Enzymatic chemoselective synthesis of secondary-amide surfactant from N-methylethanol amine

Sharma, J. N.; Batovska, Daniela; Kuwamori, Yuko; Asano, Yasuhisa

doi:10.1263/jbb.100.662

Cited by 17 publications

(8 citation statements)

References 22 publications

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“…The thermostable lipase B from Candida antartica (CAL-B) has proven to be the most effective biocatalyst for aminolysis reactions in organic solvents . Numerous studies of enzymatic aminolysis have been performed by Gotor, Sheldon, and other groups. − Improving the lipase catalytic activity and selectivity can be made by changing the solvent, or the acyl donor, or both. The lipase-catalyzed resolution of racemic amines is reputedly successful in organic solvent of low polarity .…”

Section: Resultsmentioning

confidence: 99%

Highly Selective Enzymatic Kinetic Resolution of Primary Amines at 80 °C: A Comparative Study of Carboxylic Acids and Their Ethyl Esters as Acyl Donors

et al. 2007

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Optimization of the kinetic resolution of 2-amino-4-phenyl-butane was achieved at 80 degrees C using CAL-B-catalyzed aminolysis of carboxylic acids and their ethyl esters. The reactions carried out with long chain esters and the corresponding acids as acyl donors proceeded with remarkably high enantioselectivity. The use of carboxylic acids as acylating agents led to a marked acceleration of the reaction rate compared to their ester counterparts. Lauric acid led to enantiomeric excesses superior to 99.5% for both the remaining amine and the corresponding lauramide at 50% conversion (reached in 3 h). These optimized conditions were applied to the resolution of a series of aliphatic and benzylic amines.

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Section: Resultsmentioning

confidence: 99%

Highly Selective Enzymatic Kinetic Resolution of Primary Amines at 80 °C: A Comparative Study of Carboxylic Acids and Their Ethyl Esters as Acyl Donors

et al. 2007

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“…The obtained compounds are characterized by different attachment points between the chromophore or the sugar and the linker. The presence of the amido bond could permit a novel synthetic pathway to GADs, for example, by using enzymes [14] for the condensation reaction. Detailed analysis of the stability and tinctorial properties of the third generation of GADs are currently under investigation, the results of which will be published in due course.…”

Section: Discussionmentioning

confidence: 99%

A New Generation of Glycoconjugated Azo Dyes Based on Aminosugars

Guazzelli

Catelani

D’Andrea

2015

International Journal of Carbohydrate Chemistry

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The third generation of glycoconjugated azo dyes (GADs) was prepared linking monoazo dyes to 6-amino-6-deoxy-d-galactose or 6′amino-6′-deoxylactose through mixed amido-ester connections. The complementary conjugation reactions were studied using the succinyl derivative of either the acetal protected aminosugar or the azo dye. Target “naturalized” GADs were obtained after acid hydrolysis of the acetal protecting groups present on the sugar moiety.

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“…53 In acetonitrile, at 50˚C for 16 h the presence of 50 mM of the ester and 150 mM of the amine, a high yield (97.3%) was obtained. With another reaction mixture under a different set of conditions (50 mM ester and 200 mM amine; 60˚C for 5 h), a yield of 95.8% was obtained.…”

Section: Synthesis Of Fatty Acid Amidesmentioning

confidence: 98%

Production of Surface Active Compounds by Biocatalyst Technology

Zinjarde

Ghosh

2010

Advances in Experimental Medicine and Biology

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In the current scenario, there is immense concern regarding the environmental issues. Eco-friendly surfactants are becoming a preferred choice for specific applications in spite of their possibly inferior performance or more expensive nature than conventional ones. This chapter deals with the use of enzymes in non-aqueous media for the synthesis of surfactants such as monoglycerides, sugar fatty acid esters, fatty acid amides, alkyl glycosides and lysophospholipids. The conventional methods of synthesizing these classes of surfactants, the variety of enzymes involved, process parameters, yields, advantages and disadvantages have been discussed in detail.

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Enzymatic chemoselective synthesis of secondary-amide surfactant from N-methylethanol amine

Cited by 17 publications

References 22 publications

Highly Selective Enzymatic Kinetic Resolution of Primary Amines at 80 °C: A Comparative Study of Carboxylic Acids and Their Ethyl Esters as Acyl Donors

Highly Selective Enzymatic Kinetic Resolution of Primary Amines at 80 °C: A Comparative Study of Carboxylic Acids and Their Ethyl Esters as Acyl Donors

A New Generation of Glycoconjugated Azo Dyes Based on Aminosugars

Production of Surface Active Compounds by Biocatalyst Technology

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