L-tert-leucine is a non-polar amino acid whose tert-butyl team has significant hydrophobicity as well as steric hindrance, which can well manage the molecular conformation in chain reactions and also develop chiral substances. For that reason, L-tert-leucine is commonly made use of as an inducer or design template in uneven synthesis.Additionally, L-tert-leucine is an important additive in the food and also cosmetic markets.
In the early studies, chemical preparation of L-tert-leucine has problems such as low stereoselectivity, large pollution, complicated process and low yield. At present, the enzymatic method has gradually replaced the chemical method. Several previous studies on the production of L-tert-leucine using hydrolases, acyltransferases and amino acid dehydrogenases] have been reported. Among them, the use of NADH-dependent L-leucine dehydrogenase (LeuDH, EC 18.104.22.168) to prepare L-tert-leucine has the most industrial potential. NAD+-dependent formate dehydrogenase (FDH, EC 22.214.171.124) converts formate to CO2 while producing NADH. Therefore, FDH is usually used in coenzyme regeneration systems. Among all FDHs from different sources, FDH from Candida boidinii (Cb FDH) has been widely used for regeneration of NADH and has been demonstrated on a technical scale. At present, the coupling of LeuDH and Cb FDH to form a coenzyme regeneration system to prepare L-tert-leucine is the focus of research. This method enables continuous regeneration of NAD+ and reduces costs, and Degussa has successfully applied the LeuDH and FDH coupling system to produce L-tert-leucine on a large scale. In a previous study, we identified a novel LeuDH from the halophilic thermophile Laceyella sacchari (Ls LeuDH). Ls LeuDH showed good thermal stability and great potential to synthesize L-tert-leucine in preliminary studies. Therefore, in this paper, we constructed a recombinant E. coli strain for co-expression of Ls LeuDH and Cb FDH, forming a two-enzyme system for the conversion of TMP to L-tert-leucine.
≥300 °C (lit.)
6.3 º (c=4, 6 N HCl 200 ºC)
-9 ° (C=3, H2O)
Keep in dark place,Sealed in dry,Room Temperature
1 M HCl: 50 mg/mL
White to almost white
[α]20/D 9.5°, c = 3 in H2O
125.5 g/L (20 ºC)
L-tert-leucine can be used as a catalyst for the enantioselective oxidative coupling and cyclization of hydroquinones to oxahelixene.
L-tert-leucine is made use of as a nutritional fortifier, pet feed additive, and also used in the synthesis of medicines.
L-tert-leucine utilized as an amino acid is the basic element of healthy protein, and also among its main physiological functions is as a resources for protein synthesis. Occurs in the totally free or bound state in vivo. Proteins in the body are broken down to generate the following amino acids: Alanine, Arginine, Aspartic Acid, Asparagine, Cysteine, Lysine, Methionine, Phenylalanine, Serine, Threonine, Chromine Amino acid, tyrosine, valine.
Production Method of L-tert-leucine
Unnatural amino acids and their derivatives are important chemical intermediates. Among them, L-tert-leucine is an important unnatural amino acid. It can be used for synthesizing pharmaceutical intermediates, as a chiral inducer for asymmetric synthesis and a resolving reagent for asymmetric resolution, and is a chiral precursor for synthesizing a variety of anti-AIDS drugs and hepatitis virus inhibitors. With the development of my country’s social economy and the enhancement of environmental protection awareness, the pharmaceutical and chemical industry not only needs to improve the production capacity of L-tert-leucine, but also needs to create a green and pollution-free production process. Therefore, the use of enzymatic biotransformation to produce L-tert-leucine is being paid more and more attention by relevant institutions. Divided from the production route, the methods for producing L-tert-leucine mainly include chemical reagent separation method, chiral source synthesis method, chemical synthesis method and biotransformation method. Among them, the resolution method is limited by the yield, the chiral source method is limited by the production capacity of natural products, and the cost of chemical synthesis method is high, so other synthetic methods have no successful large-scale application examples. The main method of leucine. In biotransformation method, utilize lipase to split racemate DL-tertiary leucine relevant technological research is more, such as Chinese patent CN201010210770.0 etc., but this route has the same defect as chemical splitting method, namely receive. rate cannot exceed 50%. Therefore, the main research directions of biological methods are currently focused on the route of reducing trimethylpyruvate to L-tert-leucine using L-leucine dehydrogenase, and using formate dehydrogenase to regenerate coenzyme NADH in situ, Ammonium formate is used to provide ammonia molecules and hydrogen atoms. As early as the 1990s, Germany’s Degussa Company used this route to combine with an ultrafiltration membrane reactor to produce L-tertiary leucine. Several patent applications have been disclosed for this route, such as Chinese patents CN201110116253.1, CN201110277030.3, etc. The main problems of its existence are as follows: 1. In fact, the L-tert-leucine dehydrogenase recognized by the academic community will be significantly inhibited by the substrate when the substrate concentration is too high, and the reaction rate will drop sharply (Enzyme Catalysis in Organic Synthesis EditionI, Wiley, 1186). ( J. Mol. Catal: B 1998, 5: 1-11). It can be seen that the above patent The method is inefficient or difficult to repeat. 2. Enzyme feeding amount is too much. Obviously, this is an inevitable consequence of problem I. For example, in the patent CN201110116253.1, the expensive coenzyme NAD feeding amount reaches 1% (w/w) of the substrate, and the economy is poor, and the concentration that the whole cell catalyst accounts for the reaction system is 80% (4g/5 mL) in the patent CN201110277030.3 3. There is no clear post-extraction process. Also due to the existence of problem I, its yield and yield cannot meet the needs of industrialized production. Based on the above three points, there is no report on the large-scale production of L-tert-leucine using this method. In order to solve the above issues, the item of the present creation is to offer a technique for enzymatically manufacturing L-tert-leucine. The technique has light preparation problems, is eco-friendly, has high return and also affordable, and also appropriates for commercial production. In order to attain the above purpose, the technical plan provided by the innovation is: a production approach of L-tertiary leucine, the technique makes use of L-leucine dehydrogenase as well as formate dehydrogenase to produce L-tertiary leucine, Its preparation response formula is:
a production approach of L-tertiary leucine, the technique makes use of L-leucine dehydrogenase as well as formate dehydrogenase to produce L-tertiary leucine, Its preparation response formula is: Wherein, LeuDH is leucine dehydrogenase; NADH is minimized nicotinamide adenine dinucleotide, particularly reductase coenzyme; NAD is oxidized nicotinamide adenine dinucleotide, particularly dehydrogenase coenzyme; FDH is formate dehydrogenase.
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