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  • 1. Georgsson, J
    et al.
    Hallberg, A
    Larhed, M
    Rapid palladium-catalyzed synthesis of esters from aryl halides utilizing Mo(CO)(6) as a solid carbon monoxide source2003In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 5, no 4, p. 350-352Article in journal (Refereed)
  • 2.
    Johansson, Anja
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Åkerblom, Eva
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Ersmark, Karolina
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Lindeberg, Gunnar
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    An Improved Procedure for N- to C-Directed (Inverse) Solid-Phase Peptide Synthesis2000In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 2, no 5, p. 496-507Article in journal (Refereed)
    Abstract [en]

    A method for solid-phase peptide synthesis in the N- to C-direction that delivers good coupling yields and a low degree of epimerization is reported. The optimized method involves the coupling, without preactivation, of the resin-bound C-terminal amino acid with excess amounts of amino acid tri-tert-butoxysilyl (Sil) esters, using HATU as coupling reagent and 2,4,6-trimethylpyridine (TMP, collidine) as a base. For the amino acids investigated, the degree of epimerization was typically 5%, except for Ser(t-Bu) which was more easily epimerized (ca. 20%). Five tripeptides (AA(1)-AA(2)-AA(3)) with different properties were used as representative model peptides in the development of the synthetic method: Asp-Leu-Glu, Leu-Ala-Phe, Glu-Asp-Val, Asp-Ser-Ile, and Asp-D-Glu-Leu. The study used different combinations of HATU and TBTU as activating agents, N, N-diisopropylethylamine (DIEA) and TMP as bases, DMF and dichloromethane as solvents, and cupric chloride as an epimerization suppressant. The epimerization of AA(2) in the coupling of AA(3) was further reduced in the presence of cupric chloride. However, the use of this reagent also resulted in a decrease in loading onto the resin and significant cleavage between AA(1) and AA(2). Experiments indicated that the observed suppressing effect of cupric chloride on epimerization in the present system merely seemed to be a result of a base-induced cleavage of the oxazolone system, the key intermediate in the epimerization process. Consequently, the cleavages were most pronounced in slow couplings. An improved synthesis of fully characterized amino acid tri-tert-butoxysilyl (Sil) ester hydrochloride building blocks is presented. The amino acid Sil esters were found to be stable as hydrochlorides but not as free bases. Although only a few peptides have been used in this study, we believe that the facile procedure devised herein should provide an attractive alternative for the solid-phase synthesis of short (six residues or less) C-terminally modified peptides, e.g., in library format.

  • 3. Kaiser, N F K
    et al.
    Hallberg, A
    Larhed, M
    In situ generation of carbon monoxide from solid molybdenum hexacarbonyl. A convenient and fast route to palladium-catalyzed carbonylation reactions2002In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 4, no 2, p. 109-111Article in journal (Refereed)
  • 4.
    Nöteberg, Daniel
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Schaal, Wesley
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Hamelink, Elizabeth
    Vrang, Lotta
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    High-speed optimization of inhibitors of the malarial proteases plasmepsin I and II2003In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 5, no 4, p. 456-464Article in journal (Refereed)
    Abstract [en]

    Four focused libraries targeted for inhibition of the malarial proteases plasmepsin I and II were designed, synthesized, purified, and screened. Selected carboxylic acids and organometallic reactants with diverse physical properties were attached to the hydroxylethylamine scaffold in the P3 and P1‘ positions to furnish inhibitors with highly improved activity. The concept of controlled and sequential microwave heating was employed for rapid library generation. This combinatorial optimization protocol afforded plasmepsin inhibitors not only with Ki values in the low nanomolar range, but also with high selectivity versus the human protease cathepsin D. With this class of inhibitory agents, modifications of the P1‘ substituents resulted in the largest impact on the plasmepsin/cathepsin D selectivity.

  • 5.
    Röttger, Svenja
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Sjöberg, Per J. R.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Microwave-Enhanced Copper-Catalyzed N-Arylation of Free and Protected Amino Acids in Water2007In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 9, no 2, p. 204-209Article in journal (Refereed)
    Abstract [en]

    A microwave-enhanced copper-catalyzed protocol for N-arylation using water as the solvent is reported. This fast transformation allows the reaction between various amino acids or amino acid esters and a diverse set of substituted aryl bromides in less than 40 min, affording good yields of non-protected N-arylated amino acids with only minor racemization (6% or less). In addition, online ESI-MS and MS/MS analysis were used to "fish-out" an anionic Cu-containing amino acid complex directly from an ongoing N-arylation reaction.

  • 6. Wan, Y Q
    et al.
    Alterman, M
    Larhed, M
    Hallberg, A
    Formamide as a combined ammonia synthon and carbon monoxide source in fast palladium-catalyzed aminocarbonylations of aryl halides2003In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 5, no 2, p. 82-84Article in journal (Refereed)
  • 7.
    Wannberg, Johan
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Dallinger, Doris
    Kappe, C. Oliver
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Microwave-Enhanced and Metal-Catalyzed Functionalizations of the 4-Aryl-Dihydropyrimidone Template2005In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 7, no 4, p. 574-583Article in journal (Refereed)
    Abstract [en]

    Progress in organometallic catalysis and recent advancements in the development of carbonylative reaction protocols without direct use of carbon monoxide have been utilized for efficient functionalizations of 4-aryl-dihydropyrimidone structures. The use of modern microwave technology enabled both high reaction rates and convenient handling. Examples of palladium-catalyzed cross-couplings, Heck reactions, amino- and alkoxycarbonylations, and direct N-amidations of 4-(bromophenyl)-dihydropyrimidones were performed. Further, the first N3-arylations of the dihydropyrimidone ring system were successfully completed using the copper-catalyzed Goldberg reaction. Altogether, these protocols provide new tools for rapid generation of novel and diverse dihydropyrimidone derivatives.

  • 8.
    Wannberg, Johan
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Kaiser, Nils-Fredrik K.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Vrang, Lotta
    Samuelsson, Bertil
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    High-Speed Synthesis of Potent C2-Symmetric HIV-1 Protease Inhibitors by in Situ Aminocarbonylations2005In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 7, no 4, p. 611-617Article in journal (Refereed)
    Abstract [en]

    Two novel series of C2-symmetric HIV-1 protease inhibitors were synthesized by microwave-promoted, palladium-catalyzed aminocarbonylations of the o-iodo- and m-bromobenzyloxy P1/P1' substituted core structures. Molybdenum hexacarbonyl was used as a convenient solid source of carbon monoxide in these transformations. After the initial high-speed library generation, biological testing identified highly active HIV-1 protease inhibitors. Selected ortho- and meta-decorated inhibitors were subsequently resynthesized on a larger scale and retested for their affinity toward HIV-1 protease, showing micromolar to low nanomolar inhibition. The discovery of highly active inhibitors containing large phenyl amide ortho substituents in the P1/P1' positions indicates that larger groups than previously believed are tolerated in this part of the S1/S1' pocket.

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