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Methods in Molecular Biology (Clifton,... 2010Surface plasmon resonance (SPR) is one of the leading tools in biomedical research. The challenge in its use is the controlled positioning of one of the components of an...
Surface plasmon resonance (SPR) is one of the leading tools in biomedical research. The challenge in its use is the controlled positioning of one of the components of an interaction on a carefully designed surface. Many attempts in interaction analysis fail due to the non-functional or unsuccessful immobilization of a reactant onto the complex matrix of that surface. The most common technique for linking ligands covalently to a hydrophilic solid surface is amine coupling via reactive esters. In this chapter detailed methods and problem discussions will be given to assist in fast decision analysis to optimize immobilization and regeneration. Topics in focus are different coupling techniques for small and large molecules, streptavidin-biotin sandwich immobilization, and optimizing regeneration conditions.
Topics: Aldehydes; Amination; Amines; Biotin; Carbodiimides; Immobilized Proteins; Oxidation-Reduction; Streptavidin; Succinimides; Surface Plasmon Resonance; Surface Properties
PubMed: 20217613
DOI: 10.1007/978-1-60761-670-2_3 -
Chemical Communications (Cambridge,... Dec 2022Direct amination of C-H or CC bonds using unprotected amino groups is very challenging, especially with earth abundant metal ions. Here we show that a bioinspired...
Direct amination of C-H or CC bonds using unprotected amino groups is very challenging, especially with earth abundant metal ions. Here we show that a bioinspired iron(II) complex catalyses the double amination of its dangling benzyl branch in the presence of hydroxylamine derivatives as the unprotected amine donor and that the replacement of the benzyl branch by a methyl group also allows the aziridination of styrene.
Topics: Amines; Iron; Metals; Amination; Ferrous Compounds
PubMed: 36468296
DOI: 10.1039/d2cc04992a -
Applied Microbiology and Biotechnology Jan 2019In this mini-review, an overview about various developed strategies for accessing industrially relevant primary n-alkyl amines via reductive amination by means of amine... (Review)
Review
In this mini-review, an overview about various developed strategies for accessing industrially relevant primary n-alkyl amines via reductive amination by means of amine dehydrogenases as well as transaminases is given. Such transformations were combined with in situ cofactor recycling methodologies avoiding the need for addition of external stoichiometric amounts of organic co-substrates. These methods comprise the application of natural photosynthesis with algae when using carbonyl compounds as substrates as well as the utilization of alcohols as substrates in combination with self-sufficient biocatalytic systems. As such a feature is of utmost importance for large-scale biotransformations in the field of bulk chemicals, which represent high-volume but low-price chemicals, the achievements open up a perspective for biocatalysis also in the area of commodity chemicals. Besides approaches to n-alkyl amines and cyclohexylamine, recently also biocatalytic cascades towards n-alkyl amines bearing functionalities in the ω-position such as a carboxylic acid ester or amino group were reported. It is noteworthy that for ω-aminolauric acid, such a process has already been demonstrated on pilot plant scale.
Topics: Alcohols; Amination; Amines; Biocatalysis; Biotechnology; Chlamydomonas reinhardtii; Coenzymes; Diamines; Oxidoreductases; Polymers; Transaminases
PubMed: 30367182
DOI: 10.1007/s00253-018-9452-0 -
ChemSusChem Apr 2022One-pot synthesis of sustainable primary amines by catalytic reductive amination of bio-based carbonyl compounds with NH and H is emerging as a promising and robust... (Review)
Review
One-pot synthesis of sustainable primary amines by catalytic reductive amination of bio-based carbonyl compounds with NH and H is emerging as a promising and robust approach. The primary amines, especially furfuryl amine (FUA) derived from furfural (FUR), with a wide range of applications from pharmaceuticals to agrochemicals, have attracted much attention due to their versatility. This Review is majorly comprised of two segments on the reductive amination of FUR to FUA, one with precious (Ru, Pd, Rh) and the other with non-precious (Co, Ni) metals on different supports and in various solvent systems in the presence of NH and H . The active metal sites generated on multiple supports are accentuated with experimental evidence based on CO-diffuse reflectance infrared Fourier-transform spectroscopy, H temperature-programmed reduction, X-ray photoelectron spectroscopy, and calorimetry. Moreover, this Review comprehensively describes the role of acidic and basic support for the metal on the yield of FUA. Overall, this Review provides an insight into how to design and develop an efficiently robust catalyst for the selective reductive amination of a broad spectrum of carbonyl compounds to corresponding amines.
Topics: Amination; Amines; Catalysis; Furaldehyde; Metals
PubMed: 35171526
DOI: 10.1002/cssc.202200107 -
Chembiochem : a European Journal of... May 2022Native amine dehydrogenases (nat-AmDHs) have recently emerged as a potentially valuable new reservoir of enzymes for the sustainable and selective synthesis of chiral...
Native amine dehydrogenases (nat-AmDHs) have recently emerged as a potentially valuable new reservoir of enzymes for the sustainable and selective synthesis of chiral amines, catalyzing the NAD(P)H-dependent ammoniation of carbonyl compounds with high activity and selectivity. MATOUAmDH2, recently identified from the Marine Atlas of Tara Oceans Unigenes (MATOUv1) database of eukaryotic genes, displays exceptional catalytic performance against its best identified substrate, isobutyraldehyde, as well as having broader substrate scope than other nat-AmDHs. In the interests of providing a platform for the rational engineering of this and other nat-AmDHs, we have determined the structure of MATOUAmDH2 in complex with NADP and also with the cofactor and cyclohexylamine. Monomers within the structure are representative of more open and closed conformations of the enzyme and illustrate the profound changes undergone by nat-AmDHs during the catalytic cycle. An alanine screen of active site residues revealed that M215A and L180A are more active than the wild-type enzyme for the amination of cyclohexanone with ammonia and methylamine respectively; the latter suggests that AmDHs have the potential to be engineered for the improved production of secondary amines.
Topics: Amination; Amines; Biocatalysis; Mutation; NAD; NADP; Oxidoreductases; Substrate Specificity
PubMed: 35349204
DOI: 10.1002/cbic.202200136 -
Chemistry, An Asian Journal Apr 2016A practical synthesis of highly functionalized amines by the formal hydroamination reaction of alkenes with nitroarenes catalyzed by an air stable amine-bis(phenolate)...
A practical synthesis of highly functionalized amines by the formal hydroamination reaction of alkenes with nitroarenes catalyzed by an air stable amine-bis(phenolate) iron(III) complex is reported. The reaction uses an easily handled silane, low catalyst loadings, and mild reaction conditions. A wide range of substrates are transformed with synthetically useful yields (21 examples).
Topics: Alkenes; Amination; Amines; Catalysis; Ferric Compounds; Molecular Structure; Phenols
PubMed: 26864731
DOI: 10.1002/asia.201501098 -
Chembiochem : a European Journal of... Jun 2017Amine transaminase (ATA) catalyzing stereoselective amination of prochiral ketones is an attractive alternative to transition metal catalysis. As wild-type ATAs do not...
Amine transaminase (ATA) catalyzing stereoselective amination of prochiral ketones is an attractive alternative to transition metal catalysis. As wild-type ATAs do not accept sterically hindered ketones, efforts to widen the substrate scope to more challenging targets are of general interest. We recently designed ATAs to accept aromatic and thus planar bulky amines, with a sequence-based motif that supports the identification of novel enzymes. However, these variants were not active against 2,2-dimethyl-1-phenyl-propan-1-one, which carries a bulky tert-butyl substituent adjacent to the carbonyl function. Here, we report a solution for this type of substrate. The evolved ATAs perform asymmetric synthesis of the respective R amine with high conversions by using either alanine or isopropylamine as amine donor.
Topics: Amination; Amines; Amino Acid Substitution; Biocatalysis; Computer Simulation; Directed Molecular Evolution; Protein Engineering; Substrate Specificity; Transaminases
PubMed: 28334484
DOI: 10.1002/cbic.201700033 -
Organic Letters Aug 2022The sturdy chelation of 1,2-diamines and transition-metals would retard or even interrupt the routine catalytic cycles. In the amidation and asymmetric reductive...
The sturdy chelation of 1,2-diamines and transition-metals would retard or even interrupt the routine catalytic cycles. In the amidation and asymmetric reductive amination (ARA) cascade reactions of diamines and ketoesters, we deployed sets of additives to ensure a smooth transformation catalyzed by the complexes of rhodium and versatile and highly modular phosphoramidite-phosphine ligands. The tunability of the ligands was fully exploited to accommodate various diamines and α-ketoesters for the efficient synthesis of chiral 3,4-dihydroquinoxalinones.
Topics: Amination; Amines; Catalysis; Diamines; Ligands; Rhodium
PubMed: 35916628
DOI: 10.1021/acs.orglett.2c01728 -
Organic Letters Jun 2017The incorporation of fluorine into organic scaffolds often improves the bioactivity of pharmaceutically relevant compounds. C-F/C-N/C-O stereotriad motifs are prevalent...
The incorporation of fluorine into organic scaffolds often improves the bioactivity of pharmaceutically relevant compounds. C-F/C-N/C-O stereotriad motifs are prevalent in antivirals, neuraminidase inhibitors, and modulators of androgen receptors, but are challenging to install. An oxidative allene amination strategy using Selectfluor rapidly delivers triply functionalized triads of the form C-F/C-N/C-O, exhibiting good scope and diastereoselectivity for all syn products. The resulting stereotriads are readily transformed into fluorinated pyrrolidines and protected α-, β-, and γ-amino acids.
Topics: Alkadienes; Amination; Amines; Catalysis; Molecular Structure; Stereoisomerism
PubMed: 28573862
DOI: 10.1021/acs.orglett.7b01342 -
Journal of Environmental Management Mar 2016A low-cost solid amine adsorbent for CO2 capture was prepared by using sugarcane bagasse (SB), a dominant agro-industrial residue in the sugar and alcohol industry as...
A low-cost solid amine adsorbent for CO2 capture was prepared by using sugarcane bagasse (SB), a dominant agro-industrial residue in the sugar and alcohol industry as raw materials. In this preparation process, acrylamide was grafted on SB, and the grafted fiber was then aminated with different type of amine reagents to introduce primary and secondary amine groups onto the surface of SB fibers. The graft and amination conditions were optimized. The prepared solid amine adsorbent showed remarkable CO2 adsorption capacity and the adsorption capacity of the solid amine adsorbent could reach 5.01 mmol CO2/g at room temperature. The comparison of adsorption capacities of amine fibers aminated with various amination agents demonstrated that fibers aminated with triethylenetetramine would obtain higher adsorption capacities and higher amine efficiency. These adsorbents also showed good regeneration performance, the regenerated adsorbent could maintain almost the same adsorption capacity for CO2 after 10 recycles.
Topics: Acrylamide; Adsorption; Amination; Amines; Carbon Dioxide; Cellulose; Environmental Restoration and Remediation; Saccharum
PubMed: 26706226
DOI: 10.1016/j.jenvman.2015.09.033