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  1. Article ; Online: Stable D-xylose ditriflate in divergent syntheses of dihydroxy prolines, pyrrolidines, tetrahydrofuran-2-carboxylic acids, and cyclic β-amino acids.

    Balo, Rosalino / Fernández, Alberto G / Chopdat, Adam / Ayadi, Soufian El / Kato, Atsushi / Estévez, Ramón J / Fleet, George W J / Estévez, Juan C

    Organic & biomolecular chemistry

    2022  Volume 20, Issue 47, Page(s) 9447–9459

    Abstract: Double nucleophilic displacement of D-xylo-ditriflate by amines, water and alkyl cyanoacetates, respectively, gave a series of bicyclic divergent intermediates for the synthesis of a wide range of highly functionalized targets, including hydroxylated ... ...

    Abstract Double nucleophilic displacement of D-xylo-ditriflate by amines, water and alkyl cyanoacetates, respectively, gave a series of bicyclic divergent intermediates for the synthesis of a wide range of highly functionalized targets, including hydroxylated prolines, pyrrolidines, furanoic acids, and cyclopentanes.
    MeSH term(s) Proline ; Pyrrolidines ; Xylose ; Carboxylic Acids
    Chemical Substances Proline (9DLQ4CIU6V) ; Pyrrolidines ; Xylose (A1TA934AKO) ; Carboxylic Acids
    Language English
    Publishing date 2022-12-07
    Publishing country England
    Document type Journal Article
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d2ob01255c
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Polyhydroxylated Cyclopentane β-Amino Acids Derived from d-Mannose and d-Galactose: Synthesis and Protocol for Incorporation into Peptides.

    Fernández, Fernando / Fernández, Alberto G / Balo, Rosalino / Sánchez-Pedregal, Víctor M / Royo, Miriam / Soengas, Raquel G / Estévez, Ramón J / Estévez, Juan C

    ACS omega

    2022  Volume 7, Issue 2, Page(s) 2002–2014

    Abstract: A stereoselective synthesis of polyhydroxylated cyclopentane β-amino acids from hexoses is reported. The reaction sequence comprises, as key steps, ring-closing metathesis of a polysubstituted diene intermediate followed by the stereoselective aza- ... ...

    Abstract A stereoselective synthesis of polyhydroxylated cyclopentane β-amino acids from hexoses is reported. The reaction sequence comprises, as key steps, ring-closing metathesis of a polysubstituted diene intermediate followed by the stereoselective aza-Michael functionalization of the resulting cyclopent-1-ene-1-carboxylic acid ester. Examples of synthesis of polysubstituted 2-aminocyclopentanecarboxylic acid derivatives starting from protected d-mannose and d-galactose are presented. A general protocol for the incorporation of these highly functionalized alicyclic β-amino acids into peptides is also reported.
    Language English
    Publishing date 2022-01-04
    Publishing country United States
    Document type Journal Article
    ISSN 2470-1343
    ISSN (online) 2470-1343
    DOI 10.1021/acsomega.1c05468
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: β-Peptides incorporating polyhydroxylated cyclohexane β-amino acid: synthesis and conformational study.

    Reza, David / Balo, Rosalino / Otero, José M / Fletcher, Ai M / García-Fandino, Rebeca / Sánchez-Pedregal, Víctor M / Davies, Stephen G / Estévez, Ramón J / Estévez, Juan C

    Organic & biomolecular chemistry

    2023  Volume 21, Issue 42, Page(s) 8535–8547

    Abstract: We describe the synthesis of trihydroxylated cyclohexane β-amino acids from (-)-shikimic acid, in ... ...

    Abstract We describe the synthesis of trihydroxylated cyclohexane β-amino acids from (-)-shikimic acid, in their
    MeSH term(s) Amino Acids/chemistry ; Peptides/chemistry ; Cyclohexanecarboxylic Acids ; Protein Structure, Secondary
    Chemical Substances Amino Acids ; 2-aminocyclohexanecarboxylic acid (5691-19-0) ; Peptides ; Cyclohexanecarboxylic Acids
    Language English
    Publishing date 2023-11-01
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d3ob00906h
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Environmental Effects Determine the Structure of Potential β-Amino Acid Based Foldamers.

    Sussman, Fredy / Sánchez-Pedregal, Víctor M / Estévez, Juan C / Balo, Rosalino / Jiménez-Barbero, Jesús / Ardá, Ana / Gimeno, Ana / Royo, Miriam / Villaverde, M Carmen / Estévez, Ramón J

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2018  Volume 24, Issue 42, Page(s) 10625–10629

    Abstract: This work shows that hybrid peptides formed by alternating trans-2-aminocyclopentanecarboxylic acid (trans-ACPC) and trans-2-aminocyclohexanecarboxylic acid (trans-ACHC) do not fold in the solvents typically used in the study of their homo-oligomers. ... ...

    Abstract This work shows that hybrid peptides formed by alternating trans-2-aminocyclopentanecarboxylic acid (trans-ACPC) and trans-2-aminocyclohexanecarboxylic acid (trans-ACHC) do not fold in the solvents typically used in the study of their homo-oligomers. Only when the peptides are assayed in SDS micelles are the predicted helical structures obtained. This indicates that the environment could play an equally important role (as the backbone stereochemistry) in determining their fold, possibly by providing a sequestered environment.
    MeSH term(s) Amino Acids, Basic ; Cycloleucine/chemistry ; Peptides/chemistry ; Solvents/chemistry
    Chemical Substances Amino Acids, Basic ; Peptides ; Solvents ; Cycloleucine (0TQU7668EI)
    Language English
    Publishing date 2018-06-29
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-x
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.201801953
    Database MEDical Literature Analysis and Retrieval System OnLINE

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