17651-11-5Relevant articles and documents
Factors determining the reaction temperature of the solvent-free enzymatic synthesis of trehalose esters
Ogawa, Shigesaburo,Endo,Kitahara,Yamagishi, Takayuki,Aoyagi, Satoka,Hara, Setsuko
, (2019)
Solvent-free synthesis encourages the design of processes and products that reduce the use and generation of hazardous chemicals. Given the importance of developing greener methodologies, we sought to determine the factors influencing the reaction temperature required for solvent-free, enzymatic synthesis of sugar esters such as trehalose (TRE) esters, using Novozyme 435 as the enzyme catalyst. The use of lauric acid (La) and ethyl laurate (LaEt) as acyl donors did not affect the activation temperature for the generation of trehalose diesters (TDEs), despite the differences in corresponding by-products (water and ethanol). However, when glucose (GLU) and La were employed as reaction substrates as a comparison, glucose monoester (GME) generation readily occurred at much lower temperatures than with the TRE esters, even without a water collection device. Moreover, when the glass transition temperature (Tg) of the sugar substrates increased, a higher reaction temperature was required. These results suggest that while the activation temperature of the reaction did not correlate with the boiling point of the by-product, it did correlate with the glass transition temperature (Tg) of the trehalose substrates. Thus, our work demonstrates the importance of the physical state of amorphous matrices in determining the optimal reaction temperature of a solvent-free sugar synthesis.
Solubility of glucose in mixtures containing 2-methyl-2-butanol, dimethyl sulfoxide, acids, esters, and water
, p. 807 - 810 (2002)
Solubility measurements of glucose in a variety of binary, ternary, and multicomponent mixtures containing 2-methyl-2-butanol, dimethyl sulfoxide, acids, esters, and water at different temperatures are presented. The solubilities of crystalline β-glucose,
Tetraalkylammonium Ionic Liquids as Dual Solvents–Catalysts for Direct Synthesis of Sugar Fatty Acid Esters
Lin, Xiao-Sheng,Zou, Yong,Zhao, Kai-Hua,Yang, Tao-Xiang,Halling, Peter,Yang, Zhen
, p. 511 - 517 (2016)
As nonionic surfactants derived from naturally renewable resources such as sugars and fatty acids, sugar fatty acid esters have been widely utilized in food, cosmetic and pharmaceutical industries. Our present study has demonstrated that the inexpensive and halogen-free tetraalkylammonium salts (e.g., [Bu4N][Ac], [Et4N][Ac] and [Me4N][Ac]) can act as dual solvents–catalysts for regioselective acylation to produce glucose laurate. This non-enzymatic synthesis can proceed under mild conditions with high specificity, and the conversions obtained were superior to that when an enzyme catalyst (lipase, EC 3.1.1.3) was added. A higher yield was obtained in the ammonium salt with a longer alkyl chain on the cation, while no product was obtained in [Bu4N][HSO4] and [Bu4P][Ac]. A reaction mechanism has been proposed, which is supported by phase-transfer catalysis and law of matching water affinity.
Retarding activity of 6-O-Acyl-D-alloses against plant growth
Kobayashi, Miyuki,Ueda, Mariko,Furumoto, Toshio,Kawanami, Yasuhiro
, p. 216 - 217 (2010)
The retarding activity of 6-O-dodecanoyl-D-allose against rice growth was higher than that of the octanoate and the decanoate. The activities of 6-O-dodecanoyl-D-glucose,-D-mannose, and-D-galactose against rice seedlings were examined. 6-O-Dodecanoyl-D-allose exhibited the highest activity, suggesting the importance of the a-axial hydroxy group at C-3 of D-allose.
One-step synthesis of carbohydrate esters as antibacterial and antifungal agents
AlFindee, Madher N.,Zhang, Qian,Subedi, Yagya Prasad,Shrestha, Jaya P.,Kawasaki, Yukie,Grilley, Michelle,Takemoto, Jon Y.,Chang, Cheng-Wei Tom
, p. 765 - 774 (2018)
Carbohydrate esters are biodegradable, and the degraded adducts are naturally occurring carbohydrates and fatty acids which are environmentally friendly and non-toxic to human. A simple one-step regioselective acylation of mono-carbohydrates has been developed that leads to the synthesis of a wide range of carbohydrate esters. Screening of these acylated carbohydrates revealed that several compounds were active against a panel of bacteria and fungi, including Staphylococcus aureus, methicillin-resistant S. aureus (MRSA), Candida albicans, Cryptococcus neoformans, Aspergillus flavus and Fusarium graminearum. Unlike prior studies on carbohydrate esters that focus only on antibacterial applications, our compounds are found to be active against both bacteria and fungi. Furthermore, the synthetic methodology is suitable to scale-up production for a variety of acylated carbohydrates. The identified lead compound, MAN014, can be used as an antimicrobial in applications such as food processing and preservation and for treatment of bacterial and fungal diseases in animals and plants.
Highly efficient synthesis of glucose fatty acid esters catalyzed by high performance lipase preparations
Arora, Benu
, p. 2489 - 2497 (2021/09/28)
Glucose fatty acid esters were synthesized using cross-linked enzyme aggregates (CLEAs), protein coated microcrystals (PCMCs) and cross-linked protein coated microcrystals (CLPCMCs) of Candida antarctica lipase B (CALB) as biocatalyst designs in single and mixed solvent systems. Up to 90% conversion and more than 99% regioselectivity were obtained using vinyl acetate as the acyl donor in a solvent system composed of 2-methyl-2-butanol (2M2B) and 30% (v/v) DMSO, with CALB CLEAs within 45 min. Similar results were obtained with CALB CLPCMCs as the biocatalyst under the same reaction conditions. This approach was then extended to the synthesis of glucose esters with higher acyl chain length. The synthetic strategy used in this work can potentially be extended for the fast and regioselective esterification/transesterification of other sugars as well.
Enzymatic Preparation of a Homologous Series of Long-Chain 6- O -Acylglucose Esters and Their Evaluation as Emulsifiers
Liang, Min-Yi,Chen, Yongsheng,Banwell, Martin G.,Wang, Yong,Lan, Ping
, p. 3949 - 3956 (2018/04/23)
Sugar fatty acid esters are nonionic surfactants that are widely exploited in the food and cosmetics industries, as well as in the oral care and medical supply fields. Accordingly, new methods for their selective synthesis and the tuning of their emulsifying properties are of considerable interest. Herein we report simple and irreversible enzymatic esterifications of d-glucose with seven fatty acid vinyl esters. The foaming and emulsifying effects of the resulting 6-O-acylglucose esters were then evaluated. In accord with expectations, when the length of the alkyl side chain associated with the 6-O-acylglucose esters increases, then their hydrophilic-lipophilic balance (HLB) values decrease, while the stabilities of the derived emulsions improve. In order to maintain good foaming properties, alkyl side chains of at least 9 to 11 carbons in length are required. In the first such assays on 6-O-acylglucose esters, most of those described herein are shown to be nontoxic to the HepG2, MCF-7, LNacp, SW549, and LO-2 cell lines.
