solid-supported reductive amination

10.1039/sp86 ◽  
2001 ◽  
Author(s):  
Daniel Hamza
Keyword(s):  
Reductive Amination

Selective Functionalization at N2-Position of Guanine in Oligonucleotides via Reductive Amination

2020 ◽  
Author(s):  
Bapurao Bhoge ◽  
Ishu Saraogi
Keyword(s):  
Organic Chemistry ◽  
Chemical Biology ◽  
Reductive Amination ◽  
The Other ◽  
Dna Oligomers ◽  
Site Specific ◽  
Wide Applicability ◽  
Dna Oligonucleotides ◽  
Selective Functionalization

Chemo- and site-specific modifications in oligonucleotides have wide applicability as mechanistic probes in chemical biology. Here we have employed a classical reaction in organic chemistry, reductive amination, to selectively functionalize the N<sup>2</sup>-amine of guanine/2’-deoxyguanine monophosphate. This method specifically modifies guanine in several tested DNA oligonucleotides, while leaving the other bases unaffected. Using this approach, we have successfully incorporated desired handles chemoselectively into DNA oligomers.

Bringing Biocatalysis into the Deuteration Toolbox

2019 ◽  
Author(s):  
Jack Rowbotham ◽  
Oliver Lenz ◽  
Holly Reeve ◽  
Kylie Vincent
Keyword(s):  
Late Stage ◽  
Hydrogen Isotope ◽  
Reductive Amination ◽  
Mechanistic Studies ◽  
Ambient Conditions ◽  
Synthetic Pathway ◽  
Drug Candidates ◽  
Isotopic Selectivity ◽  
Reducing Equivalents

<p></p><p>Chemicals labelled with the heavy hydrogen isotope deuterium (<sup>2</sup>H) have long been used in chemical and biochemical mechanistic studies, spectroscopy, and as analytical tracers. More recently, demonstration of selectively deuterated drug candidates that exhibit advantageous pharmacological traits has spurred innovations in metal-catalysed <sup>2</sup>H insertion at targeted sites, but asymmetric deuteration remains a key challenge. Here we demonstrate an easy-to-implement biocatalytic deuteration strategy, achieving high chemo-, enantio- and isotopic selectivity, requiring only <sup>2</sup>H<sub>2</sub>O (D<sub>2</sub>O) and unlabelled dihydrogen under ambient conditions. The vast library of enzymes established for NADH-dependent C=O, C=C, and C=N bond reductions have yet to appear in the toolbox of commonly employed <sup>2</sup>H-labelling techniques due to requirements for suitable deuterated reducing equivalents. By facilitating transfer of deuterium atoms from <sup>2</sup>H<sub>2</sub>O solvent to NAD<sup>+</sup>, with H<sub>2</sub> gas as a clean reductant, we open up biocatalysis for asymmetric reductive deuteration as part of a synthetic pathway or in late stage functionalisation. We demonstrate enantioselective deuteration via ketone and alkene reductions and reductive amination, as well as exquisite chemo-control for deuteration of compounds with multiple unsaturated sites.</p><p></p>

Recent Advances in Reductive Amination Catalysis and Its Applications

2015 ◽  
Vol 19 (11) ◽  
pp. 1021-1049 ◽  
Author(s):  
Heshmatollah Alinezhad ◽  
Hossein Yavari ◽  
Fatemeh Salehian
Keyword(s):  
Reductive Amination ◽  
Recent Advances

Titanium(IV) Isopropoxide Mediated Solution Phase Reductive Amination on an Automated Platform: Application in the Generation of Urea and Amide Libraries

2000 ◽  
Vol 3 (2) ◽  
pp. 117-124 ◽  
Author(s):  
Sukanta Bhattacharyya ◽  
Lisa Fan ◽  
Lanchi Vo ◽  
Jeff Labadie
Keyword(s):  
Reductive Amination ◽  
Solution Phase ◽  
Automated Platform

ChemInform Abstract: A General and Direct Reductive Amination of Aldehydes and Ketones with Electron-Deficient Anilines.

ChemInform ◽  
2016 ◽  
Vol 47 (38) ◽  
Author(s):  
Jakob Pletz ◽  
Bernhard Berg ◽  
Rolf Breinbauer
Keyword(s):  
Reductive Amination ◽  
Aldehydes And Ketones

scholarly journals Highly Osmotic Oxidized Sucrose-Crosslinked Polyethylenimine for Gene Delivery Systems

Pharmaceutics ◽  
2021 ◽  
Vol 13 (1) ◽  
pp. 87
Author(s):  
Jaehong Park ◽  
Kyusik Kim ◽  
Sohee Jeong ◽  
Migyeom Lee ◽  
Tae-il Kim
Keyword(s):  
Gene Delivery ◽  
Reductive Amination ◽  
Transfection Efficiency ◽  
Delivery Systems ◽  
Buffering Capacity ◽  
Serum Stability ◽  
High Osmolality ◽  
Cox 2 ◽  
Serum Free Conditions ◽  
Positively Charged

In this work, highly osmotic oxidized sucrose-crosslinked polyethylenimine (SP2K) polymers were developed for gene delivery systems, and the transfection mechanism is examined. First, periodate-oxidized sucrose and polyethylenimine 2K (PEI2K) were crosslinked with various feed ratios via reductive amination. The synthesis was confirmed by 1H NMR and FTIR. The synthesized SP2K polymers could form positively charged (~40 mV zeta-potential) and nano-sized (150–200 nm) spherical polyplexes with plasmid DNA (pDNA). They showed lower cytotoxicity than PEI25K but concentration-dependent cytotoxicity. Among them, SP2K7 and SP2K10 showed higher transfection efficiency than PEI25K in both serum and serum-free conditions, revealing the good serum stability. It was found that SP2K polymers possessed high osmolality and endosome buffering capacity. The transfection experiments with cellular uptake inhibitors suggest that the transfection of SP2K polymers would progress by multiple pathways, including caveolae-mediated endocytosis. It was also thought that caveolae-mediated endocytosis of SP2K polyplexes would be facilitated through cyclooxygenase-2 (COX-2) expression induced by high osmotic pressure of SP2K polymers. Confocal microscopy results also supported that SP2K polyplexes would be internalized into cells via multiple pathways and escape endosomes efficiently via high osmolality and endosome buffering capacity. These results demonstrate the potential of SP2K polymers for gene delivery systems.

scholarly journals C-N Bond Formation by Consecutive Continuous-Flow Reductions towards A Medicinally Relevant Piperazine Derivative

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 2040
Author(s):  
Zsolt Fülöp ◽  
Péter Bana ◽  
István Greiner ◽  
János Éles
Keyword(s):  
Antipsychotic Drug ◽  
Catalytic Hydrogenation ◽  
Continuous Flow ◽  
Reductive Amination ◽  
Reduction Method ◽  
Bond Formation ◽  
Aluminum Salt ◽  
Line Extraction ◽  
Piperazine Derivative ◽  
Step Procedure

A new, continuous-flow consecutive reduction method was developed for the C-N bond formation in the synthesis of the key intermediate of the antipsychotic drug cariprazine. The two-step procedure consists of a DIBAL-H mediated selective ester reduction conducted in a novel, miniature alternating diameter reactor, followed by reductive amination using catalytic hydrogenation on 5% Pt/C. The connection of the optimized modules was accomplished using an at-line extraction to prevent precipitation of the aluminum salt byproducts.

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