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  • 1.
    Alpe, Marianne
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of oligosaccharides related to the capsular polysaccharides of Streptococcus pneumoniae serotype 9 and of Cryptococcus neoformans2003Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    In the present investigation, synthesis of oligosaccharides corresponding to structural elements present in the capsular polysaccharides of Streptococcus pneumoniae and Cryptococcus neoformans has been achieved. The first two sections describe the synthesis of spacer-equipped oligosaccharides corresponding to structures from the CPS of Streptococcus pneumoniae serotypes 9N, 9A and 9L, the production of which involved synthetic challenges such as the construction of β-ManNAc and α-GlcA linkages. The former challenge was met by employing azide displacement of a 2-O-triflate substituent on a β-glucoside, whereas the latter task was accomplished utilizing thioethyl glucuronic acid donors in the presence of various promoters. The pentasaccharide product obtained correspond to the complete repeating unit of the CPS of serotype 9A.

    The last two sections of this thesis describe the construction of thioglycoside di- and trisaccharide building blocks containing α-Man, β-Xyl, β-GlcA and 6-O-acetyl motifs, as well as subsequent assembly of these building blocks into oligosaccharides corresponding to the repeating units of the capsular polysaccharide of the yeast Cryptococcus neoformans. The GlcA moiety was introduced via trichloroacetimidate coupling involving the peracetylated glucuronic acid methyl ester donor, after which the subsequent necessary benzylation was performed with the di- and trisaccharides. All of the target oligosaccharides were synthesized as amino-spacer glycosides in order to make conjugation to a carrier protein possible.

  • 2.
    Edin, Michaela
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    On the mechanism of the unexpected facile formation of meso-diacetate products in enzymatic acetylation of alkanediols2003In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 68, p. 2216-2222Article in journal (Refereed)
  • 3. Kapoor, Mili
    et al.
    Srinivas, Honnappa
    Kandiah, Eaazhisai
    Gemma, Emiliano
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ellgaard, Lars
    Oscarson, Stefan
    Helenius, Ari
    Surolia, Avadhesha
    Interactions of Substrate with Calreticulin, an Endoplasmic Reticulum Chaperone2003In: Journal of Biological Chemistry, ISSN 0021-9258, E-ISSN 1083-351X, Vol. 278, no 8, p. 6194–6200-Article in journal (Refereed)
  • 4.
    Lindquist, Charlotta
    et al.
    Organisk kemi, Avdelningen för kemi, KTH.
    Ulf Tedebark,
    Oguz Ersoy,
    Peter Somfai,
    Microwave-Assisted Coupling of Carboxylic Acids to a Polymer Bound Hydrazine Linker2003In: Synthetic Communications, ISSN 0039-7911, E-ISSN 1532-2432, Vol. 33, no 13, p. 2257-2262Article in journal (Refereed)
    Abstract [en]

    A set of carboxylic acids, all being potential scaffolds for combinatorial chemistry or peptide synthesis, were coupled to a polymer bound aryl hydrazine linker using microwave irradiation in good yields. Improved yields and reduced reaction times were achieved byusing microwave-assisted heating compared to conventional heating.

  • 5. Marsh, Göran
    Polybrominated diphenyl ethers and their hydroxy and methoxy derivatives: congener specific synthesis and analysis2003Doctoral thesis, comprehensive summary (Other academic)
  • 6. Mohan, Halasayam
    et al.
    Gemma, Emiliano
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ruda, Katinka
    Oscarson, Stefan
    Efficient Synthesis of Spacer-linked Dimers of N-Acetyllactosamine Using Microvawe-assisted Pyridinium Triflate-promoted Glycosylations with Oxazoline Donors2003In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, no 9, p. 1255-1256Article in journal (Refereed)
  • 7.
    Olofsson, Berit
    et al.
    Royal Institute of Technology, Sweden.
    Somfai, Peter.
    Royal Institute of Technology, Sweden.
    Determination of the relative configuration of vic-amino alcohols2003In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 44, no 6, p. 1279-1281Article in journal (Refereed)
    Abstract [en]

    A large set of syn- and anti-1,2-amino alcs. has been synthesized. Upon comparison of the CHO and CHN 1H NMR shifts a general trend has been obsd., making it possible to det. the relative configuration of 1,2-amino alcs. without derivatization or shift reagents.

  • 8.
    Olofsson, Berit
    et al.
    Royal Institute of Technology, Sweden.
    Somfai, Peter
    Royal Institute of Technology, Sweden.
    Divergent Synthesis of D-erythro-Sphingosine, L-threo-Sphingosine, and Their Regioisomers2003In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 68, no 6, p. 2514-2517Article in journal (Refereed)
    Abstract [en]

    Starting from a vinyl epoxide, a divergent synthesis of four sphingosine isomers is described. The remaining four isomers can easily be synthesized using the same methodol. Although numerous syntheses of sphingosine have been published, this is the first general route leading to all eight isomers in this important compd. class. The synthetic strategy relies on regioselective opening of a vinyl epoxide and a vinylaziridine in the allylic position.

  • 9.
    Segerstedt, Eva
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Approaches to the synthesis of candidate glycoconjugate vaccines against non-typeable Haemophilus influenzae2003Doctoral thesis, comprehensive summary (Other academic)
  • 10.
    Zmudzka, Katarzyna
    et al.
    Polish Acad Sci, Ctr Mol & Macromol Studies.
    Johansson, Tommy
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wojcik, Marzena
    Polish Acad Sci, Ctr Mol & Macromol Studies.
    Janicka, Magdalena
    Polish Acad Sci, Ctr Mol & Macromol Studies.
    Nowak, Marian
    Polish Acad Sci, Ctr Mol & Macromol Studies.
    Stawinski, Jacek
    Nawrot, Barbara
    Polish Acad Sci, Ctr Mol & Macromol Studies.
    Novel DNA Analogues with 2-, 3- and 4-Pyridylphosphonate Internucleotide Bonds: Synthesis and Hybridisation Properties2003In: New Journal of Chemistry, ISSN 1144-0546, Vol. 27, no 12, p. 1698-1705Article in journal (Refereed)
    Abstract [en]

    Oligothymidylates modified with stereodefined 2-pyridyl-, 3-pyridyl- and 4-pyridylphosphonate moieties at one or two juxtaposed internucleotide positions were prepared, and their avidity towards complementary single stranded DNA and RNA, as well as toward double stranded DNA were evaluated by UV melting temperature and CD studies. It was found that the sense of chirality at the phosphorus centre and the position of the nitrogen atom in the pyridyl ring of a pyridylphosphonate moiety are important factors governing stability of double- and triple-stranded complexes formed by these oligonucleotides. DNA/DNA and DNA/RNA duplexes containing oligothymidylate strands with R-P-pyridylphosphonate units differed only slightly from unmodified reference complexes. In contrast to this, the S-P-pyridylphosphonate derivatives exhibited lower binding affinity than both their R-P-counterparts and the unmodified reference oligonucleotide T-20. Triplexes of oligo(thymidyl pyridylphosphonate)s with hairpin oligomer d(A(21)C(4)T(21)) were found mostly to be thermodynamically slightly more stable in pH 7.4 and less stable in pH 5.0 than non-modified complexes. As expected, oligonucleotides with pyridylphosphonate internucleotide bonds were recognised by 3'- and 5'-exonucleases but the chimeric oligonucleotide chains were not cleaved at the modi. cation sites.

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