncovalent binding between the guests, which can be divided into three groups showing no, moderate and strong response, respectively. Further support for this rationalization comes from molecular modelling.

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