One-step synthesis of carbohydrate esters as antibacterial and antifungal agents

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

“…Finally, although some of the sugar-based esters here presented have already been published for other applications and also as possible antibacterial agents [22][23][24][29][30][31][32][33], a detailed comparative study concerning the properties of a relative large number of both aliphatic and aromatic amphiphilic carbohydrate esters as antimicrobial (Gram-positive, Gram-negative, and fungi) and mostly antibiofilm agents is still lacking.…”

“…Purification of the residue by flash chromatography (EtOAc/cyclohexane 8:2) gave 7a-e as white spongy solids and 8a-e as white crystal solids. (Scheme 2).6-O-Octanoyl-d-mannopyranose (mannose caprylate, URB1389) (7a)[29] Yield = 57%, α/β = 1:0.5. 1 H NMR (400 MHz, DMSO): δ = 0.86 (t, 3H+1.5H, J = 6.5 Hz, CH 3 ), 1.24-1.26 (m, 8H+4H), 1.50-1.53 (m, 2H+1H, OCCH 2 CH 2 ), 2.26-2.31 (m, 2H+1H, OCCH 2 CH 2 ), 3.21-3.33 (m, 1.5H, H 3β , H 4β , H 5β ), 3.35-3.41 (m, 1H, H 4α ), 3.49-3.55 (m, 2H+0.5H, H 2α , H 3α , H 2β ), 3.70 (ddd, 1H, J H5α-H6bα = 1.5 Hz, J H5α-H6aα = 7.0 Hz, J H5α-H4α = 9.0 Hz, H 5α ), 3.94-4.02 (m, 1H+0.5H, H 6aα , H 6aβ ), 4.27-4.32 (m, 1H+0.5H, H 6bα , H 6bβ ), 4.53-4.59 (m, 1H+1H, OH 2α , H 1β , OH 2β ), 4.63 (d, 1H, J OH3α-H3α = 4.0 Hz, OH 3α ), 4.66 (d, 0.5H, J OH3β-H3β = 5.5 Hz, OH 3β ), 4.86 (dd, 1H, J H1α-H2αJ H1α-OH1α = 4.5 Hz, H 1α ), 4.89 (d, 1H, J OH4α-H4α = 5.5 Hz, OH 4α ), 4.94 (d, 0.5H, J OH4β-H4β = 5.0 Hz, OH 4β ), 6.26 (d, 0.5H, J OH1β-H1β = 8.5 Hz, OH 1β ), 6.38 (d, 1H, J OH1α-H1α = 4.5 Hz, OH 1α ) ppm.…”

Surface‐Active Properties and Anti‐Microbial Activities of Esterified Maltodextrins

“…However, the anti‐microbial mechanisms of mono‐, di‐, oligosaccharide ester have not been investigated clearly. AlFindee et al reported that mannose myristate exerted its bioactivity via pore formation of the cell membrane of E. coli and S. aureus . The results reported by Zhoa et al also confirmed that sugar fatty acid esters can disrupt the cell membrane of bacteria based on observation under an electron microscope.…”

“…On the other hand, Hathcox and Beuchat observed that the growth of E. coli was unaffected in tryptic soy broth containing 1 mg mL −1 of a commercial sucrose laurate. AlFindee et al reported that among eight mannose esters with carbon chains from 2, 4, 6, 8, 10, 12, 14, and 16, the mannose ester with myristic acid (C‐14) (MANO14) was the most active compound with the lowest minimum inhibitory concentration (MIC) against S. aureus and E. coli and also showed broad ‐ spectrum activity against bacteria and fungi while having relatively low cytotoxicity toward animal cells. Ferrer et al and Zhao et al reported that disaccharide monoesters exhibited better anti‐microbial activity than monosaccharide monoesters.…”

In Situ Carbonylative Synthesis of Aromatic Esters and Formation of Quinazoline‐2,4(1H,3H)‐diones by Chemical Fixation of CO2 in Assistance of Polymer‐Supported Palladium Catalyst

“…Phenyl acetylsalicylate which is an aromatic ester is used as an anti‐inflammatory drug. Also some esters are used as an antiseptic and antibacterial agent . Aromatic esters are also used in many steps of organic synthesis as a building block.…”