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Synthesis of Novel 1,2,3-Triazolyl L-Serinol Palmitoyl Muramyl Dipeptide Derivatives
Corresponding Author(s) : Halmuthur M. Sampath Kumar
Asian Journal of Chemistry,
Vol. 35 No. 3 (2023): Vol 35 Issue 3, 2023
Abstract
In this research, a structural variant of muramyl dipeptide (MDP) is designed wherein, the entire N-acetyl group was replaced by a bio-isosteric 1,2,3-triazole moiety with serinol lipid substitution at 4th position. The protecting groups such as benzyl and benzylidine were removed sequentially to evolve three novel derivatives with increasing polarity as seen in the MDP-lipid 21-23 derivatives. A synthesis strategy involving triazolyl click chemistry to combine MDP scaffold to the serinol lipid head group is developed. The new derivatives were characterized using NMR, ESI-MS and MALDI. Preliminary data from in vitro screening of the compounds inferred the immuno-potentiating properties.
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- J. Maharana, B. Dehury, J.R. Sahoo, I. Jena, A. Bej, D. Panda, B.R. Sahoo, M.C. Patra and S.K. Pradhan, Mol. BioSyst., 11, 2324 (2015); https://doi.org/10.1039/C5MB00212E
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- M.J.M. Bertrand, K. Doiron, K. Labbé, R.G. Korneluk, P.A. Barker and M. Saleh, Immunity, 30, 789 (2009); https://doi.org/10.1016/j.immuni.2009.04.011
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- P. Garner and J.M. Park, Org. Synth., 70, 18 (2003); https://doi.org/10.1002/0471264180.os070.03
- S. Vemireddy, M.C. Preethi Pallavi and H.M. Sampath Kumar, Carbohydr. Polym., 190, 129 (2018); https://doi.org/10.1016/j.carbpol.2018.02.073
- D.J. Wardrop and J. Fritz, Organ. Lett., 8, 3659 (2006); https://doi.org/10.1021/ol0609053
- X. Liang, J. Andersch and M. Bols, J. Chem. Soc., Perkin Trans. 1, 2136 (2001); https://doi.org/10.1039/b101054i
- S. Wang, S.A. Cameron, K. Clinch, G.B. Evans, Z. Wu, V.L. Schramm and P.C. Tyler, J. Am. Chem. Soc., 137, 14275 (2015); https://doi.org/10.1021/jacs.5b06110
- V.R. Jupally, R. Kota, E. Van Dornshuld, D.L. Mattern, G.S. Tschumper, D.-e. Jiang and A. Dass, J. Am. Chem. Soc., 133, 20258 (2011); https://doi.org/10.1021/ja206436x
- D. Bhunia, P.M.C. Pallavi, S.R. Bonam, S.A. Reddy, Y. Verma and M.S.K. Halmuthur, Arch. Pharm., 348, 689 (2015); https://doi.org/10.1002/ardp.201500143
- F. Naaz, M.C. Preeti Pallavi, S. Shafi, N. Mulakayala, M.S. Yar and H.M. Sampath Kumar, Bioorg. Chem., 81, 1 (2018); https://doi.org/10.1016/j.bioorg.2018.07.029
- D.M. Reddy, J. Srinivas, G. Chashoo, A.K. Saxena and H.M. Sampath Kumar, Eur. J. Med. Chem., 46, 1983 (2011); https://doi.org/10.1016/j.ejmech.2011.02.016
- W.-C. Cheng, T.-Y. You, Z.-Z. Teo, A.A. Sayyad, J. Maharana, C.-W. Guo, P.-H. Liang, C.-S. Lin and F.-C. Meng, Chem. Asian J., 15, 3836 (2020); https://doi.org/10.1002/asia.202001003
- T.B. Mhamane, S. Sambyal, S. Vemireddy, I.A. Khan, S. Shafi and H.M. Sampath Kumar, Bioorg. Chem., 111, 104838 (2021); https://doi.org/10.1016/j.bioorg.2021.104838
References
J. Maharana, B. Dehury, J.R. Sahoo, I. Jena, A. Bej, D. Panda, B.R. Sahoo, M.C. Patra and S.K. Pradhan, Mol. BioSyst., 11, 2324 (2015); https://doi.org/10.1039/C5MB00212E
J. Maharana, B.R. Sahoo, A. Bej, I. Jena, A. Parida, J.R. Sahoo, B. Dehury, M.C. Patra, S.R. Martha, S. Balabantray, S.K. Pradhan and B.K. Behera, PLoS One, 10, e0121415 (2015); https://doi.org/10.1371/journal.pone.0121415
M.J.M. Bertrand, K. Doiron, K. Labbé, R.G. Korneluk, P.A. Barker and M. Saleh, Immunity, 30, 789 (2009); https://doi.org/10.1016/j.immuni.2009.04.011
J.E. Melnyk, V. Mohanan, A.K. Schaefer, C.-W. Hou and C.L. Grimes, J. Am. Chem. Soc., 137, 6987 (2015); https://doi.org/10.1021/jacs.5b01607
P.R.S. Reddy, S. Sambyal, T.B. Mhamane, V. Sravanthi, S. Shafi, I.A. Khan and H.M. Sampath Kumar, Bioorg. Med. Chem., 66, 116781 (2022); https://doi.org/10.1016/j.bmc.2022.116781
P. Garner and J.M. Park, Org. Synth., 70, 18 (2003); https://doi.org/10.1002/0471264180.os070.03
S. Vemireddy, M.C. Preethi Pallavi and H.M. Sampath Kumar, Carbohydr. Polym., 190, 129 (2018); https://doi.org/10.1016/j.carbpol.2018.02.073
D.J. Wardrop and J. Fritz, Organ. Lett., 8, 3659 (2006); https://doi.org/10.1021/ol0609053
X. Liang, J. Andersch and M. Bols, J. Chem. Soc., Perkin Trans. 1, 2136 (2001); https://doi.org/10.1039/b101054i
S. Wang, S.A. Cameron, K. Clinch, G.B. Evans, Z. Wu, V.L. Schramm and P.C. Tyler, J. Am. Chem. Soc., 137, 14275 (2015); https://doi.org/10.1021/jacs.5b06110
V.R. Jupally, R. Kota, E. Van Dornshuld, D.L. Mattern, G.S. Tschumper, D.-e. Jiang and A. Dass, J. Am. Chem. Soc., 133, 20258 (2011); https://doi.org/10.1021/ja206436x
D. Bhunia, P.M.C. Pallavi, S.R. Bonam, S.A. Reddy, Y. Verma and M.S.K. Halmuthur, Arch. Pharm., 348, 689 (2015); https://doi.org/10.1002/ardp.201500143
F. Naaz, M.C. Preeti Pallavi, S. Shafi, N. Mulakayala, M.S. Yar and H.M. Sampath Kumar, Bioorg. Chem., 81, 1 (2018); https://doi.org/10.1016/j.bioorg.2018.07.029
D.M. Reddy, J. Srinivas, G. Chashoo, A.K. Saxena and H.M. Sampath Kumar, Eur. J. Med. Chem., 46, 1983 (2011); https://doi.org/10.1016/j.ejmech.2011.02.016
W.-C. Cheng, T.-Y. You, Z.-Z. Teo, A.A. Sayyad, J. Maharana, C.-W. Guo, P.-H. Liang, C.-S. Lin and F.-C. Meng, Chem. Asian J., 15, 3836 (2020); https://doi.org/10.1002/asia.202001003
T.B. Mhamane, S. Sambyal, S. Vemireddy, I.A. Khan, S. Shafi and H.M. Sampath Kumar, Bioorg. Chem., 111, 104838 (2021); https://doi.org/10.1016/j.bioorg.2021.104838