- Parallel anti-sense two-step cascade for alcohol amination leading to ω-amino fatty acids and α,ω-diamines
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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.
- Sung, Sihyong,Jeon, Hyunwoo,Sarak, Sharad,Ahsan, Md Murshidul,Patil, Mahesh D.,Kroutil, Wolfgang,Kim, Byung-Gee,Yun, Hyungdon
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supporting information
p. 4591 - 4595
(2018/10/23)
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- Diamines for Polymer Materials via Direct Amination of Lipid- and Lignocellulose-based Alcohols with NH3
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Via an all-catalytic route, long-chain diamines were prepared by the catalytic direct amination of long-chain diols, derived from plant oils. High conversion was achieved with good selectivity, with the amount of nitrile impurities formed suppressed to a low level. From the lignocellulose-based 5-hydroxymethylfurfural (5-HMF), or from bis(hydroxymethyl)furan, 2,5-bis(aminomethyl)furan (BAMF) was generated. 5-HMF was converted in a one-pot, one-step direct amination and reductive amination using ammonia. In both cases, the reaction proceeded very efficiently. In the combined amination and reductive amination, the H2 concentration is a rate-limiting factor. Reducing the partial pressure of H2 also shortened the reaction time required significantly. Polycondensation of the long-chain diamines with long-chain diacids led to higher molecular weight polyamides, illustrating the quality of the diamines obtained by this synthetic approach as monomers.
- Pingen, Dennis,Schwaderer, Judith B.,Walter, Justus,Wen, Jiaqi,Murray, George,Vogt, Dieter,Mecking, Stefan
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p. 3027 - 3033
(2018/05/29)
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