53005-24-6Relevant articles and documents
Parallel anti-sense two-step cascade for alcohol amination leading to ω-amino fatty acids and α,ω-diamines
Sung, Sihyong,Jeon, Hyunwoo,Sarak, Sharad,Ahsan, Md Murshidul,Patil, Mahesh D.,Kroutil, Wolfgang,Kim, Byung-Gee,Yun, Hyungdon
supporting information, p. 4591 - 4595 (2018/10/23)
Running two two-step cascades in parallel anti-sense to transform an alcohol to an amine allowed the conversion of ω-hydroxy fatty acids (ω-HFAs) and α,ω-diols to the corresponding ω-amino fatty acids (ω-AmFAs) and α,ω-diamines, respectively. The network required only two enzymes namely an aldehyde reductase (AHR) and a transaminase (TA). Benzylamine served on the one hand as amine donor and on the other hand after deamination to benzaldehyde also as oxidant. All ω-HFAs tested were efficiently transformed to their corresponding ω-AmFAs using purified enzymes as well as a whole-cell system, separately expressing both the enzymes, with conversions ranging from 80-95%. Additionally, a single-cell co-expressing all enzymes successfully produced the ω-AmFAs as well as the α,ω-diamines with >90% yield. This system was extended by employing a lactonase, enabling the transformation of ?-caprolactone to its corresponding ω-AmFA with >80% conversion.
Cross-metathesis approach to produce precursors of nylon 12 and nylon 13 from microalgae
Ameh Abel, Godwin,Oliver Nguyen, Kim,Viamajala, Sridhar,Varanasi, Sasidhar,Yamamoto, Kana
, p. 55622 - 55628 (2015/02/02)
A two-step synthesis for producing methyl 12-aminododecanoate and 13-aminotridecanoate, the precursors of nylon 12 and nylon 13, from methyl oleate is described. First, methyl 11-cyano-9-undecenoate or 12-cyano-9-dodecenoate were prepared by cross metathesis of methyl oleate with either allyl cyanide or homoallyl cyanide, respectively. Subsequently, all the unsaturation of the two intermediates was hydrogenated to deliver the final products. This method represents the first synthesis of nylon 12 and 13 precursors from methyl oleate, an ester of an abundant and renewable natural fatty acid present in vegetable oil or microalgae. It also represents the shortest synthesis of nylon precursors from fatty acids, and as demonstrated in this study, can be directly applied to crude fatty acid methyl ester extracts from microalgae.
Direct terminal alkylamino-functionalization via multistep biocatalysis in one recombinant whole-cell catalyst
Schrewe, Manfred,Ladkau, Nadine,Buehler, Bruno,Schmid, Andreas
supporting information, p. 1693 - 1697 (2013/07/19)
Direct and regiospecific amino-functionalization of non-activated carbon could be achieved using one recombinant microbial catalyst. The presented proof of concept shows that heterologous pathway engineering allowed the construction of a whole-cell biocatalyst catalyzing the terminal amino-functionalization of fatty acid methyl esters (e.g., dodecanoic acid methyl ester) and alkanes (e.g., octane). By coupling oxygenase and transaminase catalysis in vivo, both substrates are converted with absolute regiospecificity to the terminal amine via two sequential oxidation reactions followed by an amination step. Such demanding chemical three-step reactions achieved with a single catalyst demonstrate the tremendous potential of whole-cell biocatalysts for the production of industrially relevant building blocks. Copyright
Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis
Miao,Fischmeister,Dixneuf,Bruneau,Dubois,Couturier
, p. 2179 - 2183 (2012/09/22)
The ruthenium-catalyzed cross-metathesis of the unsaturated fatty acid derivative 10-undecenenitrile 1 arising from castor oil with methyl acrylate produces a C12 nitrile ester with high turnover number. This product has potential as a new bio-sourced intermediate for the production of polyamides. This route competes favourably with the reverse cross-metathesis of methyl 10-undecenoate with acrylonitrile leading to the same C12 α,ω-amino ester 7 after hydrogenation of the carbon-carbon double bond and the nitrile functionality.
Tandem catalytic acrylonitrile cross-metathesis and hydrogenation of nitriles with ruthenium catalysts: Direct access to linear α,ω- aminoesters from renewables
Miao, Xiaowei,Fischmeister, Cédric,Bruneau, Christian,Dixneuf, Pierre H.,Dubois, Jean-Luc,Couturier, Jean-Luc
scheme or table, p. 1410 - 1414 (2012/10/08)
Fraternité, Solidarité & complémentarité en Catalyse: Tandem alkene cross-metathesis of acrylonitrile with long-chain alkene and hydrogenation catalysis is performed by using a single ruthenium-alkylidene catalyst precursor. The protocol allows the catalytic transformation of unsaturated fatty acids, derivatives of plant oils, into α,ω-aminoesters. A key step involves the reduction of nitrile-ester intermediates into aminoesters, the precursors of polyamides, with alkene metathesis catalyst residue under mild conditions. Copyright
