Biocatalytic Imine Reduction and Reductive Amination of Ketones

2015 ◽  
Vol 357 (8) ◽  
pp. 1655-1685 ◽  
Author(s):  
Joerg H. Schrittwieser ◽  
Stefan Velikogne ◽  
Wolfgang Kroutil
Keyword(s):  
Reductive Amination ◽  
Imine Reduction

ChemInform Abstract: Biocatalytic Imine Reduction and Reductive Amination of Ketones

ChemInform ◽  
2015 ◽  
Vol 46 (30) ◽  
pp. no-no
Author(s):  
Joerg H. Schrittwieser ◽  
Stefan Velikogne ◽  
Wolfgang Kroutil
Keyword(s):  
Reductive Amination ◽  
Imine Reduction

scholarly journals Cover Picture: Biocatalytic Imine Reduction and Reductive Amination of Ketones (Adv. Synth. Catal. 8/2015)

2015 ◽  
Vol 357 (8) ◽  
pp. 1553-1553 ◽  
Author(s):  
Joerg H. Schrittwieser ◽  
Stefan Velikogne ◽  
Wolfgang Kroutil
Keyword(s):  
Reductive Amination ◽  
Imine Reduction

Imine Reduction and Reductive Amination

2007 ◽  
pp. 161-181
Author(s):  
Magnus Rueping ◽  
Erli Sugiono ◽  
Cengiz Azap ◽  
Thomas Theissmann ◽  
Andrey P. Antonchick ◽  
...  
Keyword(s):  
Reductive Amination ◽  
Imine Reduction

scholarly journals Characterization of imine reductases in reductive amination for the exploration of structure-activity relationships

2020 ◽  
Vol 6 (21) ◽  
pp. eaay9320 ◽  
Author(s):  
Sarah L. Montgomery ◽  
Ahir Pushpanath ◽  
Rachel S. Heath ◽  
James R. Marshall ◽  
Ulrike Klemstein ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Reductive Amination ◽  
Chiral Amines ◽  
Sequence Motif ◽  
Sequence Structure ◽  
Reaction Conditions ◽  
Rational Engineering ◽  
Structure Activity ◽  
Imine Reduction

Imine reductases (IREDs) have shown great potential as catalysts for the asymmetric synthesis of industrially relevant chiral amines, but a limited understanding of sequence activity relationships makes rational engineering challenging. Here, we describe the characterization of 80 putative and 15 previously described IREDs across 10 different transformations and confirm that reductive amination catalysis is not limited to any particular subgroup or sequence motif. Furthermore, we have identified another dehydrogenase subgroup with chemoselectivity for imine reduction. Enantioselectivities were determined for the reduction of the model substrate 2-phenylpiperideine, and the effect of changing the reaction conditions was also studied for the reductive aminations of 1-indanone, acetophenone, and 4-methoxyphenylacetone. We have performed sequence-structure analysis to help explain clusters in activity across a phylogenetic tree and to inform rational engineering, which, in one case, has conferred a change in chemoselectivity that had not been previously observed.

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>

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