TY - JOUR T1 - The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study AU - Matin, Mohammed Mahbubul AU - Islam, Farzana AU - Rahman, Md. Rezaur PY - 2021 DA - June DO - 10.33435/tcandtc.914768 JF - Turkish Computational and Theoretical Chemistry JO - Turkish Comp Theo Chem (TC&TC) PB - Koray SAYIN WT - DergiPark SN - 2587-1722 SP - 39 EP - 50 VL - 5 IS - 1 LA - en AB - Carbohydrate fatty acid (CFA) esters especially rhamnopyranoside esters having both the hydrophilic and lipophilic nature showed broader applications including anticancer activities. It was reported that appropriate conformation is needed for better activities and conformational distortion reduced antimicrobial functionality. In this context, two different esters series of benzyl α-L-rhamnopyranosides, one with 2,3-O-acetonide group and the other one without acetonide group, were subjected for the density functional theory (DFT) optimization. The optimized structures with 2,3-O-acetonide rhamnopyranoside clearly showed distortion from the regular 1C4 chair conformation while rhamnopyranoside esters without 2,3-O-acetonide functionality exhibited almost regular 1C4 chair conformation. Also, the number and position of acyl group(s) present in the benzyl rhamnopyranoside imposes a small effect on their pyranose chair conformation. Thermodynamic properties including frontier molecular orbitals (FMO) and molecular electrostatic potential (MEP) of both the series of rhamnopyranosides are also discussed which indicated that 4-O-acyl rhamnopyranosides are more reactive than the 3-O-acyl analogues. KW - Conformational study KW - DFT optimization KW - MEP KW - Rhamnopyranoside KW - Sugar esters (SEs) KW - Thermodynamic properties CR - R. Hevey, Strategies for the development of glycomimetic drug candidates. Pharmaceuticals 12(2) (2019) 55. https://doi.org/10.3390/ph12020055 CR - H.M. Ei-Laithy, O. Shoukry, L.G.Mahran, Novel sugar esters proniosomes for transdermal delivery of vinpocetine: Preclinical and clinical studies. European Journal of Pharmaceutics and Biopharmaceutics 77 (2011) 43-55. https://doi.org/10.1016/j.ejpb.2010.10.011 CR - D.D. Dhavale, M.M. Matin, Selective sulfonylation of 4-C-hyroxymethyl--L-threo-pento-1,4-furanose: Synthesis of bicyclic diazasugars. Tetrahedron 60(19) (2004) 4275-4281. https://doi.org/10.1016/j.tet.2004.03.034 CR - D.D. Dhavale, M.M. Matin, T. Sharma, S.G. Sabharwal, Synthesis and evaluation of glycosidase inhibitory activity of octahydro-2H-pyrido[1,2-a]pyrimidine and octahydro-imidazo[1,2-a]pyridine bicyclic diazasugars. Bioorganic & Medicinal Chemistry 12 (2004) 4039-4044. https://doi.org/10.1016/j.bmc.2004.05.030 CR - A.M. Gumel, M.S.M. Annuar, T. Heidelberg, Y. Chisti, Lipase mediated synthesis of sugar fatty acid esters. Process Biochemistry 46 (2011) 2079-90. https://doi.org/10.1016/j.procbio.2011.07.021 CR - M.M. Matin, P. Chakraborty, M.S. Alam, M.M. Islam, U. Hanee, Novel mannopyranoside esters as sterol 14α-demethylase inhibitors: Synthesis, PASS predication, molecular docking, and pharmacokinetic studies. Carbohydrate Research 496 (2020) 108130. https://doi.org/10.1016/j.carres.2020.108130 CR - Y.L. Teng, S.G. Stewart, Y.W. Hai, X. Li, M.G. Banwell, P. Lan, Sucrose fatty acid esters: Synthesis, emulsifying capacities, biological activities and structure-property profiles. Critical Reviews in Food Science and Nutrition 2020. https://doi.org/10.1080/10408398.2020.1798346 CR - M.M. Matin, S.C. Bhattacharjee, P. Chakraborty, M.S. Alam, Synthesis, PASS predication, in vitro antimicrobial evaluation and pharmacokinetic study of novel n-octyl glucopyranoside esters. Carbohydrate Research 485 (2019) 107812. https://doi.org/10.1016/j.carres.2019.107812 CR - M.M. Matin, M.M.H. Bhuiyan, A.K.M.S. Azad, M.H.O. Rashid, Synthesis of 6-O-stearoyl-1,2-O-isopropylidene-α-D-gluco-furanose derivatives for antimicrobial evaluation. Journal of Physical Science 26(1) (2015) 1-12. CR - D.R. Perinelli, S. Lucarini, L. Fagioli, R. Campana, D. Vllasaliu, A. Duranti, L. Casettari, Lactose oleate as new biocompatible surfactant for pharmaceutical applications. European Journal of Pharmaceutics and Biopharmaceutics 124 (2018) 55-62. https://doi.org/10.1016/j.ejpb.2017.12.008 CR - A.V. Demchenko, Stereoselective chemical 1,2-cis O-glycosylation: From ‘Sugar Ray’ to modern techniques of the 21st century. Synlett (2003) 1225-1240. https://doi.org/10.1055/s-2003-40349 CR - D. Crich, Chemistry of glycosyl triflates:Synthesis of β-mannopyranosides. Journal of Carbohydrate Chemistry 21 (2002) 663-686. https://doi.org/10.1081/CAR-120016486 CR - M.M. Matin, M.M.H. Bhuiyan, E. Kabir, A.F.M. Sanaullah, M.A. Rahman, M.E. Hossain, M. Uzzaman, Synthesis, characterization, ADMET, PASS predication, and antimicrobial study of 6-O-lauroyl mannopyranosides. Journal of Molecular Structure 1195 (2019) 189-197. https://doi.org/10.1016/j.molstruc.2019.05.102 CR - B. Ren, L. Zhang, M. Zhang, Progress on selective acylation of carbohydrate hydroxyl groups. Asian Journal Organic Chemistry 8 (2019) 1813-1823. https://doi.org/10.1002/ajoc.201900400 CR - M.M. Matin, T. Sharma, S.G. Sabharwal, D.D. Dhavale, Synthesis and evaluation of glycosidase inhibitory activity of 5-hydroxy substituted isofagomine analogues. Organic & Biomolecular Chemistry 3 (2005) 1702-1707. https://doi.org/10.1039/b418283a CR - M.M. Matin, P. Chakraborty, Synthesis, spectral and DFT characterization, PASS predication, antimicrobial, and ADMET studies of some novel mannopyranoside esters. Journal of Applied Science & Process Engineering 7(2) (2020) 572-586. https://doi.org/10.33736/jaspe.2603.2020 CR - A.R. Buzatu, A.E. Frissen, L.A.M. van den Broek, A. Todea, M. Motoc, C.G. Boeriu, Chemoenzymatic synthesis of new aromatic esters of mono- and oligosaccharides. Processes 8 (2020) 1638. https://doi.org/10.3390/pr8121638 CR - M.M. Matin, M.S. Hasan, M. Uzzaman, M.M.H. Bhuiyan, S.M. Kibria, M.E. Hossain, M.H.O. Roshid, Synthesis, spectroscopic characterization, molecular docking, and ADMET studies of mannopyranoside esters as antimicrobial agents. Journal of Molecular Structure 1222 (2020) 128821. https://doi.org/10.1016/j.molstruc.2020.128821 CR - A. Richel, P. Laurent, B. Wathelet, J.–P. Wathelet, M. Paquot, Microwave-assisted conversion of carbohydrates. State of the art and outlook. Comptes Rendus Chimie 14 (2011) 224-234. https://doi.org/10.1016/j.crci.2010.04.004 CR - S.R. Kim, Y.C. Kim, Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of Scrophularia buergeriana. Phytochemistry 54 2000, 503-509. https://doi.org/10.1016/s0031-9422(00)00110-2 CR - X.Z. Dong, C.L. Huang, B.Y. Yu, Y. Hu, L.H. Mu, P. Liu, Effect of Tenuifoliside A isolated from Polygala tenuifolia on the ERK and PI3K pathways in C6 glioma cells. Phytomedicine 21 (2014) 1178-1188. https://doi.org/10.1016/j.phymed.2014.04.022 CR - Y. Tian, W. Liu, Y. Lu, Y. Wang, X. Chen, S. Bai, Y. Zhao, T. He, F. Lao, Y. Shang, Y. Guo, G. She, Naturally occurring cinnamic acid sugar ester derivatives. Molecules 21 (2016) 1402. https://doi.org/10.3390/molecules21101402 CR - M. Mihoub, A. Pichette, B. Sylla, C. Gauthier, J. Legault, Bidesmosidic betulin saponin bearing L-rhamnopyranoside moieties induces apoptosis and inhibition of lung cancer cells growth in vitro and in vivo. PLoS ONE 13(3) (2018) 0193386. https://doi.org/10.1371/journal.pone.0193386 CR - A.K.M.S. Kabir, M.M. Matin, A. Hossain, M.A. Sattar, Synthesis and antimicrobial activities of some rhamnopyranoside derivatives. Journal of Bangladesh Chemical Society 16(2) 2003, 85-93. CR - M.M. Matin, M. Ibrahim, Synthesis of some methyl 4-O-octanoyl-α-L-rhamnopyranoside derivatives. Journal of Applied Sciences Research 6(10) (2010) 1527-1532. CR - M.M. Matin, M. Ibrahim, M.S. Rahman, Antimicrobial evaluation of methyl 4-O-acetyl-α-L-rhamnopyranoside derivatives. The Chittagong University Journal of Biological Sciences 3(1&2) (2008) 33-43. http://dx.doi.org/10.3329/cujbs.v3i1.13404 CR - M.M. Matin, M.H.O. Roshid, S.C. Bhattacharjee, A.K.M.S. Azad, PASS predication, antiviral, in vitro antimicrobial, and ADMET studies of rhamnopyranoside esters. Medical Research Archives 8(7) (2020) 2165. https://doi.org/10.18103/mra.v8i7.2165 CR - J. Qian, D. Hunkler, H. Rimpler, Iridoid-related aglycone and its glycosides from Scrophularia ningpoensis. Phytochemistry 31 (1992) 905-911. https://doi.org/10.1016/0031-9422(92)80037-F CR - J.A. Duck, E.S. Ayensu, 1985, Medical Plants of China. Algonac, MI, p. 599. CR - F.O. Akong, S. Bouquillon, Efficient syntheses of bolaform surfactants from l-rhamnose and/or 3-(4-hydroxyphenyl)propionic acid. Green Chemistry 17 (2015) 3290-3300. https://doi.org/10.1039/C5GC00448A CR - X.–D. Yang, Z.–Y. Li, S.–X. Mei, J.–F. Zhao, H.–B. Zhang, L. Li, Two new phenylpropanoid esters of rhamnose from Lagotis yunnanensis. Journal of Asian Natural Products Research 5(3) (2003) 223-226. https://doi.org/10.1080/1028602031000093366 CR - G.M. Lipkind, A.S. Shashkov, O.A. Nechaev, V.I. Torgov, V.N. Shibaev, N.K. Kochetkov, Conformations of branched trisaccharides with vicinal substitution according to the nuclear Overhauser effect and theoretical calculations. III. The spectra of 13C-NMR and trisaccharides conformation with galactose residue in a node branching. Bioorg. Khim. 15 (1989) 1366-1374. CR - G.M. Lipkind, N.E. Nifantev, A.S. Shashkov, N.K. Kochetkov, NMR and conformational study of branched oligosaccharides containing 2,3-disubstituted residues of α-L-rhamnose. Canadian Journal of Chemistry 68 (1990) 1238-1250. https://doi.org/10.1139/v90-192 CR - R. Pendrill, L. Eriksson, G. Widmalma, Methyl 4-O-benzyl-α-L-rhamnopyranoside. Acta Crystallographica Section E 70 (2014) o561–o562. https://doi.org/10.1107/S1600536814007922 CR - R.A. Mendes, S.K.C. Almeida, I.N. Soares, C.A. Barboza, R.G. Freitas, A. Brown, G.L.C. de Souza, A computational investigation on the antioxidant potential of myricetin 3,4-di-O-α-L-rhamnopyranoside. Journal of Molecular Modeling 24 (2018) 133. https://doi.org/10.1007/s00894-018-3663-2 CR - M.M. Matin, M.M.H. Bhuiyan, A.K.M.S. Azad, N. Akther, Design and synthesis of benzyl 4-O-lauroyl-α-L-rhamnopyranoside derivatives as antimicrobial agents. Current Chemistry Letters 6(1) (2017) 31-40. https://doi.org/10.5267/j.ccl.2016.10.001 CR - M.M. Matin, A.R. Nath, O. Saad, M.M.H. Bhuiyan, F.A. Kadir, S.B. Abd Hamid, A.A. Alhadi, M.E. Ali, W.A. Yehye, Synthesis, PASS-predication and in vitro antimicrobial activity of benzyl 4-O-benzoyl-α-L-rhamnopyranoside derivatives. International Journal of Molecular Sciences 17(9) (2016) 1412. https://doi.org/10.3390/ijms17091412 CR - M.M. Matin, Synthesis and antimicrobial study of some methyl 4-O-palmitoyl-α-L-rhamnopyranoside derivatives. Orbital: The Electronic Journal of Chemistry 6(1) (2014) 20-28. https://doi.org/10.17807/orbital.v6i1.553 CR - M.M. Matin, M.Z. Iqbal, Methyl 4-O-(2-chlorobenzoyl)-α-L-rhamnopyranosides: Synthesis, characterization, and thermodynamic studies. Orbital: The Electronic Journal of Chemistry 13(1) (2021) 19-27. http://dx.doi.org/10.17807/orbital.v13i1.1532 CR - M.M. Matin, N. Islam, A. Siddika, S.C. Bhattacharjee, Regioselective synthesis of some rhamnopyranoside esters for PASS predication, and ADMET studies. Journal of the Turkish Chemical Society Section A: Chemistry 8(1) (2021) 363-374. https://doi.org/10.18596/jotcsa.829658 CR - MM Matin, M Uzzaman, SA Chowdhury, MMH Bhuiyan, In vitro antimicrobial, physicochemical, pharmacokinetics, and molecular docking studies of benzoyl uridine esters against SARS-CoV-2 main protease. Journal of Biomolecular Structure and Dynamics (2020). https://doi.org/10.1080/07391102.2020.1850358. CR - A.K.M.S. Kabir, M.M. Matin, Regioselective monoacylation of a derivative of L-rhamnose. Journal of Bangladesh Academy of Sciences 21(1) (1997) 83-88. CR - M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R. L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J. B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox, Gaussian 09W, Revision D.01, Gaussian, Inc, Wallingford CT, 2013. CR - A. D. Becke, Density-functional thermochemistry. III. The role of exact exchange. The Journal of Chemical Physics 98 (1993) 5648-5652. https://doi.org/10.1063/1.464913 CR - C. Lee, W. Yang, R. G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physics Review B37 (1988) 785-789. https://doi.org/10.1103/PhysRevB.37.785 CR - R. Ditchfield, W. J. Hehre, and J. A. Pople, Self-Consistent Molecular Orbital Methods. 9. Extended Gaussian-type basis for molecular-orbital studies of organic molecules. The Journal of Chemical Physics 54 (1971) 724. http://dx.doi.org/10.1063/1.1674902 CR - W.J. Hehre, R. Ditchfield, J.A. Pople, Self-Consistent Molecular Orbital Methods. 12. Further extensions of Gaussian-type basis sets for use in molecular-orbital studies of organic-molecules. The Journal of Chemical Physics 56 (1972) 2257-2261. http://dx.doi.org/10.1063/1.1677527 CR - T. Sawada, T. Hashimoto, H. Nakano, M. Shigematsu, H. Ishida, M. Kiso, Conformational study of α-N-acetyl-D-neuraminic acid by density functional theory. Journal of Carbohydrate Chemistry 25(5) (2006) 387-405. http://dx.doi.org/10.1080/07328300600778801 CR - M.A. Shalaby, F.R. Fronczek, E.S. Younathan, Structural analysis of methyl α-L-rhamnopyranoside in the solid state. Carbohydrate Research 258 (1994) 267-274. https://doi.org/10.1016/0008-6215(94)84092-X CR - M.A. Shalaby, F.R. Fronczek, E.S. Younathan, Conformational features of rhamnopyranose derivatives: The molecular structure of methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside. Carbohydrate Research 264(2) (1994) 173-180. https://doi.org/10.1016/S0008-6215(05)80003-5 CR - I. Noorbatcha, S. Hassan, A. Hamid, A. Hadi, K. Awang, Ab-initio geometry-optimization and NMR studies of chemical constituents of Piper sarmentosum. Malaysian Journal of Science 21 (2002) 143-147. CR - A. Kumer, M.N. sarker, S. Paul, The Thermophysical, HOMO, LUMO, vibrational spectroscopy and QSAR study of morpholinium formate and acetate ionic liquid salts using computational method. Turkish Computational and Theoretical Chemistry 3(2) (2019) 59-68. CR - M. Ali, M.H. Karim, M.M. Matin, Efficient synthetic technique, PASS predication, and ADMET studies of acylated n-octyl glucopyranosides. Journal of Applied Science & Process Engineering 8(1) (2021) 648-659. https://doi.org/10.33736/jaspe.2823.2021 CR - R.G. Pearson, Absolute electronegativity and hardness correlated with molecular orbital theory. Proc. Natl. Acad. Sci. USA., 83 (1986) 8440-8441. https://doi.org/10.1073/pnas.83.22.8440 CR - T. Koopmans, Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms. Physica 1 (1934) 104-113. https://doi.org/10.1016/S0031-8914(34)90011-2 CR - R.G. Parr, L.V. Szentpaly, S. Liu, Electrophilicity index. Journal of the American Chemical Society 121 (1999) 1922-1924. https://doi.org/10.1021/ja983494x CR - R.G. Parr, R.G. Pearson, Absolute hardness: companion parameter to absolute electronegativity. Journal of the American Chemical Society 105 (1983) 7512-7516. https://doi.org/10.1021/ja00364a005 UR - https://doi.org/10.33435/tcandtc.914768 L1 - https://dergipark.org.tr/en/download/article-file/1701943 ER -