Asymmetric Reductive Amination/Ring-Closing Cascade: Direct Synthesis of Enantioenriched Biaryl-Bridged NH Lactams

2020 ◽  
Vol 22 (16) ◽  
pp. 6479-6483 ◽  
Author(s):  
Yao Zhang ◽  
Yun-Qi Liu ◽  
Le’an Hu ◽  
Xumu Zhang ◽  
Qin Yin
Keyword(s):  
Reductive Amination ◽  
Direct Synthesis

Enantioselective Direct Synthesis of Free Cyclic Amines via Intramolecular Reductive Amination

2017 ◽  
Vol 19 (16) ◽  
pp. 4215-4218 ◽  
Author(s):  
Ying Zhang ◽  
Qiaozhi Yan ◽  
Guofu Zi ◽  
Guohua Hou
Keyword(s):  
Reductive Amination ◽  
Direct Synthesis ◽  
Cyclic Amines

Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters

2020 ◽  
Vol 22 (7) ◽  
pp. 2707-2713 ◽  
Author(s):  
Yongjie Shi ◽  
Xuefeng Tan ◽  
Shuang Gao ◽  
Yao Zhang ◽  
Jingxin Wang ◽  
...  
Keyword(s):  
Reductive Amination ◽  
Direct Synthesis ◽  
Keto Acids

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
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