A mild methylation method is detailed in this work. It uses 1N NaOH to deprotonate primary and secondary hydroxyl groups for short time. Excess 1N NH4OH (1.00 ml, pH 11.4) is added, followed by NaHCO3 to make the carbonate esters by nucleophilic substitution of the deprotonated primary and secondary OH groups. The reaction conditions include; ambient temperature and for an appropriate time. Then NaBH4 is added and the reaction conditions are; standing at ambient temperature for at least 4 hours. This converts the carbonate esters to the methyl ethers. Work-up includes transferring the methylated switchgrass leaf section to a vial containing 1N HCl (1.00 ml). The leaf needs to be submerged in the acid. The reaction conditions include; heating the reaction vessel at 72°C, for 4 days. The contents of the vial are reduced in volume to syrup with a stream of air. The mixture dissolves completely in methanol. Mass spectrometry is done on a methanol solution in the negative ion ESI mode. The mass spectral interpretation reveals the presence of methylated glucan amimo acids and glucan dipeptides. The molecules identified were per-O-methylated glucans linked to either serine or asparagine through a di-(hydrido) di-phospho di-hydratephe moeity. It is possible that one ion is derived from a phosphorylated tyrosine linked to either the serine or asparagine linked to an originally di-phospho cellulo-glucan.
| Published in | Plant (Volume 8, Issue 1) |
| DOI | 10.11648/j.plant.20200801.12 |
| Page(s) | 10-16 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2024. Published by Science Publishing Group |
Mass Spectrometry, Novel Mild Methylation Method, Cellulo-dipeptides, Per-O-methyl Cellulo-peptides, Glucan-Peptide Linkage
| [1] | Bjorndal, H.; Hellerqvist, C.; Lindberg, B.; Svensson, S.; Gas-liquid chromatography and mass spectrometry in methylation analysis of polysaccharides; Angewandte Chemie International Edition in English 9 (1) 610-619 (1970). |
| [2] | Harris, P.; Henry, R.; Blakeney, A.; Stone, B.; An improved procedure for the methylation of oligossccharides and polysaccharides Carbohydrate research 127 (1) 59-73 (1984). |
| [3] | Sowden, J.; The saccharinic acids Advances in carbohydrate chemistry 12 55-79 (1957). |
| [4] | Hough, L.; Priddle, J.; Theobald, R.; The carbonates and thiocarbonates of carbohydrates; Advances in carbohydrate chemistry 15, 91-158 (1961). |
| [5] | Madson, M.; Manufacturing of MeOH, formaldehyde, formic acid and ammonium pentaborate tetrahydrate from carbon dioxide patent US 8,695,355 B2 (2014). |
| [6] | Madson, M.; Method of discerning substitution of carbohydrate esters patent US 9,726,671 B2 (2017). |
| [7] | Glinski, M.; Weckworth, W.; The role of mass spectrometry in plant systems Mass spectrometry reviews 25 (2) 173-214 (2006). |
| [8] | McQuire, C.; Roseman, S.; Enzymatic synthesis of the protein hexosamine linkage in sheep submaxillary mucin; Journal of biological chemistry 242 (16) 3745-3747 (1967). |
| [9] | Zhang, Y.; Zhang, P.; West, C.; A linking function for the cellulose-binding protein SPBS in the spore of Dictyostelium aiscoideum Journal of cell science 112 (23) 4367-4377 (1999). |
| [10] | Shinohara, H.; Ogawa, H.; Matsubaychi, H-S.; Tyrosine sulfated glycopeptides involved in cellular proliferation and expansion Proceedings of the National Academy of Sciences, USA 104 (46) 18333-18338 (2007). |
| [11] | Denu, J.; Stuckey, J.; Saper, M.; Dixon, J.; Form and function in protein dephosphorylation Cell 87 (3) 361-364 (1996). |
| [12] | Nadam, D.; Knutson, E.; Lo, R.; Renig, N.; Exploration of cell signaling machinery activation of macrophage phospho tyrosine phosphatases as a mechanism of molecular microbial pathogenesis Journal of leukocyte biology 67 (4) 464-470 (2000). |
| [13] | Mitho, S.; Boersema, I.; Berke, L.; Snel, B.; Heck, A.; Menke, E.; Targeted quantitative phospho proteome approach for the detection of phospho-tyrosine signaling in plants Journal of proteome research 1 (1) 438-448 (2012). |
| [14] | Christus, J.; Madson, M.; Possible treatment of Mycobacterium lepramatous with bovine milk World journal of food science and technology 2 (1) 55-61 (2018). |
| [15] | Christus, J.; Madson, M.; Possible mimics of Duffy Binding Protein-ll for Plasmodium vivax binding endothelial cells or binding of Plasmodium falciparum by mimicking epitope on erythrocyte binding antigen-175 A World journal of food science and technology 2 (2) 44-51 (2018). |
| [16] | Christus, J.; Madson, M.; Preparation of possible P selectin inhibitor from bovine thyroglobulin, (di-hydrido) sulfo hydrate 1,5 anhydro L-fucitol. World journal of food science and technology accepted for publication (2019). |
| [17] | Richmond, T.; Sommerville, C.; The cellulose synthase superfamily Plant physiology 124 (2) 495-498 (2000). |
| [18] | Endler, D.; Persson, S. Cellulose synthases and synthesis in Arabidopsis Molecular plant 4 (2) 199-211 (2011). |
APA Style
Jesus’ Christus, Michael Arden Madson. (2020). A Mild Methylation of Whole Leaf Producing Per-O-methyl Cellulo Di-phospho Amino Acid (Dipeptide). Plant, 8(1), 10-16. https://doi.org/10.11648/j.plant.20200801.12
ACS Style
Jesus’ Christus; Michael Arden Madson. A Mild Methylation of Whole Leaf Producing Per-O-methyl Cellulo Di-phospho Amino Acid (Dipeptide). Plant. 2020, 8(1), 10-16. doi: 10.11648/j.plant.20200801.12
AMA Style
Jesus’ Christus, Michael Arden Madson. A Mild Methylation of Whole Leaf Producing Per-O-methyl Cellulo Di-phospho Amino Acid (Dipeptide). Plant. 2020;8(1):10-16. doi: 10.11648/j.plant.20200801.12
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Download@article{10.11648/j.plant.20200801.12,
author = {Jesus’ Christus and Michael Arden Madson},
title = {A Mild Methylation of Whole Leaf Producing Per-O-methyl Cellulo Di-phospho Amino Acid (Dipeptide)},
journal = {Plant},
volume = {8},
number = {1},
pages = {10-16},
doi = {10.11648/j.plant.20200801.12},
url = {https://doi.org/10.11648/j.plant.20200801.12},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.plant.20200801.12},
abstract = {A mild methylation method is detailed in this work. It uses 1N NaOH to deprotonate primary and secondary hydroxyl groups for short time. Excess 1N NH4OH (1.00 ml, pH 11.4) is added, followed by NaHCO3 to make the carbonate esters by nucleophilic substitution of the deprotonated primary and secondary OH groups. The reaction conditions include; ambient temperature and for an appropriate time. Then NaBH4 is added and the reaction conditions are; standing at ambient temperature for at least 4 hours. This converts the carbonate esters to the methyl ethers. Work-up includes transferring the methylated switchgrass leaf section to a vial containing 1N HCl (1.00 ml). The leaf needs to be submerged in the acid. The reaction conditions include; heating the reaction vessel at 72°C, for 4 days. The contents of the vial are reduced in volume to syrup with a stream of air. The mixture dissolves completely in methanol. Mass spectrometry is done on a methanol solution in the negative ion ESI mode. The mass spectral interpretation reveals the presence of methylated glucan amimo acids and glucan dipeptides. The molecules identified were per-O-methylated glucans linked to either serine or asparagine through a di-(hydrido) di-phospho di-hydratephe moeity. It is possible that one ion is derived from a phosphorylated tyrosine linked to either the serine or asparagine linked to an originally di-phospho cellulo-glucan.},
year = {2020}
}
TY - JOUR T1 - A Mild Methylation of Whole Leaf Producing Per-O-methyl Cellulo Di-phospho Amino Acid (Dipeptide) AU - Jesus’ Christus AU - Michael Arden Madson Y1 - 2020/04/28 PY - 2020 N1 - https://doi.org/10.11648/j.plant.20200801.12 DO - 10.11648/j.plant.20200801.12 T2 - Plant JF - Plant JO - Plant SP - 10 EP - 16 PB - Science Publishing Group SN - 2331-0677 UR - https://doi.org/10.11648/j.plant.20200801.12 AB - A mild methylation method is detailed in this work. It uses 1N NaOH to deprotonate primary and secondary hydroxyl groups for short time. Excess 1N NH4OH (1.00 ml, pH 11.4) is added, followed by NaHCO3 to make the carbonate esters by nucleophilic substitution of the deprotonated primary and secondary OH groups. The reaction conditions include; ambient temperature and for an appropriate time. Then NaBH4 is added and the reaction conditions are; standing at ambient temperature for at least 4 hours. This converts the carbonate esters to the methyl ethers. Work-up includes transferring the methylated switchgrass leaf section to a vial containing 1N HCl (1.00 ml). The leaf needs to be submerged in the acid. The reaction conditions include; heating the reaction vessel at 72°C, for 4 days. The contents of the vial are reduced in volume to syrup with a stream of air. The mixture dissolves completely in methanol. Mass spectrometry is done on a methanol solution in the negative ion ESI mode. The mass spectral interpretation reveals the presence of methylated glucan amimo acids and glucan dipeptides. The molecules identified were per-O-methylated glucans linked to either serine or asparagine through a di-(hydrido) di-phospho di-hydratephe moeity. It is possible that one ion is derived from a phosphorylated tyrosine linked to either the serine or asparagine linked to an originally di-phospho cellulo-glucan. VL - 8 IS - 1 ER -
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