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  1. Article ; Online: Peptide Stereochemistry Effects from p

    Adorinni, Simone / Gentile, Serena / Bellotto, Ottavia / Kralj, Slavko / Parisi, Evelina / Cringoli, Maria C / Deganutti, Caterina / Malloci, Giuliano / Piccirilli, Federica / Pengo, Paolo / Vaccari, Lisa / Geremia, Silvano / Vargiu, Attilio V / De Zorzi, Rita / Marchesan, Silvia

    ACS nano

    2024  Volume 18, Issue 4, Page(s) 3011–3022

    Abstract: The divergent supramolecular behavior of a series of tripeptide stereoisomers was elucidated through spectroscopic, microscopic, crystallographic, and computational techniques. Only two epimers were able to effectively self-organize into amphipathic ... ...

    Abstract The divergent supramolecular behavior of a series of tripeptide stereoisomers was elucidated through spectroscopic, microscopic, crystallographic, and computational techniques. Only two epimers were able to effectively self-organize into amphipathic structures, leading to supramolecular hydrogels or crystals, respectively. Despite the similarity between the two peptides' turn conformations, stereoconfiguration led to different abilities to engage in intramolecular hydrogen bonding. Self-assembly further shifted the p
    MeSH term(s) Hydrogels/chemistry ; Gold/chemistry ; Metal Nanoparticles/chemistry ; Peptides/chemistry
    Chemical Substances Hydrogels ; Gold (7440-57-5) ; Peptides
    Language English
    Publishing date 2024-01-18
    Publishing country United States
    Document type Journal Article
    ISSN 1936-086X
    ISSN (online) 1936-086X
    DOI 10.1021/acsnano.3c08004
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Azelaic Acid: A Bio-Based Building Block for Biodegradable Polymers.

    Todea, Anamaria / Deganutti, Caterina / Spennato, Mariachiara / Asaro, Fioretta / Zingone, Guglielmo / Milizia, Tiziana / Gardossi, Lucia

    Polymers

    2021  Volume 13, Issue 23

    Abstract: Azelaic acid is a dicarboxylic acid containing nine C atoms, industrially obtained from oleic acid. Besides its important properties and pharmacological applications, as an individual compound, azelaic acid has proved to be a valuable bio-based monomer ... ...

    Abstract Azelaic acid is a dicarboxylic acid containing nine C atoms, industrially obtained from oleic acid. Besides its important properties and pharmacological applications, as an individual compound, azelaic acid has proved to be a valuable bio-based monomer for the synthesis of biodegradable and sustainable polymers, plasticizers and lubricants. This review discusses the studies and the state of the art in the field of the production of azelaic acid from oleic acid, the chemical and enzymatic synthesis of bio-based oligo and polyester and their properties, including biodegradability and biocompostability.
    Language English
    Publishing date 2021-11-24
    Publishing country Switzerland
    Document type Journal Article ; Review
    ZDB-ID 2527146-5
    ISSN 2073-4360 ; 2073-4360
    ISSN (online) 2073-4360
    ISSN 2073-4360
    DOI 10.3390/polym13234091
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Heterochirality and Halogenation Control Phe-Phe Hierarchical Assembly.

    Kralj, Slavko / Bellotto, Ottavia / Parisi, Evelina / Garcia, Ana M / Iglesias, Daniel / Semeraro, Sabrina / Deganutti, Caterina / D'Andrea, Paola / Vargiu, Attilio V / Geremia, Silvano / De Zorzi, Rita / Marchesan, Silvia

    ACS nano

    2020  Volume 14, Issue 12, Page(s) 16951–16961

    Abstract: Diphenylalanine is an amyloidogenic building block that can form a versatile array of supramolecular materials. Its shortcomings, however, include the uncontrolled hierarchical assembly into microtubes of heterogeneous size distribution and well-known ... ...

    Abstract Diphenylalanine is an amyloidogenic building block that can form a versatile array of supramolecular materials. Its shortcomings, however, include the uncontrolled hierarchical assembly into microtubes of heterogeneous size distribution and well-known cytotoxicity. This study rationalized heterochirality as a successful strategy to address both of these pitfalls and it provided an unprotected heterochiral dipeptide that self-organized into a homogeneous and optically clear hydrogel with excellent ability to sustain fibroblast cell proliferation and viability. Substitution of one l-amino acid with its d-enantiomer preserved the ability of the dipeptide to self-organize into nanotubes, as shown by single-crystal XRD analysis, whereby the pattern of electrostatic and hydrogen bonding interactions of the backbone was unaltered. The effect of heterochirality was manifested in subtle changes in the positioning of the aromatic side chains, which resulted in weaker intermolecular interactions between nanotubes. As a result, d-Phe-l-Phe self-organized into homogeneous nanofibrils with a diameter of 4 nm, corresponding to two layers of peptides around a water channel, and yielded a transparent hydrogel. In contrast with homochiral Phe-Phe stereoisomer, it formed stable hydrogels thermoreversibly. d-Phe-l-Phe displayed no amyloid toxicity in cell cultures with fibroblast cells proliferating in high numbers and viability on this biomaterial, marking it as a preferred substrate over tissue-culture plastic. Halogenation also enabled the tailoring of d-Phe-l-Phe self-organization. Fluorination allowed analogous supramolecular packing as confirmed by XRD, thus nanotube formation, and gave intermediate levels of bundling. In contrast, iodination was the most effective strategy to augment the stability of the resulting hydrogel, although at the expense of optical transparency and biocompatibility. Interestingly, iodine presence hindered the supramolecular packing into nanotubes, resulting instead into amphipathic layers of stacked peptides without the occurrence of halogen bonding. By unravelling fine details to control these materials at the meso- and macro-scale, this study significantly advanced our understanding of these systems.
    Language English
    Publishing date 2020-11-11
    Publishing country United States
    Document type Journal Article
    ISSN 1936-086X
    ISSN (online) 1936-086X
    DOI 10.1021/acsnano.0c06041
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article: Microwave-Assisted Cyclization of Unprotected Dipeptides in Water to 2,5-Piperazinediones and Self-Assembly Study of Products­ and Reagents

    Kurbasic, Marina / Semeraro, Sabrina / Garcia, Ana M. / Kralj, Slavko / Parisi, Evelina / Deganutti, Caterina / De Zorzi, Rita / Marchesan, Silvia

    Synthesis

    2019  Volume 51, Issue 14, Page(s) 2829–2838

    Abstract: Dipeptides and their cyclized 2,5-piperazinedione (or diketopiperazine, DKP) derivatives are attractive building blocks for supra­molecular hydrogels. The Phe-Phe, ( p -nitro)-Phe-Phe, and Phe-Val dipeptides and their corresponding DKPs are studied for ... ...

    Abstract Dipeptides and their cyclized 2,5-piperazinedione (or diketopiperazine, DKP) derivatives are attractive building blocks for supra­molecular hydrogels. The Phe-Phe, ( p -nitro)-Phe-Phe, and Phe-Val dipeptides and their corresponding DKPs are studied for self-assembly in water. The DKPs were obtained in high yields by microwave-assisted cyclization­ of the dipeptides in water, demonstrating that use of their methyl ester derivatives as reported in the literature is not necessary for successful cyclization. Single-crystal XRD structures are reported for two DKPs as well as stable hydrogels at neutral pH.
    Keywords dipeptide ; diketopiperazine ; self-assembly ; hydrogels ; amyloid­ ; microwaves ; 2,5-piperazinedione
    Language English
    Publishing date 2019-03-25
    Publisher © Georg Thieme Verlag
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2033062-5
    ISSN 1437-210X ; 0039-7881
    ISSN (online) 1437-210X
    ISSN 0039-7881
    DOI 10.1055/s-0037-1612376
    Database Thieme publisher's database

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