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  • 1.
    Arvidsson, Per
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Frackenpohl, J
    Seebach, D
    Syntheses an CD-Spectroscopic Investigations of Longer-Chain B-Peptides: Preparation by Solid-Phase Couplings of Single Amino Acids, Dipeptides, and Tripeptides2003In: Helvetica Chemica Acta, no 86, p. 1552-1553Article in journal (Refereed)
  • 2.
    Arvidsson, Per
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Ryder, Neil S.
    Weiss, H. Markus
    Hook, David F.
    Escalante, Jaime
    Seebach, Dieter
    Exploring the Antibacterial and Hemolytic Activity of Shorter- and Longer-Chain B-, a,B-, and y-Peptides, and of B-Peptides from B2-3-Aza- and B3-2-Methylidene-amino Acids Bearing Proteinogenic Side Chains - A Survey2005In: Chemistry & Biodiversity, Vol. 2, p. 401-420Article in journal (Refereed)
    Abstract [en]

    The antibacterial activities of 31 different b-, mixed a/B-, and y-peptides, as well as of B-peptides derived from B2-3-aza- and B3-2-methylidene-amino acids were assayed against six pathogens (Enterococcus faecails, STaphylococcus aureus, Streptococcus pneumoniae, Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa), and the results were compared with literature data. The interaction of these peptides with mammalian cells, as modeled by measuring the hemolysis of human erythrocytes, was also investigated. In addition to those peptides designed to fold into amphiphilic helical conformations with positive charges on one face of the helix, one new peptide with hemolytic activity was detected within the sample set. Moreover, it was demontrated that neither cationic peptides used for membrane translocation (B3-oligoarginines), nor mixeda/B- or y-peptides with somatostatin-mimicking activities display unwanted hemolytic activity.

  • 3.
    Buttner, Frank
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. avd för organisk kemi.
    Norgren, Anna
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. avd för organisk kemi.
    Zhang, Suode
    Prabpai, Samran
    Kongsaeree, Palangpon
    Arvidsson, Per
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. avd för organisk kemi.
    Cyclic B-Tetra- and Pentapeptides: Synthesis through On-Resin Cyclization and Confomrational Studies by X-Ray, NMR and CD Spectroscopy and Theoretical Calculations2005In: Chem. Eur. J., Vol. 11, p. 6145-6158Article in journal (Refereed)
    Abstract [en]

    The solution-phase synthesis of the simplest cyclic B-tetrapeptide, cyclo(B-Ala)4 (4), as well as the solidphase syntheses through side chain anchoring and on-resin cyclization of the cyclic B3-tetrapeptide cyclo-(B3hPhe-B3hLeu-B3hLys-B3hGln-) (14) and the first cyclic B3-pentapeptide cyclo- (B3hVal-B3hPhe-B3Leu- B3hLys-B3hLys-) (19) are reported. Extensive computational as well as spectroscopic studies, including X-ray and NMR spectroscopy, were undertaken to determine the preferred conformations of these unnatural oligomers in solution and in the solid state. cyclo(B-Ala)4 (4) with no chiral side chains is shown to exist as a mixture of rapidly interchanging conformers in solution, whereas inclusion of chiral side chains in the cyclo-B3-tetrapetpride causes stabilizaton of one dominating conformer. The cyclic B3-pentapeptide on the other hand shows larger conformational freedom. The X-ray structure of achiral cyclo(B-Ala)4 (4) displays a Ci-symmetrical 16-membered ring with adjacent C=O and N-H atoms pointing pair wise up and down with respect to the ring plane. CD spectorscopic examinations of all cyclic B-peptides were undertaken and revealed results valuable as starting point for further structural investigations of these entities.

  • 4.
    Büttner, Frank
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Erdélyi, Máté
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Arvidsson, Per
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    cyclo(ß-Asp-ß3-hVal-ß3-hLys)-Solid-Phase Synthesis and Solution Structure of a Water Soluble ß-Tripeptide2004In: Helvetica Chimica Acta, Vol. 87, p. 2735-2741Article in journal (Refereed)
  • 5.
    Hedberg, Christian
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Källström, Klas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Arvidsson, Per
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Brandt, Peter
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Mechanistic Insights into the Phosphine-Free RuCp*-Diamine-Catalyzed Hydrogenation of Aryl Ketones: Experimental and Theoretical Evidence for an Alcohol-Mediated Dihydrogen Activation2005In: J. Am. Chem. Soc., no 127, p. 15083-15090Article in journal (Refereed)
    Abstract
  • 6.
    Norgren, Anna
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Zhang, Suode
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Arvidsson, Per
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Synthesis and circular dichroism spectroscopic investigations of oligomeric β-peptoids with α-chiral side chains2006In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 8, no 20, p. 4533-4536Article in journal (Refereed)
    Abstract [en]

    Biomimetic oligomers are of large interest both as targets for combinatorial and parallel synthetic efforts and as foldamers. For example, shorter peptoid derivatives of beta-peptides, i.e., oligo-N-substituted beta-Ala, have been described as potential lead structures. Herein, we describe a solid-phase synthetic route to beta-peptoids with alpha-chiral aromatic N-substituents up to 11 residues long. Furthermore, the folding propensities of these oligomers were investigated by circular dichroism (CD) spectroscopy.

  • 7.
    Zhang, Suode
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Avd för organisk kemi.
    Govender, Thavendran
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Avd för organisk kemi.
    Norström, Thomas
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Avd för organisk kemi.
    Arvidsson, Per
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Avd för organisk kemi.
    An Improved Synthesis of Fmoc-N-methyl-a-amino Acids2005In: J. Org. Chem., no 70, p. 6918-6920Article in journal (Refereed)
1 - 7 of 7
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