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University of Helsinki Laboratory of Organic Chemistry
 

Laboratory of Organic Chemistry

Laboratory Info:

Contact Information:

Laboratory of Organic Chemistry
Department of Chemistry
University of Helsinki
P.O. Box 55
FI-00014 UNIVERSITY OF HELSINKI

Structural chemistry

Kuva

Project Leader:
Professor Ilkka Kilpeläinen

Members:
Jussi Helminen, MSc
Ashley Holding, MSc
Uula Hyväkkö, MSc
Niklas Johansson, MSc
Tia Kakko, MSc
Pirkko Karhunen, PhD
Alistair King, PhD
Tuomas Kulomaa, MSc
Annika Kyburz, MSc
Maarit Lahtinen, PhD
Valtteri Mäkelä, MSc
Arno Parviainen, MSc
Katja Sievänen, MSc


Recent Publications:

Kulomaa, T.P.S., Matikainen, J., Karhunen, P., Fiskari, J., Kilpeläinen, I. and Heikkilä, M.; Cellulose fatty acid esters as sustainable film materials – effect of side chain structure on barrier and mechanical properties, RSC Adv. (2015), http://dx.doi.org/10.1039/C5RA12671A

Parviainen, A., Wahlström, R. M., Liimatainen, U., Liitiä, T., Rovio, S., Helminen, J. K. J., Hyväkkö, U. T., King, A. W. T., Suurnäkki, A. and Kilpeläinen, I
Sustainability of cellulose dissolution and regeneration in 1,5-diazabicyclo[4.3.0]non-5-enium acetate: a batch simulation of the IONOCELL-F process, RSC Adv. (2015), Ahead of Print

Ruokonen, S.-K., Dusa, F., Lokajova, J., Kilpeläinen, I., King, A. W. T. and Wiedmer, S. K. Effect of ionic liquids on the interaction between liposomes and common wastewater pollutants investigated by capillary electrophoresis, J. Chromatogr. A (2015), Ahead of Print.  

Sievänen, K., Kavakka, J., Hirsilä, P., Vainio, P., Karisalmi, K., Fiskari, J. and Kilpeläinen, I. Cationic cellulose betainate for wastewater treatment, Cellulose (Dordrecht, Netherlands) 22 (2015), 1861-1872.

Sixta, H., Michud, A., Hauru, L., Asaadi, S., Ma, Y., King, A.W. T., Kilpeläinen, I. and Hummel, M.
Ionocell-F: a high-strength regenerated cellulose fibre, Nord. Pulp Paper Res. J. 30 (2015), 43-57.  

Mikkola, S.-K., Robcius, A., Lokajova, J., Holding, A.J., Lammerhofer, M., Kilpeläinen, I., Holopainen, J.M., King A.W.T. and Wiedmer, S.K.;
Impact of Amphiphilic Biomass-Dissolving Ionic Liquids on Biological Cells and Liposomes, Env. Sci. Technol. 49 (2015) 1870-1878.

Labafzadeh, S. R., Helminen ,K. J., Kilpeläinen, I. and King A. W. T.
Synthesis of Cellulose Methylcarbonate in Ionic Liquids using Dimethylcarbonate, ChemSusChem 8 (2015) 77-81
.
Labafzadeh, S.R., Vyavaharkar, K., Kavakka, J.S., King, A.W.T. and Kilpeläinen, I.
Amination and thiolation of chloroacetyl cellulose through reactive dissolutuin in N,N-dimethylformamide, Carbohydr. Polym. 116 (2015), 60-6.

Mikkola, S.-K., Robcius, A., Lokajova, J., Holding, A.J., Lammerhofer, M., Kilpeläinen, I., Holopainen, J.M., King A.W.T. and Wiedmer, S.K.;
Impact of Amphiphilic Biomass-Dissolving Ionic Liquids on Biological Cells and Liposomes, Env. Sci. Technol. 49 (2015) 1870-1878.

Parviainen, H., Parviainen, A., Virtanen, T., Kilpeläinen, I., Ahvenainen, P., Serimaa, R., Grönqvist, S., Maloney, T. and Maunu, S.L.
Dissolution enthalpies of cellulose in ionic liquids, Carbohydr. Polym. 113 (2014) 67-76.

King, A. W. T., Xie, H., Fiskari, J. and Kilpeläinen, I.
Reduction of biomass recalcitrance via ionic liquid pretreatments, Materials and Energy, 4 (2014) 95-125.

Sirviö, J. A., Anttila, A.-K., Pirttilä, A. M., Liimatainen, H., Kilpeläinen, I., Niinimäki, J. and Hormi, O.; Cationic wood cellulose films with high strength and bacterial anti-adhesive properties, Cellulose (2014), http://dx.doi.org/10.1007/s10570-014-0351-y

Labafzadeh, S. R., Kavakka, J. S., Vyavaharkar, K., Sievänen, K. and  Kilpeläinen, I.; Preparation of cellulose and pulp carbamates through a reactive dissolution approach, RSC Adv. 4 (2014) 22434-22441.

Holding, A. J., Heikkilä, M., Kilpeläinen, I. and King A.W.T.
Amphiphilic and Phase-Separable Ionic Liquids for Biomass Processing, ChemSusChem (2014) http://dx.doi.org/10.1002/cssc.201301261

Hyvakkö, U., King, A. W. T. and Kilpeläinen, I.
Extraction of wheat straw with aqueous tetra-​n-​butylphosphonium hydroxide, BioRes. 9 (2014) 1565-1577.

Labafzadeh, S. R., Vyavaharkar, K., Kavakka, J. S., King, A.W. T. and Kilpeläinen, I.
Amination and thiolation of chloroacetyl cellulose through reactive dissolution in N,​N-​dimethylformamide, Carbohydr. Polym. (2014) http://dx.doi.org/10.1016/j.carbpol.2014.03.077

Kalinowski, J., Räsänen, M., Heinonen, P., Kilpeläinen, I. and Gerber, R.B.; Isomerization and decomposition of Criegee intermediate in the ozonolysis of alkenes: dynamics using a multireference potential, Angew. Chem. (Int. ed.) 53 (2014) 265-8. http://dx.doi.org/10.1002/anie.201307286

Parviainen, A., King, A.W.T., Mutikainen, I., Hummel, M., Selg, C., Hauru, L.K.J, Sixta, H. and Kilpeläinen I.; Predicting Cellulose Solvating Capabilities of Acid Base Conjugate Ionic Liquids, Chem. Sis. Chem (2013), http://dx.doi.org/10.1002/cssc.201300143

Sakakibara, K., Granström, M., Kilpeläinen, I., Helaja, J., Heinilehto, S., Inoue, R., Kanaya, T., Hill, J. P., Nakatsubo, F., Tsujii, Y. and Katsuhiko, A.; Light-Harvesting Nanorods Based on Pheophorbide-Appending Cellulose, Biomacromol. (2013)
http://dx.doi.org/10.1021/bm400858v

Garcia, V., Valkama, H., Sliz, R., King, A. W. T., Myllylä, R., Kilpeläinen, I. and  Keiski, R. L.;Pervaporation recovery of [AMIM]Cl during wood dissolution; effect of [AMIM]Cl properties on the membrane performance, J. Membr. Sci. 444 (2013) 9-15.

Mäkelä, V., Karhunen, P., Siren, S., Heikkinen, S. and Kilpeläinen, I.; Automating the NMR analysis of base oils: Finding naphthene signals, Fuel (2013), http://dx.doi.org/10.1016/j.fuel.2013.04.020

Lahtinen, M., Viikari, L., Karhunen, P., Asikkala, J., Kruus, K. and I. Kilpeläinen, On the reactivity of the Melanocarpus albomyces laccase and formation of coniferyl alcohol dehydropolymer (DHP) in the presence of ionic liquid 1-allyl-3-methylimidazolium chloride, J. Mol. Catal. B: Enzym. 85-86 (2013) 169-177, http://pubs.acs.org/doi/10.1016/j.molcatb.2012.09.005

Leskinen, T., King, A.W.T., Kilpeläinen, I. and Argyropoulos D. S.; Fractionation of Lignocellulosic Materials Using Ionic Liquids: Part 2. Effect of Particle Size on the Mechanism of Fractionation, Ind. Eng. Chem. Res. 52 (2013) 3958-3966.

Hauru, L. K. J., Hummel, M., King, A. W. T., Kilpeläinen, I. and Sixta, H.; Role of Solvent Parameters in the Regeneration of Cellulose from the Ionic Liquid Solutions, Biomacromol. 13 (2012), 2896-2905 http://dx.doi.org/10.1021/bm300912y

Lahtinen, M., Viikari, L., Karhunen, P., Asikkala, J., Kruus, K. and I. Kilpeläinen, On the reactivity of the Melanocarpus albomyces laccase and formation of coniferyl alcohol dehydropolymer (DHP) in the presence of ionic liquid 1-allyl-3-methylimidazolium chloride, J. Mol. Catal. B: Enzym. (2012), http://pubs.acs.org/doi/10.1016/j.molcatb.2012.09.005

Tossavainen, H., Koskela, O., Jiang, P., Ylänne, J., Campbell, I.D., Kilpeläinen, I. and Permi, P.Model of a Six Immunoglobulin-Like Domain Fragment of Filamin A (16−21) Built Using Residual Dipolar Couplings, J. Am. Chem. Soc.134 (2012) 6660-6672.

King, A.W.T., Asikkala, J., Mutikainen, I., Järvi, P.K. and Kilpeläinen I.; Distillable Acid-Base Conjugate Ionic Liquids for Cellulose Dissolution and Processing, Angew. Chem. (Int. Ed.) 50 (2011) 6301-6305.

Havimo, M., Jalomäki, J., Granström, M., Rissanen, A., Iivanainen, T., Kemell, M., Heikkilä, M., Sipi, M. and Kilpeläinen, I.; Mechanical Strength and Water Resistance of Paperboard Coated with Long Chain Cellulose Esters, Packag. Technol. Sci. 24 249-258.

Zoia, L., King, A:W:T and Argyropoulos, D.; Molecular Weight Distribution and Linkages in Lignocellulosic Materials Derivatized from Ionic Liquid Media, J. Agric. & Food Chem. 59 (2011) 829-838.

Granström M., Kettunen, M, Jin, H., Kolehmainen, E., Kilpeläinen, I. and Ikkala, O.; Highly Water Repellent Aerogels Based on Cellulose Stearoyl Esters, Polym. Chem. 2 (2011) 1789-1796.

Mäkelä, A.V., Heikkilä, O., Kilpeläinen, I. and Heikkinen, S.; ImatraNMR: Novel Software for Batch Integration and Analysis of Quantitative NMR Spectra, J. Magn. Reson. 211 (2011) 186-194.

Leskinen, T., King, A. W. T., Kilpeläinen, I. and Argyropoulos, D. S.; Fractionation of Lignocellulosic Materials with Ionic Liquids. 1. Effect of Mechanical Treatment, Ind. Engin. Chem. Res. 50 (2011) 12349–12357, http://dx.doi.org/10.1021/ie200063x

Rauhala, T., King, A.W.T, Zuckerstatter, G., Suuronen and S. Sixta, H.; Effect of Autohydrolysis on The Lignin Structure And The Kinetics of Delignification of Birch Wood, Nordic Pulp & Paper Res. J. 26 (2011) 386-391.

Mäkelä, A.V., Kilpeläinen, I. and Heikkinen, S.
Quantitative 13C NMR Spectroscopy Using Refocused Constant-time INEPT, Q-INEPT-CT
J. Magn. Reson. 204 (2010) 124-130.

Koskela, H., Heikkilä, O., Kilpeläinen, I. and Heikkinen, S.
Quantitative Two-Dimensional HSQC Experiment for High Magnetic Field NMR Spectrometers
J. Magn. Reson. 202 (2010) 24-33.

Heikkinen, O.K., Ruskamo, S., Konarev, P.V., Svergun, D., Iivanainen, T., Heikkinen, S.M., Permi, P., Koskela, H., Kilpeläinen, I. and Ylänne, J.
Atomic Structures of Two Novel Immunoglobulin-like Domain Pairs in the Actin Cross-linking Protein Filamin
J. Biol. Chem. 284 (2009) 25450-25459.

King, A.W.T, Zoia, L., Filpponen, I., Olszewska, A., Xie, H., Kilpeläinen, I. and Argyropoulos, D.S.
In Situ Determination of Lignin Phenolics and Wood Solubility in Imidatzolium Chlorides Using 31P NMR
J. Agric. Food. Chem. (2009), http://dx.doi.org/10.1021/jf901095w

Heikkinen, O., Permi, P., Koskela, H., Carpén, O, Ylänne, J. and Kilpeläinen, I.
Solution Structure of the First Immunoglobulin Domain of Human Myotilin
J. Biomol. NMR 44 (2009) 107-112.

Heikkinen, O., Permi, P., Koskela, H., Ylänne, J. and Kilpeläinen, I.
1H, 13C and 15N Resonance Assignment of The Human Filamin A Tandem Immunoglobulin-like Domains 16-17 and 18-19
Biomol NMR Assign 3 (2009), 53-56.

Kavakka, J.S., Kilpeläinen, I. and Heikkinen, S.
General Chromatographic NMR Method in Liquid State for Synthetic Chemistry: Polyvinylpyrrolidone Assisted DOSY Experiments
Org. Lett. 11 (2009),1349-1352. http://dx.doi.org/10.1021/ol9001398 .

Granström, M., Olszewska, A., Mäkelä, V., Heikkinen, S. and Kilpeläinen, I.
A New Protection Group Strategy for Cellulose in an Ionic Liquid: Simultaneous Protection of Two sites to Yield 2,6-Di-O-substituted Mono- p -methoxytrityl Cellulose
Tetrahedron Lett. 50 (2009), 1744-1747. http://dx.doi.org/10.1016/j.tetlet.2009.01.144 .

Xie, H., Järvi, P., Karesoja, M., King, A., Kilpeläinen, I. and Argyropoulos, D.S.
Highly Compatible Wood Thermoplastic Composites from Lignocellulosic Material Modified in Ionic Liquids: Preparation and Thermal Properties
J. Appl. Polym. Sci, 111 (2009), 2468-2476.

King, A.W.T., Kilpeläinen, I. , Heikkinen, S., Järvi, P. and Argyropoulos, D.S.
Hydrophobic Interactions Determining Functionalized Lignocellulose Solubility in Dialkylimidazolium Chloride as Probed by 31 P NMR
Biomacromolecules 10 (2009),458-463. http://dx.doi.org/10.1021/bm8010159

Kavakka, J., Heikkinen, S., Kilpeläinen, I., Tkachenko, N.V. and Helaja, J.
Zn Pyro -pheophorbide a Fulleronicotine Dyad; Supramolecular Self Assembled Donor Acceptor System for Photoinduced Charge Separation
Chem. Comm. (2009), 758-760. http://dx.doi.org/10.1039/b817701e

Granström, M., Havimo, M., Heikkilä, M. and Kilpeläinen, I.
Synthesis, Characterisation and Application of Novel Self-Assembled Comb-Like Liquid Crystalline Biphenylcellulose as UV Absorber for Paper
J. Mater. Chem. 19 (2009), 639-644. http://dx.doi.org/ 10.10 39/b815600j

Granström, M., Majoinen, J., Kavakka, J., Heikkilä, M., Kemell, M. and Kilpeläinen, I .
Effect of Self-Assembly via p-Stacking to Morphology and Crystallinity on Tritylated Cellulose
Mater. Lett. 63 (2009), 473-476.

Parshintsev, J., Nurmi, J., Kilpeläinen, I. , Hartonen, K., Kulmala, M. and Riekkola, M.-L. Preparation of beta -Caryophyllene Oxidation Products and Their Determination in Ambient Aerosol Samples
Anal. Bioanal. Chem. 390 (2008) 913-919.

Granstöm, M., Kavakka, J., King, A., Majoinen, J., Mäkelä, V., Helaja, J., Hietala, S., Virtanen, T., Maunu, S.L., Argyropoulos, D.S. and Kilpeläinen I.
Tosylation and Acylation of Cellulose in 1-Allyl-3-methylimidazolium Chloride
Cellulose , 15 (2008) 481-488.

Kavakka, J.S., Heikkinen, S., Kilpeläinen, I. , Mattila, M., Lipsanen, H. and Helaja, J. Noncovalent Attachment of Pyro -Pheophorbide a to a Carbon Nanotube
Chem. Commun. (2007) 519-521.

Leppänen, V-M., Tossavainen, H., Permi, P., Lehtiö, L., Rönnholm, G., Goldman, A., Kilpeläinen, I. and Pihlajamaa , T.
Crystal Structure of the N-terminal NC4 Domain of Collagen IX, a Zinc Binding Member of the Laminin-Neurexin-Sex Hormone Binding Globulin (LNS) Domain Family
J. Biol. Chem. 282 (2007) 23219-23230.

Seppänen, S-K., Pasonen, H-L., Vauramo, J., Vahala, J., Toikka, M., Kilpeläinen, I., Setälä, H., Teeri, T.H., Timonen, S. and Pappinen, A.
Decomposition of the leaf litter and mycorrhiza forming ability of silver birch with a genetically modified lignin biosynthesis pathway
Appl. Soil Ecology 36 (2007) 100-106.

Xie, H., King, A., Kilpeläinen, I. , Granström, M. and Argyropoulos, D. S.
Thorough Chemical Modification of Wood-Based Lignocellulosic Materials in Ionic Liquids
Biomacromolecules 8 (2007) 3740-3748.

Kilpeläinen, I. , Xie, H., King, A., Granstöm, M., Heikkinen, S. and Argyropoulos, D.S. Dissolution of Wood in Ionic Liquids
J. Agric. Food Chem. 55 (2007) 9142-9148.

Koskela, H., Kilpeläinen, I. and Heikkinen, S.
CAGEBIRD: Improving the GBIRD Filter with a CPMG Sequence
J. Magn. Res . 170 (2004) 121-126.

Pihlajamaa, T., Lankinen, H., Ylöstalo, J., Valmu, L., Jäälinoja, J., Zaucke, F., Spitznagel, L., Gösling, S., Puustinen, A., Mörgelin, M., Peränen, J., Maurer, P., Ala-Kokko, L. and Kilpeläinen, I.
Characterization of Recombinant Amino-terminal NC4 Domain of Human Collagen IX
J. Biol. Chem. 279 (2004) 24265-2427.

Axenov, K.V., Kilpeläinen, I., Klinga, M., Leskelä, M. and Repo, T.
Titanium and Zirconium Benzyl Complexes Bearing Bulky Bis(amido)cyclodiphosph(III)azanes: Synthesis, Structure, Activation, and Ethene Polymerization Studies
Organometallics 25 ( 2006) 463-471.

Nakamura, F., Pudas, R., Heikkinen, O., Permi, P., Kilpeläinen, I., Munday, A.D., Hartwig, J.H., Stossel, T.P. and Ylänne, J.
The Structure of the GPIb-filamin A Complex
Blood 107 (2006) 1925-1932.

Pääkkönen, K. Tossavainen, H., Permi, P., Rakkolainen, H., Rauvala, H., Raulo, E., Kilpeläinen, I. and Günter, P.
Solution Structures of the First and Fourth TSR Domains of F-Spondin
PROTEINS: Stucture, Function, and Bioinformatics 64 (2006) 665-672.

Tossavainen, H., Pihlajamaa, T., Huttunen, T.K., Raulo, E., Rauvala, H., Permi, P. and Kilpeläinen, I.
The Layered Fold of the TSR Domain of P. falciparum TRAP Contains a Heparin Binding Site Protein Science (2006), 1760-1768.

Tossavainen, H., Permi, P. Purhonen, S.L., Sarvas, M., Kilpeläinen, I. , Seppälä, R.
NMR solution structure and characterization of substrate binding site of the PPIase domain of PrsA protein from Bacillus subtilis
FEBS Lett.
(2006) 1822-1826.

Koskela, H., Kilpeläinen, I. and Heikkinen, S.
Some Aspects of Quantitative 2D NMR
J. Magn. Res. 174 (2005) 237-244.

Koutaniemi S., Toikka, M.M. Karkonen, A., Mustonen M., Lundell, T., Simola, L.K., Kilpeläinen, I.A. and Teeri, T.H.
Characterization of Basic p -Coumaryl and Coniferyl Alcohol Oxidizing Peroxidases from a Lignin-forming Picea abies Suspension Culture
Plant Molecular Biology 58 (2005) 141-57.

Legrand, S., Luukinen, H., Isaksson, R., Kilpeläinen, I. , Lindström, M., Nicholls, I.A. and Unelius, C.R.
Synthesis, NMR Conformational Studies and Host-Guest Behaviour of New (+)-Tartaric Acid Derivatives
Tetrahedron Asymmetry 16 (2005) 635-640.

Raulo, E., Tumova, S., Pavlov, I., Pekkanen, M., Hienola, A., Klankki, E., Kalkkinen, N., Taira, T., Kilpelainen, I. and Rauvala, H.
The Two Thrombospondin Type I Repeat Domains of the Heparin-binding Growth-associated Molecule Bind to Heparin/Heparan Sulfate and Regulate Neurite Extension and Plasticity in Hippocampal Neurons
J. Biol. Chem . 280 (2005) 41576-41583.

Silvennoinen, L., Koivunen, P., Myllyharju, J., Kilpelainen, I. and Permi, P.
NMR Assignment of the N -terminal Domain a of the Glycoprotein Chaperone ERp57
Journal of Biomolecular NMR 33 (2005) 136.