72138-85-3Relevant academic research and scientific papers
Simple preparation method of alkyl maltoside surfactant
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Paragraph 0030; 0032, (2020/06/09)
The invention belongs to the technical field of fine chemicals, and specifically discloses a preparation method of sugar-based nonionic surfactant alkyl-beta-D-maltoside. The preparation method includes the steps of performing an acylation reaction on maltose to obtain octa-O-acetyl-D-maltose, performing condensation on the octa-O-acetyl-D-maltose and fatty alcohol, and performing deprotection toobtain the alkyl-beta-D-maltoside. The preparation method provided by the invention is simple and easy to implement, has the advantages of mild and controllable conditions, low costs, and practicability.
Solution Properties of Alkyl β-D-Maltosides
Li, Zhencao,Chen, Guoyong,Chen, Langqiu,Zhang, Yanhua,Dai, Zhiyong
, p. 731 - 742 (2019/04/10)
Alkyl β-D-maltosides are an important class of sugar-based nonionic surfactants and have been widely studied. Nevertheless, it is still necessary to investigate further their amphiphilic structure-surface property relationships. In this article, we reported a series of properties of synthetic alkyl β-D-maltosides (6a–6i, n = 6–18) including their hydrophilic–lipophilic balance (HLB) number, water solubility, hygroscopicity, moisture-retention capacity, foaming ability, surface tension, thermotropic phase behavior, and skin irritation. Their HLB number and water solubility decreased with increasing alkyl chain length. Hexyl β-D-maltoside exhibited the strongest hygroscopicity and moisture-retention capacity. Decyl β-D-maltoside and dodecyl β-D-maltoside possessed excellent foaming power and foaming stability. Furthermore, the critical micelle concentration (CMC) of alkyl β-D-maltoside (6a–6g, n = 6–14) and their surface tension at CMC decreased with increasing alkyl chain length. At last, alkyl β-D-maltosides (6a–6g) should be considered as safe surfactants by the skin irritation assessment.
Synthesis of uniformly deuterated n-dodecyl-β -d-maltoside (d39 -DDM) for solubilization of membrane proteins in TROSY NMR experiments
Hiruma-Shimizu, Kazumi,Kalverda, Arnout P.,Henderson, Peter J. F.,Homans, Steve W.,Patching, Simon G.
, p. 737 - 743 (2015/02/19)
This work reports the first synthesis of uniformly deuterated n-dodecyl-β -D-maltoside (d39-DDM). DDM is a mild non-ionic detergent often used in the extraction and purification of membrane proteins and for solubilizing them in experimental studies of their structure, dynamics and binding of ligands. We required d39-DDM for solubilizing large α-helical membrane proteins in samples for [15N-1H]TROSY (transverse relaxation-optimized spectroscopy) NMR experiments to achieve the highest sensitivity and best resolved spectra possible. Our synthesis of d39-DDM used d7-D-glucose and d25-n-dodecanol to introduce deuterium labelling into both the maltoside and dodecyl moieties, respectively. Two glucose molecules, one converted to a glycosyl acceptor with a free C4 hydroxyl group and one converted to a glycosyl donor substituted at C1 with a bromine in the α-configuration, were coupled together with an α(1 → 4) glycosidic bond to give maltose, which was then coupled with n-dodecanol by its substitution of a C1 bromine in the α-configuration to give DDM. 1H NMR spectra were used to confirm a high level of deuteration in the synthesized d39-DDM and to demonstrate its use in eliminating interfering signals from TROSY NMR spectra of a 52-kDa sugar transport protein solubilized in DDM.
Specific maltose derivatives modulate the swarming motility of nonswarming mutant and inhibit bacterial adhesion and biofilm formation by pseudomonas aeruginosa
Shetye, Gauri S.,Singh, Nischal,Jia, Changqing,Nguyen, Chan D.K.,Wang, Guirong,Luk, Yan-Yeung
, p. 1514 - 1523 (2014/07/21)
We have demonstrated that specific synthetic maltose derivatives activate the swarming motility of a Pseudomonas aeruginosa nonswarming mutant (rhlA) at low concentration, but inhibit it at high concentration. Although these molecules are not microbicidal, active maltose derivatives with bulky hydrocarbon groups inhibited bacterial adhesion, and exhibited biofilm inhibition and dispersion (IC50 ～20 μM and DC50 ～30 μM, respectively). Because the swarming motility of the rhlA mutant is abolished by the lack natural rhamnolipids, the swarming activation suggests that maltose derivatives are analogues of rhamnolipids. Together, these results suggest a new approach of controlling multiple bacterial activities (bacterial adhesion, biofilm formation, and swarming motility) by a set of disaccharide-based molecules.
Synthesis of C7-C16-Alkyl maltosides in the presence of tin(IV) chloride as a lewis acid catalyst
Markovic, Zoran,Predojevic, Jasmina,Manojlovic, Nedeljko T.
experimental part, p. 83 - 90 (2012/05/20)
The synthesis of C7- to C16-alkyl maltosides in the presence of tin(IV) chloride as Lewis acid catalyst was performed. The characterization of the products and theoretical investigation of the crucial step in the synthesis were carried out. The preparation of the β-maltosides required reaction time of 1 h, and that of the α-maltosides was 72 h. The side products were the α-D-maltosidechloride and 2-hydroxy-β-maltoside, respectively. The PM3 calculation confirmed the formation of the kinetically controlled β-product.
Cyclomaltodextrin glucanotransferase-catalyzed transglycosylation from dextrin to alkanol maltosides
Zhao, Haisuo,Naito, Hiroyuki,Ueda, Yoshimi,Okada, Katsuhide,Sadagane, Kenji,Izumi, Minoru,Nakajima, Shuhei,Baba, Naomichi
scheme or table, p. 3006 - 3010 (2009/04/07)
Maltosides of butanol, octanol, and lauryl alcohol were found for the first time to serve as substrates for cyclomaltodextrin glucanotransferase (CGTase), and glycosyl residue was transfered from dextrin to the substrate affording novel maltosides with 3-
Simple preparations of alkyl and cycloalkyl α-glycosides of maltose, cellobiose, and lactose
Koto, Shinkiti,Hirooka, Motoko,Tashiro, Takako,Sakashita, Motokazu,Hatachi, Masaharu,Kono, Takayuki,Shimizu, Miho,Yoshida, Nahoko,Kurasawa, Sayaka,Sakuma, Natsuko,Sawazaki, Sunao,Takeuchi, Akihiro,Shoya, Naomi,Nakamura, Emi
, p. 2415 - 2424 (2007/10/03)
Alkyl, cycloalkyl, allyl, 4-pentenyl, and benzyl α-glycosides of maltose, cellobiose, and lactose were prepared via direct reaction of the free bioses with a binary AcBr-AcOH system, followed by glycosidation with alcohol using FeCl3 in MeNO2 or CH2Cl2, Zemple?n deacetylation, and the chromatographic resolution of the mixture. The respective β-biosides were obtained via the glycosidation in MeCN. Alkyl, cycloalkyl, allyl, 4-pentenyl, and benzyl α-glycosides of maltose, cellobiose, and lactose were prepared (17-77% yield; α/β = 70/30-96/4) via a direct reaction of the free disaccharides with a binary AcBr-AcOH mixture, followed by glycosidation with alcohol using FeCl3 in MeNO2 or CH2Cl2, Zemple?n deacetylation, and resolution of the anomeric mixture of glycosides by chromatography. Using MeCN as solvent for the glycosidation step, the corresponding β-biosides were also prepared (16-61% yield; α/β = 25/75-5/95).
