| 1. |
- Angelin, Marcus, et al.
(författare)
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Dynamic combinatorial resolution
- 2009
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Ingår i: Dynamic Combinatorial Chemistry. - Hoboken, NJ, USA : John Wiley & Sons. - 9780470096031 ; , s. 169-200
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Bokkapitel (refereegranskat)
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| 2. |
- Caraballo, Rémi, et al.
(författare)
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Phosphine-Mediated Disulfide Metathesis in Aqueous Media
- 2010
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Ingår i: Chemical Communications. - : Royal Society of Chemistry (RSC). - 1359-7345 .- 1364-548X. ; 46:44, s. 8469-8471
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Tidskriftsartikel (refereegranskat)abstract
- 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.
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| 3. |
- Caraballo, Rémi, et al.
(författare)
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Towards Dynamic Drug Design : Identification and Optimization of β-Galactosidase Inhibitors from a Dynamic Hemithioacetal System
- 2010
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Ingår i: ChemBioChem. - : Wiley. - 1439-4227 .- 1439-7633. ; 11:11, s. 1600-1606
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Tidskriftsartikel (refereegranskat)abstract
- 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.
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| 4. |
- Sakulsombat, Morakot, et al.
(författare)
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A Dynamic Multicomponent Approach for One-Pot Synthesis of 3-Thioisoindolinones
- 2013
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Ingår i: Israel Journal of Chemistry. - : Wiley. - 0021-2148 .- 1869-5868. ; 53:1-2, s. 127-132
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Tidskriftsartikel (refereegranskat)abstract
- 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.
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| 5. |
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| 6. |
- Sakulsombat, Morakot, et al.
(författare)
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Dynamic systemic resolution
- 2012
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Ingår i: Constitutional Dynamic Chemistry. - Berlin, Heidelberg : Springer Berlin/Heidelberg. - 9783642283437 ; , s. 55-86
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Bokkapitel (refereegranskat)abstract
- 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.
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| 7. |
- Sakulsombat, Morakot, 1978-
(författare)
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Dynamic Systems: Evaluation, Screening and Synthetic Application
- 2011
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Doktorsavhandling (övrigt vetenskapligt/konstnärligt)abstract
- 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.
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| 8. |
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| 9. |
- Sakulsombat, Morakot, et al.
(författare)
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In Situ Evaluation of Lipase Performances Through Dynamic Asymmetric Cyanohydrin Resolution
- 2011
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Ingår i: Organic and biomolecular chemistry. - : Royal Society of Chemistry (RSC). - 1477-0520 .- 1477-0539. ; 9:4, s. 1112-1117
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Tidskriftsartikel (refereegranskat)abstract
- 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.
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| 10. |
- Sakulsombat, Morakot, et al.
(författare)
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Tandem reversible addition-intramolecular lactonization for the synthesis of 3-functionalized phthalides
- 2010
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Ingår i: Tetrahedron Letters. - : Elsevier BV. - 0040-4039 .- 1359-8562. ; 51:1, s. 75-78
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Tidskriftsartikel (refereegranskat)abstract
- 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.
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