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17 results on '"Långvik, Otto"'

4. Chemoselective heterogeneous iridium catalyzed hydrogenation of cinnamalaniline

Author

Savela, Risto, primary, Shcherban, Nataliya D., additional, Melander, Marko M., additional, Bezverkhyy, Igor, additional, Simakova, Irina L., additional, Långvik, Otto, additional, Kholkina, Ekaterina, additional, Schindler, Tamara, additional, Krauβ, Annabelle, additional, Honkala, Karoliina, additional, Murzin, Dmitry Yu., additional, and Leino, Reko, additional

Published
2021
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15. Cholesteryl Phosphocholine– A Study on ItsInteractions with Ceramides and Other Membrane Lipids.

Author

Lönnfors, Max, Långvik, Otto, Björkbom, Anders, and Slotte, J.Peter

Subjects
*CHOLESTERYL ester transfer protein, *CERAMIDES, *MEMBRANE lipids, *CHEMICAL synthesis, *MOLECULAR structure, *CHEMICAL models
Abstract

We prepared cholesteryl phosphocholine (CholPC) by chemicalsynthesisand studied its interactions with small (ceramide and cholesterol)and large headgroup (sphingomyelin (SM) and phosphatidylcholine) colipidsin bilayer membranes. We established that CholPC could form bilayers(giant uni- and multilamellar vesicles, as well as extruded largeunilamellar vesicles) with both ceramides and cholesterol (initialmolar ratio 1:1). The extruded bilayers appeared to be fluid, althoughhighly ordered, even when the ceramide had an N-linkedpalmitoyl acyl chain. In binary systems containing CholPC and eitherpalmitoyl SM or 1,2-dipalmitoyl-sn-glycero-3-phospholine,CholPC markedly destabilized the gel phase of the respective largeheadgroup lipid. In 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine(POPC) bilayers, CholPC was much less efficient than cholesterol inordering the acyl chains. In complex bilayers containing POPC andcholesterol or palmitoyl ceramide, CholPC appeared to prefer interactingwith the small headgroup lipids over POPC. When the degree of orderin CholPC/PCer bilayers was compared to Chol/PSM bilayers, CholPC/PCerbilayers were more disordered (based on DPH anisotropy). This findingmay result from different headgroup orientation and dynamics in CholPCand PSM. Our results overall can be understood if one takes into accountthe molecular shape of CholPC (large polar headgroup and modest sizehydrophobic part) when interpreting molecular interactions betweensmall and large headgroup colipids. The results are also consistentwith the proposed umbrella model” for explaining cholesterol/colipidinteractions. [ABSTRACT FROM AUTHOR]

Published
2013
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16. One-pot synthesis of (R)-2-acetoxy-1-indanone from 1,2-indanedione combining metal catalyzed hydrogenation and chemoenzymatic dynamic kinetic resolutionElectronic supplementary information (ESI) available: 1H-NMR spectra for (R)-3, 6and 7, DFT calculations results, chiral GC chromatograms and Ru catalyst characterization (HR-TEM, TPR, XPS). See DOI: 10.1039/c4cy01099j

Author

Långvik, Otto, Sandberg, Thomas, Wärnå, Johan, Murzin, Dmitry Yu., and Leino, Reko

Abstract

Combination of the regioselective hydrogenation of the prochiral diketone 1,2-indanedione with chemoenzymatic dynamic kinetic resolution of the resulting rac-2-hydroxy-1-indanone was investigated. A new simple to operate, one-pot reaction sequence provides the valuable building block (R)-2-acetoxy-1-indanone in moderate enantiopurity (86–92% ee) and a competitive isolated yield (39%) compared with a traditional isolated batch reaction approach.

Published
2014
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17. Dynamic Kinetic Resolution of rac‐2‐Hydroxy‐1‐indanone by using a Heterogeneous Ru(OH)3/Al2O3Racemization Catalyst and Lipase

Author

Långvik, Otto, Saloranta, Tiina, Kirilin, Alexey, Liljeblad, Arto, Mäki‐Arvela, Päivi, Kanerva, Liisa T., Murzin, Dmitry Yu., and Leino, Reko

Abstract

Kinetic resolution and dynamic kinetic resolution, in particular, provide practical tools for synthesis of enantiomerically pure compounds. In the present work, the resolution of rac‐2‐hydroxy‐1‐indanone and racemization of (S)‐2‐hydroxy‐1‐indanone were investigated. Immobilized lipase AK (Pseudomonas fluorescens) was found as the best enzyme catalyst for kinetic resolution and ruthenium supported on Al2O3as a potential heterogeneous catalyst for racemization of the starting material. By combining the two reactions, a simple dynamic kinetic resolution of rac‐2‐hydroxy‐1‐indanone producing (R)‐1‐oxo‐indan‐2‐yl butanoate was developed. Under optimal conditions, the product was obtained in 92 % eeat approximately 90 % conversion.

Published
2010
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