Login Register Cart 0
Generic placeholder image

Current Bioactive Compounds

Editor-in-Chief

ISSN (Print): 1573-4072
ISSN (Online): 1875-6646

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Synthesis of New Glycosylamine Derivatives based on Carbohydrates

Author(s): Hadi Jabbari*

Volume 20, Issue 2, 2024

Published on: 08 September, 2023

Article ID: e100823219613 Pages: 11

DOI: 10.2174/1573407219666230810094657

Price: $65

Abstract

Background: Glycosylamine play an important role in living organisms. Most plants store their chemical resources in the form of inactive glycosides, which are broken down and converted into sugar in the body of herbivores by hydrolyzing enzymes. Glycosylamine are obtained from the secondary metabolism of plants and consist of two parts. One part of it contains sugar like glucose and is inactive in most substances, and has a good effect on the solubility of the glycosylamine derivatives and its absorption and even its transfer from one organ to another. The therapeutic effect is related to the second part, which is called aglycan (or aglucan). Glycosylamine derivatives form a large group of valuable medicinal substances, which at the same time include some of the most dangerous and toxic substances in nature. These substances are present in many groups of flowering plants. Glycosides are made in different ways in different metabolic pathways. These materials have a complex and special chemical structure and leave special effects on the human body. Glycosylamine derivatives are called O-glycosid, N-glycosid, S-glycosid in terms of atoms coupling to anomeric carbon. Carbohydrate esterification reaction to prepare new glycosylamine derivatives is one of the most important carbohydrate reactions. The anomeric position of carbohydrates with strong leaving groups is very important for the preparation of glycosides. Preparation of glycosylamine derivatives based on acetylated carbohydrates is the main purpose of this article. Different carbohydrates were acetylated under mild conditions and high yields. The anomeric position was deacetylated by a magnesium oxide heterogeneous catalyst in methanol solvent. In order to prepare new glycosides acetylated/ deacytylated carbohydrate reacted with N-Methyl-(naphtha-2- ylmethoxy)amine. The final product was identified by various spectroscopic methods.

Methods: Anhydrous sodium acetate (4 g) and α-D-glucose (28 mg, 5 g) were mixed. The mixture was transferred to a 200 ml Round-bottom flask . Acetic acid (260 mg, 25 ml) was added to the reaction mixture. The reaction mixture was heated in a boiling water bath for 2 h until complete dissolution of the glucose. Then 100 ml of ice was added. After 1 hour, White crystals formed and were washed with cold water. And then 1 mol of glucose pentaacetate per 50 ml of methanol was dissolved by a magnetic stirrer. After thatMgO (0.2gr) was added to the reaction mixture. The reaction mixture was refluxed at room temperature within 4-5 hours. After 5 hours, the solvent was removed and separated by chromatography. It is then washed with hexane and crystallized by etherhexane. And the final step reacted with N-Methyl- (naphtha-2-ylmethoxy) amine in order to prepare new glycosylamine derivatives.

Results: Magnesium oxide in methanol solvent is one of the best effective catalysts in the deacetylation of the anomer position of acetylated carbohydrates. It is done under ambient temperature and in very easy conditions and makes carbohydrates susceptible to extensive chemical reactions. One of these reactions is the formation of glycosides. Various carbohydrates are acetylated by acetic anhydride in the presence of sodium acetate, and the anomeric position is deacetylated by a heterogeneous catalyst. In order to prepare N-glycoside, the glycosides are reacted with N-alkoxy N-methylglycosyl amine. The final products are identified by various spectroscopic methods.

Conclusion: Glucose, mannose, for example, were acetylated by acetic anhydride in the presence of sodium acetate. And the anomeric position of pentaacetate glucose was selectively deacetylated with magnesium oxide in a methanol solvent. Then, the reaction for the preparation of glycosylamine derivatives was carried out under very mild and easy conditions. The aminoglycosides synthesized in this article are used as raw materials for the synthesis of a wide range of antibacterials.

[1]
Jabbari, H. Synthesis of carbohydrate esters and investigation reaction of Phosphoryl chloride from anomeric position of Per-Acetylated Carbohydrates. Arch. Pharm. Pract., 2020, 1(2), 71-76.
[2]
Jabbari, H. Acetylation of carbohydrates and selective anomeric deacetylation by MgO/MeOH. j. chemical oggi chemistry Today, 2018, 1(2), 1-5.
[3]
Tiwari, P.; Misra, A.K. Selective removal of anomeric O-acetate groups in carbohydrates using HClO4–SiO2. Tetrahedron Lett., 2006, 47(21), 3573-3576.
[http://dx.doi.org/10.1016/j.tetlet.2006.03.050]
[4]
Tran, A.T.; Deydier, S.; Bonnaffé, D.; Le Narvor, C. Regioselective green anomeric deacetylation catalyzed by lanthanide triflates. Tetrahedron Lett., 2008, 49(13), 2163-2165.
[http://dx.doi.org/10.1016/j.tetlet.2008.01.106]
[5]
Calvaresi, E.C.; Hergenrother, P.J. Glucose conjugation for the specific targeting and treatment of cancer. Chem. Sci., 2013, 4(6), 2319-2333.
[http://dx.doi.org/10.1039/c3sc22205e] [PMID: 24077675]
[6]
Wang, Z.D.; Mo, Y.; Chiou, C.L.; Liu, M. A simple preparation of 2,3,4,6-tetra-o-acyl-gluco-, galacto- and mannopyranoses and relevant theoretical study. Molecules, 2010, 15(1), 374-384.
[http://dx.doi.org/10.3390/molecules15010374] [PMID: 20110897]
[7]
Herzig, J.; Nudelman, A. Regioselective heterogeneous O-deacylation of polyacylated sugars. Carbohydr. Res., 1986, 153(1), 162-167.
[http://dx.doi.org/10.1016/S0008-6215(00)90208-8]
[8]
Nahrstedt, A.; Davis, R.H. Occurrence, variation and biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in species of the Heliconiini (Insecta: Lepidoptera). Comp. Biochem. Physiol. B, 1983, 75(1), 65-73.
[http://dx.doi.org/10.1016/0305-0491(83)90041-X]
[9]
Gleadow, R.M.; Møller, B.L. Cyanogenic glycosides: Synthesis, physiology, and phenotypic plasticity. Annu. Rev. Plant Biol., 2014, 65(1), 155-185.
[http://dx.doi.org/10.1146/annurev-arplant-050213-040027] [PMID: 24579992]
[10]
Mukhopadhyay, B.; Field, R.A. A simple one-pot method for the synthesis of partially protected mono- and disaccharide building blocks using an orthoesterification–benzylation–orthoester rearrangement approach. Carbohydr. Res., 2003, 338(20), 2149-2152.
[http://dx.doi.org/10.1016/S0008-6215(03)00349-5] [PMID: 14505883]
[11]
Zhang, Z.; Wong, C.H. Regioselective benzoylation of sugars mediated by excessive Bu2SnO: Observation of temperature promoted mi-gration. Tetrahedron, 2002, 58(32), 6513-6519.
[http://dx.doi.org/10.1016/S0040-4020(02)00661-0]
[12]
Kaya, E.; Sonmez, F.; Kucukislamoglu, M.; Nebioglu, M. Selective anomeric deacetylation using zinc acetate as catalyst. Chem. Pap., 2012, 66(4), 312-315.
[http://dx.doi.org/10.2478/s11696-012-0143-5]
[13]
Park, S.; Hsieh, H.W.; Gervay-Hague, J. Anomeric O-functionalization of carbohydrates for chemical conjugation to vaccine constructs. Molecules, 2018, 23(7), 1742.
[http://dx.doi.org/10.3390/molecules23071742] [PMID: 30018207]
[14]
Hsu, C.H.; Hung, S.C.; Wu, C.Y.; Wong, C.H. Toward automated oligosaccharide synthesis. Angew. Chem. Int. Ed., 2011, 50(50), 11872-11923.
[http://dx.doi.org/10.1002/anie.201100125] [PMID: 22127846]
[15]
Park, S.S.; Gervay-Hague, J. Synthesis of partially O-acetylated N-acetylneuraminic acid using regioselective silyl exchange technology. Org. Lett., 2014, 16(19), 5044-5047.
[http://dx.doi.org/10.1021/ol502389g] [PMID: 25247390]
[16]
Popadynec, M.; Baradaran-Heravi, A.; Alford, B.; Cameron, S.A.; Clinch, K.; Mason, J.M.; Rendle, P.M.; Zubkova, O.V.; Gan, Z.; Liu, H.; Rebollo, O.; Whitfield, D.M.; Yan, F.; Roberge, M.; Powell, D.A. Reducing the toxicity of designer aminoglycosides as nonsense mutation readthrough agents for therapeutic targets. ACS Med. Chem. Lett., 2021, 12(9), 1486-1492.
[http://dx.doi.org/10.1021/acsmedchemlett.1c00349] [PMID: 34531957]
[17]
Yeh, Y.C.; Kim, H.J.; Liu, H. Mechanistic investigation of 1, 2-diol dehydration of paromamine catalyzed by the radical S-adenosyl-l-methionine enzyme AprD4. J. Am. Chem. Soc., 2021, 143(13), 5038-5043.
[http://dx.doi.org/10.1021/jacs.1c00076] [PMID: 33784078]
[18]
Rajasekaran, P.; Crich, D. Synthesis of gentamicin minor components: Gentamicin B1 and gentamicin X2. Org. Lett., 2020, 22(10), 3850-3854.
[http://dx.doi.org/10.1021/acs.orglett.0c01107] [PMID: 32343899]
[19]
Zada, S.L.; Baruch, B.B.; Simhaev, L.; Engel, H.; Fridman, M. Chemical modifications reduce auditory cell damage induced by aminoglycoside antibiotics. J. Am. Chem. Soc., 2020, 142(6), 3077-3087.
[http://dx.doi.org/10.1021/jacs.9b12420] [PMID: 31958945]
[20]
Jeanneret, R.A.; Dalton, C.E.; Gardiner, J.M. Synthesis of heparan sulfate-and dermatan sulfate-related oligosaccharides via iterative chemoselective glycosylation exploiting conformationally disarmed [2.2. 2] L-iduronic lactone thioglycosides. J. Org. Chem., 2019, 84(23), 15063-15078.
[http://dx.doi.org/10.1021/acs.joc.9b01594] [PMID: 31674785]
[21]
Sati, G.C.; Sarpe, V.A.; Furukawa, T.; Mondal, S.; Mantovani, M.; Hobbie, S.N.; Vasella, A.; Böttger, E.C.; Crich, D. Modification at the 2′-position of the 4, 5-series of 2-deoxystreptamine aminoglycoside antibiotics to resist aminoglycoside modifying enzymes and increase ribosomal target selectivity. ACS Infect. Dis., 2019, 5(10), 1718-1730.
[http://dx.doi.org/10.1021/acsinfecdis.9b00128] [PMID: 31436080]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy