1,2-O-Isopropylidene-3-O-butylglucofuranose-derived Ester, and Ether: Synthesis, Characterization, and Antimicrobial Study (original) (raw)
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Journal of Physical Therapy Science
This work mainly describes the selective synthesis of 6-O-stearoylation of 1,2-O-isopropylidene-α- D-gluco-furanose and subsequent testing of this compound and its derivatives for antimicrobial activity. Bisacetone D-glucose (3) was prepared from D-glucose, which upon selective deprotection of the 5,6-O- isopropylidene group gave 3,5,6-triol (4) in good yield. Unimolecular direct stearoylation of this triol at low temperature provided the desired selective 6-O-stearoate (5) in 64% yield. To further elucidate the structure and to create novel glucofuranose derivatives of biological importance, 3,5-di-O-acetate (6), 3,5-di-O-mesylate (7) and 3,5-di-O-benzoate (8) were also prepared from the stearoate (5). All of the glucofuranoses (3–8) were tested via in-vitro antibacterial and antifungal functionality tests against 10 human pathogenic bacteria and 7 fungi. These experiments revealed that some of the tested glucofuranose derivatives (5, 6 and 8) showed excellent antimicrobial functio...
Journal of the Turkish Chemical Society Section A: Chemistry, 2021
Site selective acylation of monosaccharides and oligosaccharides are very necessary for the preparation of both natural and novel synthetic carbohydrate compounds, synthetic intermediates, postglycosylation modifications, and for the preparation of therapeutic agents including research tools for glycobiology. Hence, site selective octanoylation of 1,2-O-isopropylidene-α-D-glucofuranose was conducted. Under low temperature in anhydrous pyridine direct unimolar octanoylation of this glucofuranose without any catalyst exhibited selectivity at C-6 hydroxyl group. The C-6 O-octanoylglucofuranose, thus obtained, was then used for the preparation of three 3,5-di-O-acyl esters in a similar direct method to get novel esters of glucofuranose. Characterization of all the glucofuranose esters by 1D and 2D spectroscopic technique is also discussed herein.
DFT Based Comparative Studies of Some Glucofuranose and Glucopyranoside Esters and Ethers
Journal of Applied Science & Process Engineering
Carbohydrate-based molecular scaffolding received significant interest due to its impact on the drug discovery and development in synthetic carbohydrate chemistry during the last couple of decades. In this respect, four glucose compounds in the furanose and pyranose forms with ester and ether functionality were selected for their structural, thermodynamic and chemical reactivity studies. PASS predication indicated that the glucose in the six-membered pyranose form was more prone to biological properties compared to their five-membered furanose form. Also, in the pyranose form acetate ester (3) had more potentiality than the ethyl ether (4). The HOMO-LUMO energy gaps were almost similar for both monosubstituted furanose and pyranose glucose indicating their almost similar reactivities. It was also inferred that these 6-O-substituted compounds followed Lipinski’s rule with the acceptable range of ADMET levels, and hence, safe from lethal proarrhythmic risks. Hopefully, these results c...
D-glukoz, iyi bir verimle 1,2:5,6-di-O-izopropiliden-α-D-gluko furanoz (1) dönüştürüldü. Diaseton glikoz (1)'dan 5,6-O-izopropiliden grubunun çıkarılması, mono asetal glikoz (2)'un elde edilmesini sağlayarak, dikkatli bir şekilde hidroliz ile elde edilmiştir. Burada karşılık gelen 3,5,6-triO -asil türevlerinin döşenmiş asile edici bir dizi ajan kullanarak uygun verimle doğrudan 1,2-O-izopropiliden-α-D-gluckofuranoz (2) 'nin seçici asilasyonu rapor edilmektedir. Yeni sentezlenmiş bileşiklerin yapıları FTIR, 1 H-NMR spektroskopisi ve element analizi ile tespit edildi. Sentezlenen tüm bileşikler altı insan patojen bakterisine karşı in vitro antibakteriyel işlevsellik test kimyasalı olarak kullanılmıştır. Değerlendirme çalışması, test kimyasalları iyi antibakteriyel işlevlerine orta derecede tepki verdiğini göstermiştir. Aynı zamanda, test kimyasallarının, Gram-pozitif bakterilere karşı Gramnegatif mikroorganizmalara olduğundan daha etkili olduğu görülmüştür. Anahtar Kelimeler D-Glikoz, asilasyon, spektroskopi, antibakteriyel.
International Journal of Biosciences (IJB), 2013
Some acylated D-glucofuranose (2, 3, 5, 6) and D-glucopyranose (8, 9) derivatives were prepared by direct acylation method for comparative antimicrobial studies. All the compounds (1-9) were screened for in vitro antibacterial activity against ten human pathogenic bacteria and antifungal activity against four pathogenic fungi. The study revealed that the D-glucopyranose derivatives were more prone towards antimicrobial functionality than that of the D-glucofuranose derivatives.
Direct unimolecular lauroylation of 1,2-O-isopropylidene-α-D-gluco-furanose (4) at low temperature provided the desired selective 6-O-lauroate (5) in good yield. For structural elucidation and to get newer glucofuranose derivatives of biological importance 3,5-di-O-acetate (6), 3,5-di-O-mesylate (7) and 3,5-di-O-benzoate (8) were also prepared from lauroate 5. All the glucofuranoses (3-8) were employed as test chemicals for in vitro antibacterial and antifungal functionality test against ten human pathogenic bacteria and seven fungi, respectively. The study revealed that some of the tested glucofuranose derivatives (5,6,8) showed moderate to good antimicrobial functionalities as compared to the standard antibiotics.
Tetrahedron Letters, 1987
Sutnmahy -The phollahy hydRox@ ghOUpb 06 a-c-g&cobe and me&@-a-c-gLucobide WeRe bC!kc.ti-veLy eM&~ied by &eating -the dhee bugakb wLth N-a~~kiazo~~ine-Z-fkion~, thu6 &,(0/zding heApetiv@ 6-f-a@-c-g©nanobeA and mtihyL-6-g-acyl-a-P-gkkcopyhanobideb in high y&&l.&. JhA MW h&XtioVI .i~ compatied wtih au/r phevioUb bynthekb 06 I-a-a@-p-c-g~UCOpyhUVLObeA dhom p-c-g4kcobe and intenpheied in tenmb 06 anomekc e66ect. Esters in the 6 position of mono-and disaccharides are generally obtained according to two main methods. The most important one involves the synthesis of selectively protected intermediates followed by esterification of the remaining free hydroxyl with an acyl chloride, and subsequent removal of the protecting groups. 1 As an illustration of the second method, 6-&acyl-a-D-glucopyranoses were obtained by direct reaction of an acyl chloride with unprotected a-glucose 1 in pyridine solution. 233 In the latter case, the 6-monoesters of type 2 were obtained in low yields (IO-30 %), together with 1,6-, 2,6-diesters and 1,2,6-triesters of glucose. Moreover, the purification of the above monoesters was tedious. More recently, JENKINS4 prepared the 6,6'-dipalmitates of trehalose and saccharose in satisfactory yields (55 % and 36 % yields respectively), by treating the corresponding unprotected sugar with triphenylphosphine, diisopropyl azodicarboxylate and palmitic acid in DMF solution, thus applying in the carbohydrate field the MITSONOBU reaction.5 A recent paper6 describing an enzymatic preparation of monoacylated sugars, prompted us to display our new method for the syntheses of 6-g-acyl-Q-glucopyranoses 4 and methyl-6-g-acyl-a-g-glucopyranosides 5, which is more convenient, in matter of yields, reaction time, temperature and molar ratios of the reactants as well. Thus, a solution of m-g-glucose 1 or methyl-a-Q-glucoside 2 (3 equ.) and N-acylthiazolidine-2-thione A7 (1 equ.) in dry pyridine8 was treated with a catalytic amount of NaH and 4-dimethylaminopyridine. The reaction was carried out at room temperature and was followed by TLC. The yellow colour of the acylating agent 2 gradually disappeared within l-2 hours. The mixture was then extrated according to our usual procedure.' The esters 2 were isolated from mercaptothiazoline 5 by column chromatography on silica-gel and then recrystallizated from acetone. The yields of pure monoester varied from 60 to 88,4 % with regards to the acylating reagent 3 (see table). The monoesters 2 were isolated in theaform or as a mixture of a and p anomers after column chromatography and repeated crystallisation for separating them chromatog. (a) 67 -id-63 -id-66 -id-60 -id-61 -id-88. -id-70 -id-m.p. ("C) 133 -135 134 -135 136 -139 46 -49 63 -66 71 -72 78 -80 86 -91 Solvent for recrystall. AcOEt/hexane -id-EtOH Me2C0 -id--id--id--id-(a) silica gel MERCK 60 H ; elution with CH2C12 followed by Me2CO/CH2C12 50 : 50 V/V and then Me2CO The structures of the esters 2 and 2 were determined by elemental analysis, IR and N M R and comparison with published data. 2,399 The ester group was characterized by a very fine absorption band located near 1730 cm -1 in the IR spectrum, that is, at a frequency lower than for the lp-monoesters we previously obtained 9b,lO or than for the la-monoesters. 3 The 'H-NMR spectrum (DMSO-d6) showed a signal centred neara4,9 ppm (Jl 2 = 3.5 Hz) for compounds 4 and 84.6 ppm (Jl,2 = 3 Hz) for esters 5, characteristic of the animeric 1 proton. And as expected, the triplet neara4.5-4.7 ppm typical of the primary 6-hydroxyl did not show up. In deuterated pyridine, the Hl proton of 5 appeared at S 5.08 ppm (Jl 2= 3 Hz) and the anomerit proton of the esters 2 resonated at 6 5.9 ppm (Jl 2 = 3.5 Hz). iut after three hours at room temperature, another signal appeared at S 5.9 ppm [JI 2 = 7.5 Hz) as the result of the anomerisation of the la -OH into lp-OH,which evidences ihat esterification did not take place at the anomeric hydroxyl of glucose. The esters 4 did not anomerize in DMSO-d6, which made it possible to run their 13 C-NMR spectra in this solvent. The spectra of esters 4 and 5 presented signals respectively at S 63.89 ppm and S 63.53 ppm due to the C6 carbons, that is 3811 deshielded by ca. 3 ppm compared to the corresponding signal in the spectra of l-p-esters of gluc0se.l'
Enzyme and Microbial Technology, 2005
The lipases from Thermomyces lanuginosus (immobilized by granulation with silica) and Candida antarctica B (adsorbed on Lewatit, "Novozym 435") were comparatively assayed for the synthesis of sugar esters by transesterification of sugars with fatty acid vinyl esters in 2-methyl-2-butanol:dimethylsulfoxide mixtures. We found that lipase from C. antarctica B is particularly useful for the preparation of 6,6'-diacylsucrose, whereas T. lanuginosus lipase catalyzes selectively the synthesis of 6-Oacylsucrose. The granulated T. lanuginosus lipase retained more than 80% of its initial activity after 20 cyles of 6 hours. Both lipases were similarly effective for the regioselective synthesis of 6'-O-palmitoylmaltose and 6-O-lauroylglucose. The effect of the synthesized sugar esters on the growth in liquid medium of various microorganisms (Gram-positive, Gram-negative and yeasts) was evaluated. 6-Olauroylsucrose and 6'-O-lauroylmaltose inhibited the growth of Bacillus sp. at a concentration of 0.8 mg/ml, and of Lactobacillus plantarum at 4 mg/ml. Sucrose dilaurates and 6-O-lauroylglucose did not show antimicrobial activity, probably due to their low aqueous solubility. As regards the inhibition of yeasts, none of the tested carbohydrate esters inhibited significantly the growth of Zygosaccharomyces rouxii and Pichia jadinii. Enzyme and Microbial Technology (2005) 36, 391-398 3