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  • 1.
    Hu, Lei
    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.
    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.
    Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution2013In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 49, no 88, p. 10376-10378Article in journal (Refereed)
    Abstract [en]

    The anti-HIV nucleoside lamivudine was asymmetrically synthesized in only three steps via a novel surfactant-treated subtilisin Carlsberg-catalyzed dynamic kinetic resolution protocol. The enantiomer of lamivudine could also be accessed using the same protocol catalyzed by Candida antarctica lipase B.

  • 2.
    Hu, Lei
    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.
    Asymmetric Synthesis of Lamivudine and its Enantiomer: Mechanism of Chirality Control in Enzyme-Catalyzed 1,3-Oxathiolane Ring Closing ProcessesManuscript (preprint) (Other academic)
  • 3.
    Hu, Lei
    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.
    Gelation-Driven Dynamic Systemic Resolution: in situ Generation and Self-Selection of an OrganogelatorManuscript (preprint) (Other academic)
  • 4.
    Hu, Lei
    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.
    Lipase-catalyzed asymmetric synthesis of oxathiazinanones through dynamic covalent kinetic resolution2014In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 12, no 22, p. 3572-3575Article in journal (Refereed)
    Abstract [en]

    A domino addition-lactonization pathway has been applied to a dynamic covalent resolution protocol, leading to efficient oxathiazinanone formation as well as chiral discrimination. A new, double biocatalytic pathway has furthermore been proposed and evaluated where the initial product inhibition could be efficiently circumvented.

  • 5.
    Hu, Lei
    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.
    Lipase-Catalyzed Dynamic Kinetic Asymmetric Transformation to OxathiazinanonesArticle in journal (Other academic)
    Abstract [en]

    A domino addition-lactonization pathway has been applied to a dynamic covalent resolution protocol, leading to efficient oxathiazinanone formation as well as chiral discrimination. A new, double biocatalytic pathway has furthermore been proposed and evaluated where initial product inhibition could be efficiently circumvented.

  • 6.
    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.

  • 7.
    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.

  • 8.
    Zhang, Yan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Chemoenzymatic Resolution in Dynamic Systems: Screening, Classification and Asymmetric Synthesis2013Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This  thesis  is  divided  into  four  parts,  all  centered  around  Constitutional Dynamic  Chemistry  (CDC)  and  Dynamic  Kinetic  Resolution  (DKR)  using biocatalysts for selective transformations, and their applications in screening of bioactive compounds, organic synthesis, and enzyme classification.   

    In  part  one,  an  introduction  to  CDC  and  DKR  is  presented,  illustrating  the basic  concepts,  practical  considerations  and  potential  applications  of  such dynamic systems, thus providing the background information for the studies in the following chapters.  

    In part two, Dynamic Systemic Resolution (DSR), a concept based on CDC is exemplified.  With  enzyme-catalyzed  transformations  as  external  selection pressure,  optimal  structures  can  be  selected  and  amplified  from  the  system. This  concept  is  expanded  to  various  types  of  dynamic  systems  containing single, double cascade/parallel, and multiple reversible reactions. In addition, the  substrate  selectivity  and  catalytic  promiscuity  of  target  enzymes  are  also investigated.  

    In   part   three,   DKR   protocols   using   reversible   reactions   for   substrate racemizations  are  illustrated.  Biocatalysts  are  here  employed  for  asymmetric transformations,  resulting  in  efficient  synthetic  pathways  for  enantioenriched organic compounds.  

    Part  four  demonstrates  two  unique  applications  of  CDC:  one  resulting  in enzyme  classification  by  use  of  pattern  recognition  methodology;  the  other involving  enzyme  self-inhibition  through  in  situ  transformation  of  stealth inhibitors employing the catalytic activity of the target enzyme.

  • 9.
    Zhang, Yan
    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.
    Larsson, Rikard
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Albers, Antonia
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Simons, Adrian
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Tandem driven dynamic self-inhibition of acetylcholinesterase2010In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 46, no 44, p. 8457-8459Article in journal (Refereed)
    Abstract [en]

    A concept of tandem driven dynamic self-inhibition is demonstrated through dynamic inhibitors of acetylcholinesterase (AChE) using reversible transthiolesterification.

  • 10.
    Zhang, Yan
    et al.
    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.
    Double parallel dynamic resolution through lipase-catalyzed asymmetric transformation2013In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 49, no 18, p. 1805-1807Article in journal (Refereed)
    Abstract [en]

    Dynamic systems based on double parallel reactions have been generated and resolved in situ by secondary lipase-catalyzed asymmetric transformation, resulting in high chemo- and enantioselectivities.

  • 11.
    Zhang, Yan
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Jayawardena, Surangi
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Classification of Lipases Using Pattern Recognition through Transformation of Dynamic Hemithioacetal SystemsArticle in journal (Other academic)
    Abstract [en]

    A complex dynamic hemithioacetal system was generated for the evaluation of lipase reactivities. In combination with pattern recognition methodology, twelve different lipases were successfully classified into three distinct groups following their reaction selectivities and reactivities. A probe lipase was further categorized using the training matrix with predicted reactivity.

  • 12.
    Zhang, Yan
    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.
    Lipase-Catalyzed Dynamic Systemic Resolution from Reversible Reaction NetworksArticle in journal (Other academic)
    Abstract [en]

    A dynamic system based on a network of multiple reversible reactions has been established. The network was applied to a dynamic systemic resolution protocol based on two kinetically controlled lipase-catalyzed transformations, where two compounds were efficiently selected from a pool of potential products.

  • 13.
    Zhang, Yan
    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.
    Thiazolidinones Derived from Dynamic Systemic Resolution of Complex Reversible-Reaction Networks2014In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 12, p. 3288-3291Article in journal (Refereed)
    Abstract [en]

    A complex dynamic system based on a network of multiple reversible reactions has been established. The network was applied to a dynamic systemic resolution protocol based on kinetically controlled lipase-catalyzed transformations. This resulted in the formation of cyclized products, where two thiazolidinone compounds were efficiently produced from a range of potential transformations.

  • 14. 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)
  • 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 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.

  • 16.
    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.

  • 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.
    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.

  • 18.
    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.

  • 19.
    Zhang, Yang
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Zhang, Yan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Xie, Sheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Yan, Mingdi
    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-catalyzed kinetic resolution of 3-phenyloxazolidin-2-one derivatives: Cascade O- and N-alkoxycarbonylations2016In: Catalysis communications, ISSN 1566-7367, E-ISSN 1873-3905, Vol. 82, p. 11-15Article in journal (Refereed)
    Abstract [en]

    A lipase-catalyzed, cascade kinetic resolution protocol has been established for the synthesis of 3-phenyloxazolidin-2-one derivatives with up to excellent enantioselectivities (95% ee). Candida antarctica lipase B showed high catalytic activity and stereoselectivity in sequential O- and N-alkoxycarbonylation processes.

1 - 19 of 19
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  • ieee
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