scholarly journals A bicyclic S-adenosylmethionine regeneration system applicable with different nucleosides or nucleotides as cofactor building blocks

2021 ◽  
Author(s):  
Désirée Popadić ◽  
Dipali Mhaindarkar ◽  
Mike H. N. Dang Thai ◽  
Helen C. Hailes ◽  
Silja Mordhorst ◽  
...  
Keyword(s):  
Building Blocks ◽  
Regeneration System ◽  
Methyl Donor ◽  
By Products

The polyphosphate-driven bicyclic S-adenosylmethionine (SAM) regeneration system uses S-methylmethionine as a ‘2-in-1’ methyl donor without producing by-products and can be run with SAM nucleobase analogues such as S-cytidyl- and S-inosylmethionine.

scholarly journals Wine By-Products as Raw Materials for the Production of Biopolymers and of Natural Reinforcing Fillers: A Critical Review

Polymers ◽  
2021 ◽  
Vol 13 (3) ◽  
pp. 381
Author(s):  
Alessandro Nanni ◽  
Mariafederica Parisi ◽  
Martino Colonna
Keyword(s):  
Critical Review ◽  
Raw Materials ◽  
Green Revolution ◽  
Building Blocks ◽  
Poly Lactic Acid ◽  
Butylene Succinate ◽  
Reinforcing Fillers ◽  
Plastic Industry ◽  
Review Reports ◽  
By Products

The plastic industry is today facing a green revolution; however, biopolymers, produced in low amounts, expensive, and food competitive do not represent an efficient solution. The use of wine waste as second-generation feedstock for the synthesis of polymer building blocks or as reinforcing fillers could represent a solution to reduce biopolymer costs and to boost the biopolymer presence in the market. The present critical review reports the state of the art of the scientific studies concerning the use of wine by-products as substrate for the synthesis of polymer building blocks and as reinforcing fillers for polymers. The review has been mainly focused on the most used bio-based and biodegradable polymers present in the market (i.e., poly(lactic acid), poly(butylene succinate), and poly(hydroxyalkanoates)). The results present in the literature have been reviewed and elaborated in order to suggest new possibilities of development based on the chemical and physical characteristics of wine by-products.

scholarly journals Lipase Catalyzed Synthesis of Enantiopure Precursors and Derivatives for β-Blockers Practolol, Pindolol and Carteolol

Catalysts ◽  
2021 ◽  
Vol 11 (4) ◽  
pp. 503
Author(s):  
Morten Gundersen ◽  
Guro Austli ◽  
Sigrid Løvland ◽  
Mari Hansen ◽  
Mari Rødseth ◽  
...  
Keyword(s):  
Building Block ◽  
Kinetic Resolution ◽  
Enantiomeric Excess ◽  
Catalytic Amount ◽  
Building Blocks ◽  
Β Blocker ◽  
Β Blockers ◽  
Optical Rotations ◽  
Reported Data ◽  
By Products

Sustainable methods for producing enantiopure drugs have been developed. Chlorohydrins as building blocks for several β-blockers have been synthesized in high enantiomeric purity by chemo-enzymatic methods. The yield of the chlorohydrins increased by the use of catalytic amount of base. The reason for this was found to be the reduced formation of the dimeric by-products compared to the use of higher concentration of the base. An overall reduction of reagents and reaction time was also obtained compared to our previously reported data of similar compounds. The enantiomers of the chlorohydrin building blocks were obtained by kinetic resolution of the racemate in transesterification reactions catalyzed by Candida antarctica Lipase B (CALB). Optical rotations confirmed the absolute configuration of the enantiopure drugs. The β-blocker (S)-practolol ((S)-N-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide) was synthesized with 96% enantiomeric excess (ee) from the chlorohydrin (R)-N-(4-(3-chloro-2 hydroxypropoxy)phenyl)acetamide, which was produced in 97% ee and with 27% yield. Racemic building block 1-((1H-indol-4-yl)oxy)-3-chloropropan-2-ol for the β-blocker pindolol was produced in 53% yield and (R)-1-((1H-indol-4-yl)oxy)-3-chloropropan-2-ol was produced in 92% ee. The chlorohydrin 7-(3-chloro-2-hydroxypropoxy)-3,4-dihydroquinolin-2(1H)-one, a building block for a derivative of carteolol was produced in 77% yield. (R)-7-(3-Chloro-2-hydroxypropoxy)-3,4-dihydroquinolin-2(1H)-one was obtained in 96% ee. The S-enantiomer of this carteolol derivative was produced in 97% ee in 87% yield. Racemic building block 5-(3-chloro-2-hydroxypropoxy)-3,4-dihydroquinolin-2(1H)-one, building block for the drug carteolol, was also produced in 53% yield, with 96% ee of the R-chlorohydrin (R)-5-(3-chloro-2-hydroxypropoxy)-3,4-dihydroquinolin-2(1H)-one. (S)-Carteolol was produced in 96% ee with low yield, which easily can be improved.

scholarly journals Controlled Synthesis of Linear Polyamidoamino Acids

Polymers ◽  
2019 ◽  
Vol 11 (8) ◽  
pp. 1324 ◽  
Author(s):  
Federica Ferruti ◽  
Jenny Alongi ◽  
Amedea Manfredi ◽  
Elisabetta Ranucci ◽  
Paolo Ferruti
Keyword(s):  
Amino Acids ◽  
Building Blocks ◽  
Synthetic Polymers ◽  
Polymerization Process ◽  
Random Copolymers ◽  
Controlled Synthesis ◽  
Molecular Weights ◽  
Synthetic Procedure ◽  
Low Solubility ◽  
By Products

Polyamidoamino acids (PAACs) are synthetic polymers prepared by the polyaddition of bisacrylamides with natural α-amino acids, which in the process maintain both their chirality and their amphoteric nature. This polymerization process is slow, but has the merits of taking place in water and of neither involving protection/de-protection steps nor releasing by-products. However, it leads to polydisperse polymers and, using α-amino acids mixtures, random copolymers. This paper presents a step-by-step polyaddition process leading to homo- and copolymeric PAACs with controlled sequences and controlled molecular weights. It exploits the much different rates of the two Michael addition steps of NH2 of α-amino acids with acrylamides, and the low solubility in organic solvents of the α-amino acid addition products. As a proof of principle, the controlled synthesis of the PAAC from l-arginine and N,N′-methylenebisacrylamide was performed up to a monodisperse product with 11 monomeric units and molecular weight 1840. This synthetic procedure was also tested with l-alanine. All intermediates were isolated and characterized. Noticeably, all of them were α,ω-difunctionalized with either acrylamides or sec-amines and were, in fact, building blocks with potential for preparing complex macromolecular architectures. In a first instance, copolymers with controlled sequences of amidoamine- and amidoamino acid units were prepared.

Isolation, Derivatization and Bioactive Properties of Natural Lignin Based Hydroxycinnamic Acids: A Review

2020 ◽  
Vol 17 ◽  
Author(s):  
Ramandeep Kaur ◽  
Mansi Goyal
Keyword(s):  
Phenolic Acids ◽  
Building Blocks ◽  
Syringic Acid ◽  
Hydroxycinnamic Acids ◽  
Bioactive Properties ◽  
Research Findings ◽  
Phenolic Polymer ◽  
Forestry Residues ◽  
By Products

Abstract:: Lignin, one of the major components of lignocellulosic materials, is the largest natural source of aromatic building blocks on the planet having high service potential for producing valuable chemicals and fuels. It is surrounded by an extensive network of hemicellulose and cellulose in lignocelluloses such as agricultural residues, processing by-products, forestry residues, etc. Therefore, its extraction needs proper procedures, which have been researched worldwide in the past few decades. Lignin is a complex phenolic polymer with hydroxycinnamyl alcohols i.e. p-coumaryl alcohol, coniferyl alcohol and sinapyl alcohol as its monomers. Also, lignin based phenolic acids i.e. substituted hydroxycinnamic acids such as pcoumaric acid, ferulic acid, caffeic acid, syringic acid, are core structural moieties in various drug categories such as antimicrobial, anti‐inflammatory, analgesic, anti-tyrosinase, antihistamine, antirheumatic and anti-thrombosis agents. Therefore, differently substituted hydroxycinnamic acids isolated from lignin have been explored recently with a view of dual advantage of valorization of unavoidable wastes; and exploiting drugs, which would probably have no harmful side effects because of their natural origin. In this review, recent research findings on the extraction of lignin followed by classification of natural phenolic acids, isolation of substituted hydroxycinnamic acids from lignin and their derivatization for various bioactive properties are discussed.

scholarly journals Organic Wastes as Feedstocks for Non-Conventional Yeast-Based Bioprocesses

2019 ◽  
Vol 7 (8) ◽  
pp. 229 ◽  
Author(s):  
Diem T. Hoang Do ◽  
Chrispian W. Theron ◽  
Patrick Fickers
Keyword(s):  
Carbon Sources ◽  
Value Added ◽  
Building Blocks ◽  
Organic Wastes ◽  
Cell Factory ◽  
Microbial Cell Factories ◽  
Cell Factories ◽  
Alternative Feedstocks ◽  
Global Population ◽  
By Products

Non-conventional yeasts are efficient cell factories for the synthesis of value-added compounds such as recombinant proteins, intracellular metabolites, and/or metabolic by-products. Most bioprocess, however, are still designed to use pure, ideal sugars, especially glucose. In the quest for the development of more sustainable processes amid concerns over the future availability of resources for the ever-growing global population, the utilization of organic wastes or industrial by-products as feedstocks to support cell growth is a crucial approach. Indeed, vast amounts of industrial and commercial waste simultaneously represent an environmental burden and an important reservoir for recyclable or reusable material. These alternative feedstocks can provide microbial cell factories with the required metabolic building blocks and energy to synthesize value-added compounds, further representing a potential means of reduction of process costs as well. This review highlights recent strategies in this regard, encompassing knowledge on catabolic pathways and metabolic engineering solutions developed to endow cells with the required metabolic capabilities, and the connection of these to the synthesis of value-added compounds. This review focuses primarily, but not exclusively, on Yarrowia lipolytica as a yeast cell factory, owing to its broad range of naturally metabolizable carbon sources, together with its popularity as a non-conventional yeast.

scholarly journals Metabolic Engineering of Bacillus subtilis for 2.3-BDO production by introducing an exogenous NADPH/NADP+ regeneration system

2019 ◽  
Author(s):  
Huiling Liu ◽  
Shuangying Liu ◽  
Fengyu Xie ◽  
Xian Zhang ◽  
Meijuan Xu ◽  
...  
Keyword(s):  
Bacillus Subtilis ◽  
Metabolic Engineering ◽  
Carbon Flux ◽  
Glucose Dehydrogenase ◽  
Transcriptional Regulator ◽  
Pentose Phosphate ◽  
Regeneration System ◽  
Nadph Regeneration ◽  
By Products ◽  
Regeneration Systems

Abstract Background: Generally, glucose is transformed into pyruvate from glycolysis before the target products acetoin and 2,3-butanediol (2,3-BDO) are formed. Pentose Phosphate Pathway (PPP) is an inefficient synthetic pathway for pyruvate production from glucose in Bacillus subtilis. Previously, it was found that engineered PPP in B. subtilis unbalanced NADH and NADPH regeneration systems and affected acetoin and 2,3 -BDO production.Results: In this study, metabolic engineering strategies were proposed to redistribute carbon flux to 2,3-BDO via reconstructing intracellular cofactors regeneration systems. Firstly, extra copies of glucose dehydrogenase (GDH)and an exogenous NADPH-dependent 2,3-BDO dehydrogenase (TDH) were introduced into the GRAS strain B. subtilis 168 to introduce an exogenous NADPH/NADP + regeneration system and broaden 2,3-BDO production pathway. It was found that overexpressing the NADPH/NADP + regeneration system effectively improved 2,3-BDO production and inhibited NADH-dependent by-products accumulation. Subsequently, the disruption of lactate dehydrogenase (encoded by ldh ) by insertion of the transcriptional regulator ALsR, essential for the expression of alsSD (encoding two key enzymes for the conversion of pyruvate to acetoin) in B. subtilis, resulted in the recombinant strain in which alsSD was overexpressed and the pathway to lactate was blocked simultaneously. On fermentation by the result engineered strain, the highest 2,3-BDO concentration increased by18.43%, while the titers of main byproducts acetoin and lactate decreased by 22.03% and 64%, respectively.Conclusion: In this study, it shows that engineering PPP and reconstructing intracellular cofactors regeneration system could be an alternative strategy in the metabolic engineering of 2,3-BDO production in B. subtilis .

scholarly journals Transamination-Like Reaction Catalyzed by Leucine Dehydrogenase for Efficient Co-Synthesis of α-Amino Acids and α-Keto Acids

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7287
Author(s):  
Xiaoqing Mu ◽  
Xian Feng ◽  
Tao Wu ◽  
Feng Zhou ◽  
Yao Nie ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Building Blocks ◽  
Regeneration System ◽  
Kinetics Parameters ◽  
Leucine Dehydrogenase ◽  
Keto Acids ◽  
Pharmaceutical Industries ◽  
Total Turnover ◽  
Acid Substrate

α-Amino acids and α-keto acids are versatile building blocks for the synthesis of several commercially valuable products in the food, agricultural, and pharmaceutical industries. In this study, a novel transamination-like reaction catalyzed by leucine dehydrogenase was successfully constructed for the efficient enzymatic co-synthesis of α-amino acids and α-keto acids. In this reaction mode, the α-keto acid substrate was reduced and the α-amino acid substrate was oxidized simultaneously by the enzyme, without the need for an additional coenzyme regeneration system. The thermodynamically unfavorable oxidation reaction was driven by the reduction reaction. The efficiency of the biocatalytic reaction was evaluated using 12 different substrate combinations, and a significant variation was observed in substrate conversion, which was subsequently explained by the differences in enzyme kinetics parameters. The reaction with the selected model substrates 2-oxobutanoic acid and L-leucine reached 90.3% conversion with a high total turnover number of 9.0 × 106 under the optimal reaction conditions. Furthermore, complete conversion was achieved by adjusting the ratio of addition of the two substrates. The constructed reaction mode can be applied to other amino acid dehydrogenases in future studies to synthesize a wider range of valuable products.

scholarly journals Channeling C1 Metabolism toward S-Adenosylmethionine-Dependent Conversion of Estrogens to Androgens in Estrogen-Degrading Bacteria

mBio ◽  
2020 ◽  
Vol 11 (4) ◽  
Author(s):  
Christian Jacoby ◽  
Joris Krull ◽  
Jennifer Andexer ◽  
Nico Jehmlich ◽  
Martin von Bergen ◽  
...  
Keyword(s):  
Large Scale ◽  
Regeneration System ◽  
Content Type ◽  
Methyl Donors ◽  
Denitrifying Bacterium ◽  
Methyl Donor ◽  
Methyl Transfer ◽  
Degrading Bacteria ◽  
Endocrine Disrupting ◽  
17Β Estradiol

ABSTRACT Bacterial degradation of endocrine disrupting and carcinogenic estrogens is essential for their elimination from the environment. Recent studies of the denitrifying, estrogen-degrading Denitratisoma strain DHT3 revealed the conversion of estrogens to androgens by a putative cobalamin-dependent methyltransferase encoded by the emtABCD genes. The methyl donor and its continuous regeneration to initiate estradiol catabolism have remained unknown. Here, large-scale cultivation of the denitrifying bacterium Denitratisoma oestradiolicum with estrogen provided the biomass required for quantitative biochemical analyses. Soluble fractions of extracts from estradiol-grown cells catalyzed the S-adenosyl-l-methionine (SAM)- and Ti(III)-citrate-dependent conversion of 17β-estradiol/estrone to the respective androgens at 0.15 nmol min−1 mg−1. Kinetic studies of 17β-estradiol methylation and reverse 1-dehydrotestosterone demethylation reactions indicated that the exergonic methyl transfer from SAM to the putative cobalamin drives the endergonic methyl transfer from the methylcobalamin intermediate to the phenolic ring A. Based on a high-quality circular genome from D. oestradiolicum, proteogenomic analyses identified a 17β-estradiol-induced gene cluster comprising emtABCD genes together with genes involved in SAM regeneration via l-serine and l-methionine. Consistent with this finding, l-methionine/ATP or l-serine/ATP/tetrahydrofolate/l-homocysteine substituted for SAM as methyl donors, further confirmed by the incorporation of the 13C-methyl-group from 13C-l-methonine into methyl(III)cobalamine and the estrone methylation product androsta-1,4-diene-3-one. This work demonstrates that during bacterial estrogen catabolism, the C1 pool is channeled toward the initiating methyl transfer to ring A. The effective cellular SAM regeneration system may serve as a model for whole-cell SAM-dependent methylation reactions of biotechnological interest. IMPORTANCE Estrogens comprise a group of related hormones occurring in predominantly female vertebrates, with endocrine disrupting and carcinogenic potential. Microbial biodegradation of estrogens is essential for their elimination from surface waters and wastewater. Aerobic bacteria employ oxygenases for the initial cleavage of the aromatic ring A. In contrast, anaerobic degradation of estrogens is initiated by methyl transfer-dependent conversion into androgens involving a putative cobalamin-dependent methyltransferase system. The methyl donor for this unprecedented reaction and its stoichiometric regeneration have remained unknown. With the biomass obtained from large-scale fermentation of an estrogen-degrading denitrifying bacterium, we identified S-adenosyl-methionine (SAM) as the methyl donor for the cobalamin-mediated methyl transfer to estrogens. To continuously supply C1 units to initiate estrogen degradation, genes for SAM regeneration from estradiol-derived catabolites are highly upregulated. Data presented here shed light into biochemical processes involved in the globally important microbial degradation of estrogens.

scholarly journals Lignin as an Active Biomaterial: A Review

2021 ◽  
Vol 9 (1) ◽  
pp. 1
Author(s):  
Nissa Nurfajrin Solihat ◽  
Fahriya Puspita Sari ◽  
Faizatul Falah ◽  
Maya Ismayati ◽  
Muhammad Adly Rahandi Lubis ◽  
...  
Keyword(s):  
Cell Wall ◽  
Antimicrobial Agent ◽  
Building Blocks ◽  
Active Packaging ◽  
Pulp And Paper ◽  
Wide Range ◽  
Potential Applications ◽  
Modified Lignin ◽  
Pulp And Paper Industries ◽  
By Products

Lignin is the second most naturally abundant biopolymer in the cell wall of lignocellulosic compound (15-35%) after cellulose.Lignin can be generated in massive amounts as by-products in biorefineries and pulp and paper industries through differing processes. Most lignin is utilized as generating energy and has always been treated as waste. Due to the high amount of phenolic compounds in lignin, it is considered as a potential material for various polymers, building blocks, and biomaterials production. Even though lignin can be utilized in the form of isolated lignin directly, the modification of lignin can increase the wide range of lignin applications. Lignin-based copolymers and modified lignin show better miscibility with another polymeric matrix, outstanding to the enhanced performance of such lignin-based polymer composites.This article summarizes the properly updated information of lignin’s potential applications, such as bio-surfactant, active packaging, antimicrobial agent, and supercapacitor.Keywords: active packaging, antimicrobial agent, bio-surfactant, lignin, supercapacitor

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