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

Copper-catalyzed coupling of anthranils and α-keto acids: direct synthesis of α-ketoamides

2019 ◽  
Vol 17 (24) ◽  
pp. 5902-5907 ◽  
Author(s):  
Ping-Gui Li ◽  
Hao Zhu ◽  
Min Fan ◽  
Cheng Yan ◽  
Kai Shi ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Bond Formation ◽  
Aldehyde Group ◽  
Keto Acids

Copper-catalyzed coupling of α-keto acids with anthranils is reported for the synthesis of α-ketoamides bearing an aldehyde group via N–O/C–O bond cleavages and C–N bond formation.

Structure-guided engineering ofmeso-diaminopimelate dehydrogenase for enantioselective reductive amination of sterically bulky 2-keto acids

2018 ◽  
Vol 8 (19) ◽  
pp. 4994-5002 ◽  
Author(s):  
Xinkuan Cheng ◽  
Xi Chen ◽  
Jinhui Feng ◽  
Qiaqing Wu ◽  
Dunming Zhu
Keyword(s):  
Reductive Amination ◽  
Substrate Binding ◽  
Binding Pocket ◽  
Substrate Binding Pocket ◽  
Keto Acids

Structure-guided reshaping the substrate-binding pocket of ameso-diaminopimelate dehydrogenase (StDAPDH) led to a mutant W121L/H227I, which catalyzed the enantioselective reductive amination of some sterically bulky 2-keto acids.

Electrochemical synthesis of amino acids by reductive amination of keto acids. I. Reduction at mercury electrodes

1978 ◽  
Vol 31 (1) ◽  
pp. 73 ◽  
Author(s):  
EA Jeffery ◽  
A Meisters
Keyword(s):  
Reductive Amination ◽  
Phenylacetic Acid ◽  
Reduction Potential ◽  
Aqueous Ammonia ◽  
Saturated Calomel Electrode ◽  
Mercury Electrode ◽  
Ammonia Concentration ◽  
Initial Current ◽  
Keto Acids ◽  
Mercury Electrodes

Racemic 2-amino-2-phenylacetic acid, monoammonium glutamate, 2-aminobutyric acid, α-alanine and ammonium 5-amino-5-phenylvalerate have been prepared by electrochemical reductive amination of the corresponding keto acids in aqueous ammonia/ammonium chloride solution at a mercury electrode. The yields ranged from 24% for ammonium 5-amino-5-phenylvalerate to 88% for 2-amino-2-phenylacetic acid. The current efficiency and yield of 2-amino-2-phenylacetic acid from reductive amination of 2-oxo-2-phenylacetic acid increased with increase in ammonia concentration. Also, decreasing the reduction potential from -1.10 to -1.30 V (with respect to a saturated calomel electrode) in 2 M ammonia raised the initial current density from c. 2 mA/cm2 to c. 7 mA/cm2 but halved the yield of 2-amino-2-phenylacetic acid.

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

Reductive Amination of Keto Acids

2012 ◽  
pp. 1165-1203 ◽  
Author(s):  
Werner Hummel ◽  
Harald Gröger
Keyword(s):  
Reductive Amination ◽  
Keto Acids

Lactate-Based Ionic Liquid Catalyzed Reductive Amination/Cyclization of Keto Acids under Mild Conditions: A Metal-Free Route To Synthesize Lactams

ACS Catalysis ◽  
2017 ◽  
Vol 7 (11) ◽  
pp. 7772-7776 ◽  
Author(s):  
Cailing Wu ◽  
Hongye Zhang ◽  
Bo Yu ◽  
Yu Chen ◽  
Zhengang Ke ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Reductive Amination ◽  
Metal Free ◽  
Mild Conditions ◽  
Keto Acids

THE METABOLISM OF ASCARIS LUMBRICOIDES OVARIES: II. AMINO ACID METABOLISM

1955 ◽  
Vol 33 (1) ◽  
pp. 307-316 ◽  
Author(s):  
John K. Pollak ◽  
Donald Fairbairn
Keyword(s):  
Amino Acid ◽  
Reductive Amination ◽  
Acid Oxidase ◽  
Active Protein ◽  
Amino Acid Oxidase ◽  
Keto Acids ◽  
Glutamic Dehydrogenase ◽  
A Minor ◽  
Pyruvic Acids ◽  
Minor Reaction

Homogenates of ascaris ovaries contained transamination, deamination, and reductive amination systems. Alanine–glutamic and aspartic–glutamic transaminases were active, whereas weaker transaminations occurred between glycine or serine and α-ketoglutaric or pyruvic acids. Sixteen other amino acids did not participate in transamination with these keto acids. A minor reaction, however, occurred between alanine or glutamic acid and α-ketovaleric acid. No amino acid oxidase activity was detected, and deamination appeared to be limited to a weakly positive glutamic dehydrogenase, which could be coupled to the alanine–glutamic and aspartic–glutamic transaminases to form a transdeaminase system. In the presence of pyruvate and ammonium chloride reductive amination occurred and alanine and aspartic acid were synthesized. This reaction was accelerated by bicarbonate, although oxalacetate could not be substituted successfully for pyruvate in the amination system. The results of the investigation are in accord with the probability that an active protein synthesis occurs in ascaris ovaries.

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