Wood chemistry and biomass valorization technologies
TalTech priority area
Research classification (Frascati)
Head of the research group
Research group member
Doctoral students
Keyword
X-ray crystallography
structural biology
biomass valorization
enzymology
rational design of biocatalysts
biocatalysis
Overview
The group is involved in a variety of research anddevelopment activities related to the valorizationof plant biomass. The direction of research activities that focus on the biological routes to valorization of biomass deal with soil bacteria andtheir enzymes as well as the study of lignolyticenzymes secreted by fungi (i.e. Cerrena unicolor)when grown on mandarin pomace waste as thegrowth substrate. In addition to that, some of theresearch focuses on enzymes from extremophilicorganisms that are involved in the deconstruction of lignocellulosic biomass. In addition to theenzymological characterization of those enzymes,the laboratory uses X-ray crystallography andsmall angle X-ray scattering methods to studytheir structure-function relationships.The research group is also involved in researchand development activities that are focused onthe development of fractionation and analyticalchemistry technologies of lignocellulosic biomass and on developing novel functional materialsfrom plant-based biopolymers. In the past year,in collaboration with the Agricultural Universityof Georgia, another project started with fundingfrom the Estonian Environmental InvestmentCentre that focuses on the valorization of mandarin pomace wastes.
Important results
Pupart, H.; Jõul, P.; Bramanis, M. I.; Lukk, T. (2023). Characterization of the Ensemble of LigninRemodeling DyP-Type Peroxidases from Streptomyces coelicolor A3(2). Energies, 16 (3), 1557. DOI: 10.3390/en16031557.
Related projects
Related department
- Jõul, P., Ho, T. T., Kallavus, U., Konist, A., Leiman, K., Salm, O-S., Kulp, M., Koel, M., Lukk, T. Characterization of organosolv lignins and their application in the preparation of aerogels // Materials (2022) vol. 15, 8, art. 2861.
https://doi.org/10.3390/ma15082861 - Zovo, K., Pupart, h., Van Wieren, A., Gillilan, R. E., Lukk, T. Substitution of the Methionine Axial Ligand of the T1 copper for the fungal-like Phenylalanine Ligand (M298F) causes local structural perturbations that lead to thermal instability and reduced catalytic efficiency of the small Laccase from Streptomyces coelicolor A3(2) // ACS omega (2022) vol. 7, 7, p. 6184-6194.
https://doi.org/10.1021/acsomega.1c06668 - Cronan, J.E., Lukk, T. Advances in the structural biology, mechanism, and physiology of cyclopropane fatty acid modifications of bacterial membranes // Microbiology and Molecular Biology Reviews (2022) vol. 86, 2
https://doi.org/10.1128/mmbr.00013-22 - Usmani, Z., Kulp, M., Lukk, T. Bioremediation of lindane contaminated soil: Exploring the potential of Actinobacterial strains // Chemosphere (2021) vol. 278, art. 130468, 12 p. : ill.
https://doi.org/10.1016/j.chemosphere.2021.130468 - Usmani, Z., Sharma, M., Awasthi, A. K., Lukk, T., Tuohy, M. G., Gong, L., Nguyen-Tri, P., Goddard, A. D., Bill, R. M., Nayak, S. C., Gupta, V. K Lignocellulosic biorefineries : the current state of challenges and strategies for efficient commercialization // Renewable and sustainable energy reviews (2021) Vol. 148, art. 111258, 14 p. : ill.
https://doi.org/10.1016/j.rser.2021.111258 - Usmani, Z., Lukk, T., Mohanachandran, D. K. et al. Biosafe sustainable antimicrobial encapsulation and coatings for targeted treatment and infections prevention: Preparation for another pandemic // Current Research in Green and Sustainable Chemistry (2021) vol. 4, art. 100074.
https://doi.org/10.1016/j.crgsc.2021.100074 - Usmani, Z., Sharma, M., Gupta, P., Karpichev, Y., Gathergood, N., Bhat, Rajeev. Gupta, V.K. Ionic liquid based pretreatment of lignocellulosic biomass for enhanced bioconversion // Bioresource technology (2020) vol. 304, art. 123003, 13 p.
https://doi.org/10.1016/j.biortech.2020.123003 - Usmani, Z., Sharma, M., Awasthi, A. K., Sivakumar, N., Lukk, T. et al. Bioprocessing of waste biomass for sustainable product development and minimizing environmental impact // Bioresource technology (2021) vol. 322, art. 124548, 12 p. : ill.
https://doi.org/10.1016/j.biortech.2020.124548 - Sharma, M., Usmani, Z., Gupta, V.K., Bhat, R. Valorization of fruits and vegetable wastes and by-products to produce natural pigments // Critical Reviews in Biotechnology (2021) Vol. 41, Issue 4, p. 535-563 : ill.
https://doi.org/10.1080/07388551.2021.1873240 - Usmani, Z., Sharma, M., Karpichev, Y. et al. Advancement in valorization technologies to improve utilization of bio-based waste in bioeconomy context // Renewable and sustainable energy reviews (2020) vol. 131, art. 109965, 16 p. : ill.
https://doi.org/10.1016/j.rser.2020.109965 - Gupta, P., Kumar, V., Usmani, Z., Rani, R., Chandra, A., Gupta, V.K. Implications of plant growth promoting Klebsiella sp. CPSB4 and Enterobacter sp. CPSB49 in luxuriant growth of tomato plants under chromium stress // Chemosphere (2020) Vol. 240, Art. nr. 124944.
https://doi.org/10.1016/j.chemosphere.2019.124944 - Sharma, M., Sudheer, S., Usmani, Z. et al. Deciphering the omics of plant-microbe interaction: perspectives and new insights // Current genomics (2020) vol. 21, 5, p. 343-362.
https://doi.org/10.2174/1389202921999200515140420 - Sana, S.S., Li, H., Zhang, Z., Sharma, M., Usmani, Z., Hou, T., Netala, V.R., Wang, X., Gupta, V.K. Recent advances in essential oils-based metal nanoparticles : a review on recent developments and biopharmaceutical applications // Journal of Molecular Liquids (2021) Vol. 333, Art. nr. 115951.
https://doi.org/10.1016/j.molliq.2021.115951 - Usmani, Z., Minaxi S., Sudheer, S. et al. Engineered microbes for pigment production using waste biomass // Current genomics (2020) vol. 21, 2, p. 80-95.
https://doi.org/10.2174/1389202921999200330152007 - Dalidovich, T., Mishra, K.A., Shalima, T., Kudrjašova, M., Kananovich, D. G., Aav, R. Mechanochemical synthesis of amides with uronium-based coupling reagents : a method for hexa-amidation of biotin[6]uril // ACS sustainable chemistry & engineering (2020) vol. 8, 41, p. 15703−15715 : ill.
https://doi.org/10.1021/acssuschemeng.0c05558 - Saar-Reismaa, P., Brilla, C.A., Leiman, K., Kaljurand, M., Vaher, M., Kulp, M., Mazina-Šinkar, J. Use of a newly-developed portable capillary electrophoresis analyser to detect drugs of abuse in oral fluid: A case study // Talanta (2020) vol. 211, art. 120662, 9 p.
https://doi.org/10.1016/j.talanta.2019.120662 - Jõul, P., Vaher, M., Kuhtinskaja, M. Carbon aerogel-based solid-phase microextraction coating for the analysis of organophosphorus pesticides // Analytical methods (2021) vol. 13, 1, p. 69−76 : ill.
https://doi.org/10.1039/D0AY02002H - Koel, M., Kuhtinskaja, M., Vaher, M. Extraction of bioactive compounds from Catharanthus roseus and Vinca minor // Separation and purification technology (2020) vol. 252, 1, art. 117438 ; 5 p. : ill.
https://doi.org/10.1016/j.seppur.2020.117438 - Sudheer, S., Gangwar, P., Usmani, Z., Sharma, M., Sharma, V.K., Sana, S.S., Almeida, F., Dubey, N.K., Singh, D.P., Dilbaghi, N., Khayat Kashani, H.R., Gupta, V.K., Singh, B.N., Khayatkashani, M., Nabavi, S.. Shaping the gut microbiota by bioactive phytochemicals : an emerging approach for the prevention and treatment of human diseases // Biochimie (2022) Vol. 193, p. 38 - 63.
https://doi.org/10.1016/j.biochi.2021.10.010 - Suk, M., Haiß, A., Westphal, J., Kapitanov, I.V., Karpichev, Y., Gathergood, N. et al. Design rules for environmental biodegradability of phenylalanine alkyl ester linked ionic liquids // Green chemistry (2020) vol. 22, 14, p. 4498−4508.
https://doi.org/10.1039/D0GC00918K - Velihina, Y., Scattolin, T., Bondar, D. et al. Synthesis, in silico and in vitro evaluation of novel oxazolopyrimidines as promising anticancer agents // Helvetica chimica acta (2020) vol. 103, 12, art. e2000169, 14 p. : ill.
https://doi.org/10.1002/hlca.202000169 - Saar-Reismaa, P., Kotkas, K., Rosenberg, V., Kulp, M., Kuhtinskaja, M., Vaher, M. Analysis of total phenols, sugars, and mineral elements in colored tubers of solanum tuberosum l. // Foods (2020) vol. 9, 12, art. 1862.
https://doi.org/10.3390/foods9121862 - Saar-Reismaa, P., Koel, M., Tarto, R., Vaher, M. Extraction of bioactive compounds from Dipsacus fullonum leaves using deep eutectic solvents // Journal of chromatography A (2022) vol. 1677, art. 463330.
https://doi.org/10.1016/j.chroma.2022.463330 - Pandya, S., Kapitanov, I., Usmani, Z., Gathergood, N., Karpichev, Y. et al. An example of green surfactant systems based on inherently biodegradable IL-derived amphiphilic oximes // Journal of molecular liquids (2020) vol. 305, 1, art. 112857.
https://doi.org/10.1016/j.molliq.2020.112857 - Banjare, M. K., Kamalakanta, B., Banjare, R. K., Pandey, S., Ghosh, K. K., Karpichev, Y. Molecular interactions between novel synthesized biodegradable ionic liquids with antidepressant drug // Chemical Thermodynamics and Thermal Analysis (2021) Vol. 3-4, art. 100012, 12 p.
https://doi.org/10.1016/j.ctta.2021.100012 - Koel, M., Kaljurand, M. Editorial overview : a closer look on green developments in analytical chemistry: green analytical chemistry is going mainstream // Current Opinion in Green and Sustainable Chemistry (2021) vol. 31, Art. 100541.
https://doi.org/10.1016/j.cogsc.2021.100541 - Dixit, M., Gupta, G.K., Usmani, Z., Sharma, M., Shukla, P. Enhanced bioremediation of pulp effluents through improved enzymatic treatment strategies : a greener approach // Renewable and Sustainable Energy Reviews (2021) Vol. 152, Art. 111664.
https://doi.org/10.1016/j.rser.2021.111664 - Trubitsõn, D., Martõnova, J., Kudrjašova, M., Erkman, K., Järving, I., Kanger T. Enantioselective organocatalytic Michael addition to unsaturated indolyl ketones // Organic letters (2021) vol. 23, 5, p. 1820-1824.
https://doi.org/10.1021/acs.orglett.1c00222 - Fujinami, D., Garcia de Gonzalo, C. V., Biswas, S., Hao, Y., Wang, H., Garg, N., Lukk, T., Nair, S. K., Donk, W. A. van der Structural and mechanistic investigations of protein S-glycosyltransferases // Cell Chemical Biology (2021) vol. 18, 12, p. 1740-1749.
https://doi.org/10.1016/j.chembiol.2021.06.009 - Usmani, Z., Sharma, M., Lukk, T., Karpichev, Y. et al Developments in enzyme and microalgae based biotechniques to remediate micropollutants from aqueous systems - a review // Critical reviews in environmental science and technology (2022) vol. 52, 10, p. 1684-1729.
https://doi.org/10.1080/10643389.2020.1862551 - Kuhtinskaja, M., Bragina, O., Kulp, M., Vaher, M. Anticancer Effect of the Iridoid Glycoside Fraction from Dipsacus fullonum L. Leaves // Natural product communications (2020) vol. 15, 9, p. 1-6.
https://doi.org/10.1177/1934578X20951417 - Kaljurand, M., Saar-Reismaa, P., Vaher, M., Gorbatšova, J., Mazina-Šinkar, J. Capillary electrophoresis as a monitoring tool for flow composition determination // Molecules (2021) vol. 26, 16, art. 4918, 12 p. : ill.
https://doi.org/10.3390/molecules26164918 - Jurjeva, J., Koel, M. Implementing greening into design in analytical chemistry // Talanta open (2022) vol. 6, art. 100136, 7 p.
https://doi.org/10.1016/j.talo.2022.100136 - Pandya, S. J., Kapitanov, I. V., Borovkov, V., Ghosh, K. K., Karpichev, Y. et al. Mixed oxime-functionalized IL/16-s-16 Gemini surfactants system: physicochemical study and structural transitions in the presence of promethazine as a potential chiral pollutant // Chemosensors (2022) vol. 10, 2, art. 46.
https://doi.org/10.3390/chemosensors10020046 - Saar-Reismaa, P., Bragina, O., Kuhtinskaja, M., Reile, I., Laanet, P.-R., Kulp, M., Vaher, M. Extraction and fractionation of bioactives from Dipsacus fullonum L. leaves and evaluation of their anti-borrelia activity // Pharmaceuticals (2022) vol. 15, 1, 12 p. : ill.
https://doi.org/10.3390/ph15010087 - Erkhova, L.V., Presniakov, I.A., Afanasov, M.I., Danilson, M., Koel, M. et al. Ferrocene introduced into 5-methylresorcinol-based organic aerogels // Polymers (2020) vol. 12, 7, art. 1582 ; 12 p. : ill.
https://doi.org/10.3390/polym12071582 - Laanet, P.-R., Vaher, M., Saar-Reismaa, P. Micellar electrokinetic chromatography method for the analysis of synthetic and phytocannabinoids // Journal of chromatography A (2022) vol. 1673, art. 463080.
https://doi.org/10.1016/j.chroma.2022.463080 - Parve, J., Kudryašova, M., Shalima, T., Villo, L., Liblikas, I., Reile, I., Pehk, T., Gathergood, N., Aav, R., Vares, L., Parve, O. Scalable lipase-catalyzed synthesis of (R)-4-(Acyloxy)pentanoic acids from racemic γ-valerolactone // ACS sustainable chemistry & engineering (2021) vol. 9, 4, p. 1494−1499.
https://doi.org/10.1021/acssuschemeng.0c07918 - Duvanova, E., Krasnou, I., Krumme, A., Mikli, V., Rozantsev, G. M., Radio, S.,Karpichev, Y. Development of Functional Composite Cu(II)-Polyoxometalate/PLA with Antimicrobial Properties // Molecules (2022) vol. 27, 8, art. 2510.
https://doi.org/10.3390/molecules27082510 - Bondar, D., Kapitanov, I. V., Pulkrabkova, L., Soukup, O., Jun, D., Botelho, F. D., Franca, T. C. C., Kuca, K., Karpichev, Y. N-substituted arylhydroxamic acids as acetylcholinesterase reactivators // Chemico-Biological Interactions (2022) vol. 365, art. 110078, 13 p. : ill.
https://doi.org/10.1016/j.cbi.2022.110078 - Ružicka, M., Kaljurand, M., Gorbatšova, J., Vaher, M., Mazina-Šinkar, J. Portable fully automated oral fluid extraction device for illegal drugs // Talanta (2022) vol. 243, art. 123389.
https://doi.org/10.1016/j.talanta.2022.123389 - Trybrat, O. O., Yesypenko, O. A., Shishkina, S. V., Rusanov, E. B., Karpichev, Y., Kalchenko, V. I. 25-Propyloxy-26,27-dibenzoyloxy-calix[4]arene as precursor for the synthesis of inherently chiral calixarenes // European Journal of Organic Chemistry (2021) Vol. 2021, 28, p. 3912-3919.
https://doi.org//10.1002/ejoc.202100624 - Bolkvadze, V., Bondar, D., Vaher, M., Halling, E., Gorbatsova, J., Mazina-Šinkar, J. The influence of organic solvents on phenylethylamines in capillary zone electrophoresis // Journal of chromatography A (2022) vol. 1675, art. 463169, 9 p. : ill.
https://doi.org/10.1016/j.chroma.2022.463169 - Lees, H., Jõul, P., Siilak, K., Vaher, M. Separation of perfluoroalkyl substances by using nonaqueous capillary electrophoresis with conductivity detection // Separation science plus (2020) vol. 3, 7, p. 313-320.
https://doi.org/10.1002/sscp.202000016 - Srivastava, S., Sharma, M., Usmani, Z. et al. Plant cell wall degrading enzymes in biomass bioprocessing to biorefineries: a review. Chapter 21 // Recent developments in bioenergy research. [S.l.] : Elsevier, 2020. p. 415-432.
https://doi.org/10.1016/B978-0-12-819597-0.00022-2 - Prits, A.-V., Nerut, J., Kasuk, H., Koel, M., Sepp, S., Valk, P., Aruväli, J., Koppel, M., Mikli, V., Volobujeva, O., Lust, E. Carbon aerogel platinum-praseodymium oxide nanocatalyst for methanol oxidation in 0.5 M sulfuric acid : (digital presentation) // ECS transactions (2022) vol. 108, 7, art. 79.
https://doi.org/10.1149/10807.0079ecst - Usmani, Z., Sharma, M., Karpichev, Y., Gathergood, N. et al. Pretreatment of plant feedstocks and agrofood waste using ionic liquids // Recent developments in bioenergy research. [S.l.] : Elsevier, 2020. p. 393-413.
https://doi.org/10.1016/B978-0-12-819597-0.00021-0 - Silenko, O., Cherenok, S., Karpichev, Y. Thiacalix[4]arene phosphoric acids. Synthesis, structure, and inhibition of glutathione S-transferases // Phosphorus, sulfur, and silicon and the related elements (2022) vol. 197, 5-6, p. 538-541.
https://doi.org/10.1080/10426507.2021.2011877 - Jurjeva, J., Koel, M. The chemometric approach to identification of residual oil contamination at former primitive asphalt pavement plants // Oil shale (2019) vol. 36, 3, p. 410-430 : ill.
http://www.kirj.ee/32501/?tpl=1061&c_tpl=1064 https://doi.org/10.3176/oil.2019.3.04 - Ernits, K, Eek, P., Lukk, T., Visnapuu, T., Alamäe, T. Author correction: First crystal structure of an endo-levanase – the BT1760 from a human gut commensal Bacteroides thetaiotaomicron (Scientific Reports, (2019), 9, 1, (8443), 10.1038/s41598-019-44785-0) // Scientific reports (2019) vol. 9, 1, art. 17512, 1 p..
https://doi.org/10.1038/s41598-019-54274-z - Ernits, K., Eek, P., Lukk, T. et al. First crystal structure of an endo-levanase - the BT1760 from a human gut commensal Bacteroides thetaiotaomicron // Scientific reports (2019) vol. 9, 1, art. 8443, 13 p. : ill.
https://doi.org/10.1038/s41598-019-44785-0 - Kumar, A., Usmani, Z., Ahirwal, J., Tripti, Rani, P. Phytomanagement of chromium contaminated brown fields // Phytomanagement of polluted sites : Market opportunities in sustainable phytoremediation. Amsterdam : Elsevier, 2019. p. 447-469.
https://doi.org/10.1016/B978-0-12-813912-7.00018-1 - Usmani, Z., Kumar, A., Tripti et al. Scope for Applying Transgenic Plant Technology for Remediation and Fortification of Selenium // Transgenic plant technology for remediation of toxic metals and metalloids. London : Academic Press, 2018. p. 429-461 : ill.
http://doi.org/10.1016/B978-0-12-814389-6.00020-1 - Gabdrakhmanov, D. R., Samarkina, D. A., Krylova, E. S., Kapitanov, I. V., Karpichev, Y. et al. Supramolecular systems based on novel amphiphiles and a polymer : aggregation and selective solubilization // Journal of surfactants and detergents (2019) vol. 22, 4, p. 865-874 : ill.
https://doi.org/10.1002/jsde.12257 - Lees, H., Zapata, F., Vaher, M., García-Ruiz, C. Study of the adhesion of explosive residues to the finger and transfer to clothing and luggage // Science & Justice (2018) vol. 58, 6, p. 415-424.
https://doi.org/10.1016/j.scijus.2018.07.002 - Lees, H., Zapata, F., Vaher, M., García-Ruiz, C. Simple multispectral imaging approach for determining the transfer of explosive residues in consecutive fingerprints // Talanta (2018) vol. 184, p. 437-445 : ill.
https://doi.org/10.1016/j.talanta.2018.02.079 - Trubitsõn, D., Žari, S., Kaabel, S., Kudrjashova, M., Kriis, K., Järving, I., Pehk, T., Kanger, T. Asymmetric organocatalytic cascade synthesis of tetrahydrofuranyl spirooxindoles // Synthesis (2018) vol. 50, 2, p. 314-322 : ill.
https://doi.org/10.1055/s-0036-1590918 - Savest, N., Plamus, T., Kütt, K., Kallavus, U., Viirsalu, M., Tarasova, E.,Vassiljeva, V., Krasnou, I., Krumme, A. Electrospun conductive mats from PANi-ionic liquid blends // Journal of electrostatics (2018) vol. 96, p. 40-44.
https://doi.org/10.1016/j.elstat.2018.09.007 - Söderström, M., Östin, A., Vaher, M., Jõul, P., Lees, H., Kaljurand, M. et al. Chemical analysis of dumped chemical warfare agents during the MODUM project // Towards the monitoring of dumped munitions threat (MODUM) : a study of chemical munitions dumpsites in the Baltic Sea. Dordrecht : Springer, 2018. p. 71-103. (NATO science for peace and security series. C, Environmental security).
https://doi.org/10.1007/978-94-024-1153-9_4 - Aid, T., Koel, M., Lopp, M., Vaher, M. Metal-catalyzed degradation of cellulose in ionic liquid media // Inorganics (2018) vol. 6, 3, art. 78, 11 p. : ill.
https://doi.org/10.3390/inorganics6030078 - Jõul, P., Vaher, M., Kuhtinskaja, M. Evaluation of carbon aerogel-based solid-phase extraction sorbent for the analysis of sulfur mustard degradation products in environmental water samples // Chemosphere (2018) Vol. 198, p. 460-468.
https://doi.org/10.1016/j.chemosphere.2018.01.157 - Ojangu, E.-L., Ilau, B., Tanner, K., Talts, K., Ihoma, E., Dolja, V. V., Paves, H., Truve, E. Class XI myosins contribute to auxin response and senescence-induced cell death in Arabidopsis // Frontiers in plant science (2018) vol. 9, art. 1570, 21 p. : ill.
https://doi.org/10.3389/fpls.2018.01570 - Bolobajev, J., Kask, M., Kreek, K., Kulp, M., Koel, M., Goi, A. Metal-doped organic aerogels for photocatalytic degradation of trimethoprim // Chemical engineering journal (2019) vol. 357, p. 120-128 : ill.
https://doi.org/10.1016/j.cej.2018.09.127 Tehnikaülikooli teadlaste meetod aitab puhastada reovett antibiootikumijääkidest https://keskkonnatehnika.ee/reovee-puhastamine-kasutades-aerogeele/ - Saar-Reismaa, P., Tretjakova, A., Mazina-Šinkar, J., Vaher, M., Kaljurand, M., Kulp, M. Rapid and sensitive capillary electrophoresis method for the analysis of Ecstasy in an oral fluid // Talanta (2019) vol. 197, p. 390-396 : ill.
https://doi.org/10.1016/j.talanta.2019.01.029 - Gupta, P., Kumar, V., Usmani, Z., Rani, R., Chandra, A., Gupta, V.K. A comparative evaluation towards the potential of Klebsiella sp. and Enterobacter sp. in plant growth promotion, oxidative stress tolerance and chromium uptake in Helianthus annuus (L.) // Journal of hazardous materials (2019) vol. 377, 7 p. : ill.
https://doi.org/10.1016/j.jhazmat.2019.05.054 - Kusumahastuti, D.K.A., Sihtmäe, M., Kapitanov, I., Karpichev, Y., Gathergood, N., Kahru, A. Toxicity profiling of 24 l-phenylalanine derived ionic liquids based on pyridinium, imidazolium and cholinium cations and varying alkyl chains using rapid screening Vibrio fischeri bioassay // Ecotoxicology and environmental safety (2019) vol. 172, p. 556-565 : ill.
https://doi.org/10.1016/j.ecoenv.2018.12.076 - Saar-Reismaa, P., Erme, E., Vaher, M., Kulp, M., Kaljurand, M., Mazina-Šinkar, J. In situ determination of illegal drugs in oral fluid by portable capillary electrophoresis with deep UV excited fluorescence detection // Analytical chemistry (2018) vol. 90, 10, p. 6253-6258 : ill.
https://doi.org/10.1021/acs.analchem.8b00911 - Kapitanov, I., Jordan, A.; Karpichev, Y., Gathergood, N. et al. Synthesis, self-assembly, bacterial and fungal toxicity, and preliminary biodegradation studies of a series of l-phenylalanine-derived surface-active ionic liquids // Green chemistry (2019) vol. 21, 7, p. 1777–1794 : ill.
https://doi.org/10.1039/c9gc00030e