Research Article
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The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study

Year 2021, , 39 - 50, 15.06.2021

Farzana Islam , Md. Rezaur Rahman Mohammed Mahbubul Matin

https://doi.org/10.33435/tcandtc.914768
Cited By: 6

Abstract

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.

Keywords

Conformational study DFT optimization MEP Rhamnopyranoside Sugar esters (SEs) Thermodynamic properties

Supporting Institution

Research and Publication Cell, University of Chittagong, Bangladesh

Project Number

2021, Special

Thanks

We are thankful to Mr Ajoy Kumer, European University of Bangladesh for helpful discussion about this study.

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Year 2021, , 39 - 50, 15.06.2021

Farzana Islam , Md. Rezaur Rahman Mohammed Mahbubul Matin

https://doi.org/10.33435/tcandtc.914768
Cited By: 6

Abstract

Project Number

2021, Special

References

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  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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.
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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.
  • 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.
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There are 57 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Research Article
Authors

Farzana Islam 0000-0001-6056-0972

Md. Rezaur Rahman This is me 0000-0002-7151-0687

Mohammed Mahbubul Matin 0000-0003-4965-2280

Project Number 2021, Special
Publication Date June 15, 2021
Submission Date April 13, 2021
Published in Issue Year 2021

Cite

APA Islam, F., Rahman, M. . R., & Matin, M. M. (2021). The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study. Turkish Computational and Theoretical Chemistry, 5(1), 39-50. https://doi.org/10.33435/tcandtc.914768
AMA Islam F, Rahman MR, Matin MM. The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study. Turkish Comp Theo Chem (TC&TC). June 2021;5(1):39-50. doi:10.33435/tcandtc.914768
Chicago Islam, Farzana, Md. Rezaur Rahman, and Mohammed Mahbubul Matin. “The Effects of Protecting and Acyl Groups on the Conformation of Benzyl α-L-Rhamnopyranosides: An in Silico Study”. Turkish Computational and Theoretical Chemistry 5, no. 1 (June 2021): 39-50. https://doi.org/10.33435/tcandtc.914768.
EndNote Islam F, Rahman MR, Matin MM (June 1, 2021) The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study. Turkish Computational and Theoretical Chemistry 5 1 39–50.
IEEE F. Islam, M. . R. Rahman, and M. M. Matin, “The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study”, Turkish Comp Theo Chem (TC&TC), vol. 5, no. 1, pp. 39–50, 2021, doi: 10.33435/tcandtc.914768.
ISNAD Islam, Farzana et al. “The Effects of Protecting and Acyl Groups on the Conformation of Benzyl α-L-Rhamnopyranosides: An in Silico Study”. Turkish Computational and Theoretical Chemistry 5/1 (June 2021), 39-50. https://doi.org/10.33435/tcandtc.914768.
JAMA Islam F, Rahman MR, Matin MM. The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study. Turkish Comp Theo Chem (TC&TC). 2021;5:39–50.
MLA Islam, Farzana et al. “The Effects of Protecting and Acyl Groups on the Conformation of Benzyl α-L-Rhamnopyranosides: An in Silico Study”. Turkish Computational and Theoretical Chemistry, vol. 5, no. 1, 2021, pp. 39-50, doi:10.33435/tcandtc.914768.
Vancouver Islam F, Rahman MR, Matin MM. The effects of protecting and acyl groups on the conformation of benzyl α-L-rhamnopyranosides: An in silico study. Turkish Comp Theo Chem (TC&TC). 2021;5(1):39-50.

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Journal Full Title: Turkish Computational and Theoretical Chemistry


Journal Abbreviated Title: Turkish Comp Theo Chem (TC&TC)