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  • 1.
    Angelin, Marcus
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Larsson, Rikard
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dynamic combinatorial resolution2009In: Dynamic Combinatorial Chemistry: In Drug Discovery, Bioorganic Chemistry, and Materials Science / [ed] Miller, B., John Wiley & Sons, 2009, p. 169-200Chapter in book (Refereed)
  • 2.
    Caraballo, Rémi
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Phosphine-Mediated Disulfide Metathesis in Aqueous Media2010In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 46, no 44, p. 8469-8471Article in journal (Refereed)
    Abstract [en]

    Dynamic carbohydrate systems have been efficiently generated through phosphine-mediated disulfide metathesis in aqueous media. The protein compatibility and binding features of the dynamic systems were demonstrated in situ using H-1 STD NMR.

  • 3.
    Caraballo, Rémi
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Towards Dynamic Drug Design: Identification and Optimization of β-Galactosidase Inhibitors from a Dynamic Hemithioacetal System2010In: ChemBioChem (Print), ISSN 1439-4227, E-ISSN 1439-7633, Vol. 11, no 11, p. 1600-1606Article in journal (Refereed)
    Abstract [en]

    A discovery strategy relying on the identification of fragments through resolution of a constitutional dynamic system, coupled to subsequent static ligand design and optimization, is demonstrated. The strategic design and synthesis of the best molecular fragments identified from a dynamic hemithioacetal system into static ligand structures yielded a range of -galactosidase inhibitors. Two series of structures mimicking the hemithioacetal motif were envisaged: thioglycosides and C-glycosides. Inhibition studies provided important structural information for the two groups, and 1-thiobenzyl--D-galactopyranoside demonstrated the best inhibitory effects.

  • 4.
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dynamic Systems: Evaluation, Screening and Synthetic Application2011Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The research work reported in the thesis deals with the development of dynamic covalent systems and their applications in evaluation and screening of protein-ligands and enzyme inhibitors, as well as in synthetic methodologies. The thesis is divided into four parts as described below.

    In part one, synthetic methodologies to access 3-functionalized phthalides and 3-thioisoindolinones using the concept of cascade reactions are demonstrated. Efficient syntheses of the target products are designed and performed in one-pot process under mild reaction conditions.

     In part two, phosphine-catalyzed disulfide metathesis for the generation of dynamic carbohydrate system in aqueous solution is demonstrated. In the presence of biological target (Concanavalin A), the optimal dynamic ligand is successfully identified in situ by the 1H STD-NMR spectroscopy.

    In part three, lipase-catalyzed resolutions of dynamic reversible systems using reversible cyanohydrin and hemithioacetal reactions in one-pot processes are demonstrated. The dynamic systems are generated under thermodynamic control in organic solution and subsequently resolved by lipase-mediated resolution under kinetic control. The resolution processes resulted in the lipase-selected substrates with high structural and stereochemical specificities.

    In the last part, dynamic fragment-based strategy is presented using β-galactosidase as a model target enzyme. Based on our previous study, the best dynamic inhibitor of β-galactosidase was identified using 1H STD-NMR technique from dynamic hemithioacetal systems. The structure of the dynamic inhibitor is tailored by fragment linking and optimization processes. The designed inhibitor structures are then synthesized and tested for inhibition activities against β-galactosidase. 

     

  • 5.
    Sakulsombat, Morakot
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Caraballo, Rémi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    A Dynamic Multicomponent Approach for One-Pot Synthesis of 3-Thioisoindolinones2013In: Israel Journal of Chemistry, ISSN 0021-2148, Vol. 53, no 1-2, p. 127-132Article in journal (Refereed)
    Abstract [en]

    A dynamic multicomponent reaction concept has been successfully applied to the syntheses of 3-thioisoindolinones and tricyclic gamma-lactams. The reactions were efficiently designed and operated in the absence of any catalyst under mild reaction conditions, resulting in the convenient variation of substituents on the N- and S-positions of the target products.

  • 6.
    Sakulsombat, Morakot
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Angelin, Marcus
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Tandem reversible addition-intramolecular lactonization for the synthesis of 3-functionalized phthalides2010In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 51, no 1, p. 75-78Article in journal (Refereed)
    Abstract [en]

    A new tandem process based on reversible nucleophilic addition and intramolecular lactonization of methyl 2-formylbenzoate leads to the efficient synthesis of 3-functionalized phthalides, which are important precursors for the synthesis of quinone skeletons via Hauser–Kraus annulation. The reactions are successfully carried out under mild conditions in single operations.

  • 7.
    Sakulsombat, Morakot
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Efficient Asymmetric Synthesis of 1-Cyano-tetrahydroisoquinolines from Lipase Dual Activity and Opposite Enantioselectivities in alpha-Aminonitrile Resolution2014In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 36, p. 11322-11325Article in journal (Refereed)
    Abstract [en]

    Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic alpha-aminonitrile compounds are described. alpha-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were shown to exhibit the dual catalytic activities, where opposite enantioselectivities could be recorded for certain substrates.

  • 8.
    Sakulsombat, Morakot
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    In Situ Evaluation of Lipase Performances Through Dynamic Asymmetric Cyanohydrin Resolution2011In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 9, no 4, p. 1112-1117Article in journal (Refereed)
    Abstract [en]

    A dynamic resolution process based on multiple reversible cyanohydrin formation coupled to lipase-mediated transesterification is demonstrated. The resulting process resulted in the efficient evaluation of complex lipase performances in asymmetric cyanohydrin acylate synthesis. Dynamic systems were generated and resolved in situ, and the effects of the reaction conditions could be directly monitored for the overall system. By this concept, the enzyme activity, chemo- and stereoselectivity for all involved substrates could be simultaneously evaluated.

  • 9.
    Sakulsombat, Morakot
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Zhang, Yan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dynamic Asymmetric Hemithioacetal Transformation by Lipase-Catalyzed gamma-Lactonization: In Situ Tandem Formation of 1,3-Oxathiolan-5-one Derivatives2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 20, p. 6129-6132Article in journal (Refereed)
    Abstract [en]

    Dynamic hemithioacetal systems were efficiently generated in organic solvents and subsequently allowed to react with a range of lipases. This resulted in direct, dynamic asymmetric transformation of the systems, leading to optically active 1,3-oxathiolan-5-one products. The tandem process identified lipase-catalyzed lactonization as a useful method for the resolution of optimal constituents with high chemo- and stereoselectivities.

  • 10.
    Sakulsombat, Morakot
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Zhang, Yan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dynamic systemic resolution2012In: Constitutional Dynamic Chemistry / [ed] Barboiu M., Springer Berlin/Heidelberg, 2012, Vol. 322, p. 55-86Chapter in book (Refereed)
    Abstract [en]

    Dynamic Systemic Resolution is a powerful technique for selecting optimal constituents from dynamic systems by applying selection pressures, either externally by addition of target entities, or internally within the system constraints. This concept is a subset of Constitutional Dynamic Chemistry, and the dynamic systems are generally based on reversible covalent interactions between a range of components where the systems are maintained under thermodynamic control. In the present chapter, the concept will be described in detail, and a range of examples will be given for both selection classes. For external pressure generation, target enzymes, in aqueous and/or organic solution, have been used to demonstrate the resolution processes. In a first example, a dynamic transthiolesterification system was generated in aqueous solution at neutral pH, and resolved by hydrolysis using serine hydrolases (cholinesterases). In organic solution, lipase-catalyzed acylation was chosen to demonstrate asymmetric resolution in different dynamic systems, generating chiral ester and amide structures. By use of such biocatalysts, the optimal constituents were selectively chosen and amplified from the dynamic systems in one-pot processes. In internal selection pressure resolution, self-transformation and crystallization-induced diastereomeric resolution have been successfully used to challenge dynamic systems. The technique was, for example, used to identify the best diastereomeric substrate from a large and varied dynamic system in a single resolution reaction.

  • 11.
    Vongvilai, Pornrapee
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Linder, Mats
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry (closed 20110630).
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Humble, Maria Svedendahl
    KTH, School of Biotechnology (BIO), Biochemistry.
    Berglund, Per
    KTH, School of Biotechnology (BIO), Biochemistry.
    Brinck, Tore
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry (closed 20110630).
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Racemase Activity of B. cepacia Lipase Leads to Dual-Function Asymmetric Dynamic Kinetic Resolution of alpha-Aminonitriles2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 29, p. 6592-6595Article in journal (Refereed)
    Abstract [en]

    Applaudable promiscuity: Racemase-type activity discovered for B. cepacia lipase with N-substituted α-aminonitriles is proposed to involve a C-C bond-breaking/forming mechanism in the hydrolase site of the enzyme, as supported by experimental data and calculations. This promiscuous activity in combination with the transacylation activity of the enzyme enabled the asymmetric synthesis of N-methyl α-aminonitrile amides in high yield (see scheme).

  • 12.
    Vongvilai, Pornrapee
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    In Situ Evaluation of Lipase Performances Through Dynamic Asymmetric Cyanohydrin ResolutionManuscript (preprint) (Other academic)
  • 13. Zhang, Yan
    et al.
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Hu, Lei
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Lipase-mediated dynamic systemic resolution based on single or double reversible reactions2012In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 244Article in journal (Other academic)
  • 14.
    Zhang, Yan
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Schaufelberger, Fredrik
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Liu, Chelsea
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Asymmetric Dynamic Kinetic Resolution for the Synthesis of 1,3-Oxathiolan-5-one DerivativesArticle in journal (Other academic)
    Abstract [en]

    Synthesis of 1,3-oxathiolan-5-one derivatives through dynamic kinetic resolution strategy has been illustrated, resulting in moderate to good enantioselectivities of the final products. In addition, the substrate scope and potential access to lamivudine (3TC) have also been explored.

  • 15.
    Zhang, Yan
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Schaufelberger, Fredrik
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Liu, Chelsea
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Asymmetric synthesis of 1,3-oxathiolan-5-one derivatives through dynamic covalent kinetic resolution2014In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 70, no 24, p. 3826-3831Article in journal (Refereed)
    Abstract [en]

    The asymmetric synthesis of 1,3-oxathiolan-5-one derivatives through an enzyme-catalyzed, dynamic covalent kinetic resolution strategy is presented. Dynamic hemithioacetal formation combined with intramolecular, lipase-catalyzed lactonization resulted in good conversions with moderate to good enantiomeric excess (ee) for the final products. The process was evaluated for different lipase preparations, solvents, bases, and reaction temperatures, where lipase B from Candida antarctica (CAL-B) proved most efficient. The substrate scope was furthermore explored for a range of aldehyde structures, together with the potential access to nucleoside analog inhibitor core structures.

  • 16.
    Zhang, Yan
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Asymmetric Synthesis of Substituted Thiolanes through Domino Thia-Michael-Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis2014In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 356, no 5, p. 987-992Article in journal (Refereed)
    Abstract [en]

    Dynamic systems based on consecutive thia-Michael and Henry reactions were generated and transformed using lipase-catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.

  • 17.
    Zhang, Yan
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Vongvilai, Pornrapee
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Sakulsombat, Morakot
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Biocatalyzed Dynamic Systemic Domino Thia-Michael--Henry Resolution to Substituted Asymmetric ThiolanesArticle in journal (Other academic)
    Abstract [en]

    Dynamic systems based on consecutive thia-Michael and Henry reactions were generated and transformed using lipase-catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.

1 - 17 of 17
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