Enzymatic Synthesis of Aliphatic Primary ω-Amino Alcohols from ω-Amino Fatty Acids by Carboxylic Acid Reductase

2020 ◽  
Vol 150 (11) ◽  
pp. 3079-3085 ◽  
Author(s):  
Sharad Sarak ◽  
Hyunwoo Jeon ◽  
Mahesh D. Patil ◽  
Taresh P. Khobragade ◽  
Amol D. Pagar ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Carboxylic Acid ◽  
Enzymatic Synthesis ◽  
Amino Alcohols

scholarly journals One-Step Biocatalytic Synthesis of Sustainable Surfactants Using Selective Amide Bond Formation

2021 ◽  
Author(s):  
Max Lubberink ◽  
Christian Schnepel ◽  
Christopher Baldwin ◽  
Nicholas Turner ◽  
Sabine Flitsch
Keyword(s):  
Fatty Acids ◽  
Carboxylic Acid ◽  
Enzymatic Synthesis ◽  
Bond Formation ◽  
Amide Bond ◽  
Esterification Reaction ◽  
Amide Bond Formation ◽  
Selective Strategy ◽  
One Step ◽  
Acyl Phosphate

N-alkanoyl-N-methylglucamides (MEGAs) are non-toxic surfactants widely used in pharmaceutical and biochemical applications and hence more sustainable syntheses towards these compounds are highly desired. Here we present an aqueous, enzymatic synthesis route towards MEGAs and analogues using carboxylic acid reductase (CAR), which has been engineered to catalyse amide bond formation (CAR-A). Compared to lipase catalysed reactions, this biocatalyst is capable of selective amide bond formation between amino-polyols and fatty acids without the competing esterification reaction being observed. The wide substrate scope of CAR-A catalysed amidation was exemplified by the synthesis of 16 amides including several commercially relevant targets. The ATP co-factor could be recycled from cheap polyphosphate using a kinase. This work establishes acyl-phosphate mediated chemistry as a selective strategy for biocatalytic amide bond formation in the presence of competing alcohol functionalities.

scholarly journals Enzymatic Synthesis of Cyclopropane Fatty Acids Catalyzed by Bacterial Extracts

1963 ◽  
Vol 238 (4) ◽  
pp. 1242-1248
Author(s):  
H. Zalkin ◽  
John H. Law ◽  
Howard Goldfine
Keyword(s):  
Fatty Acids ◽  
Enzymatic Synthesis ◽  
Cyclopropane Fatty Acids

Enantioselective Enzymatic Synthesis of ( R )‐Phenyl Alkyl Esters and Their Analogue Amides using Fatty Acids as Green Acyl Donors.

2021 ◽  
Vol 6 (48) ◽  
pp. 13941-13946
Author(s):  
Nour ElHouda Benamara ◽  
Mounia Merabet‐Khelassi ◽  
Samia Guezane Lakoud ◽  
Louisa Aribi‐Zouioueche ◽  
Olivier Riant
Keyword(s):  
Fatty Acids ◽  
Enzymatic Synthesis ◽  
Alkyl Esters ◽  
Acyl Donors

THE APPLICATION OF THE ARNDT–EISTERT REACTION TO THE SYNTHESIS OF FATTY ACIDS OF HIGH MOLECULAR WEIGHT

1950 ◽  
Vol 28b (9) ◽  
pp. 556-560 ◽  
Author(s):  
F. A. Vandenheuvel ◽  
P. Yates
Keyword(s):  
Fatty Acids ◽  
Molecular Weight ◽  
Carboxylic Acid ◽  
Stearic Acid ◽  
High Molecular Weight ◽  
Efficient Method ◽  
Convenient Method ◽  
Ultraviolet Absorption ◽  
Aliphatic Carboxylic Acid ◽  
Eicosanoic Acid

The Arndt–Eistert reaction offers a convenient method for the synthesis of the higher members of the aliphatic carboxylic acid series. Nonadecanoic acid, eicosanoic acid, and heneicosanoic acid have been prepared successively from stearic acid in good yields. An efficient method of purification of the synthetic products is described. The ultraviolet absorption maxima for some diazoketones derived from the higher members of the aliphatic carboxylic acid series are recorded.

scholarly journals Effects of adrenaline on ketogenesis from long- and medium-chain fatty acids in starved rats

1982 ◽  
Vol 204 (3) ◽  
pp. 749-756 ◽  
Author(s):  
M C Sugden ◽  
D I Watts ◽  
C E Marshall
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Blood Glucose ◽  
Carboxylic Acid ◽  
Chain Length ◽  
Clinical Significance ◽  
Ketone Body ◽  
Medium Chain ◽  
Medium Chain Fatty Acids ◽  
Increase Blood Glucose

1. Injection of adrenaline into 24 h-starved rats caused a 69% decrease in blood [ketone-body] (3-hydroxybutyrate plus acetoacetate), accompanied by a decreased [3-hydroxybutyrate]/[acetoacetate] ratio. Blood [glucose] and [lactate] increased, but [alanine] was unchanged. 2. Adrenaline also decreased [ketone-body] after intragastric feeding of both long- and medium-chain triacylglycerol. The latter decrease was observed after suppression of lipolysis with 5-methylpyrazole-3-carboxylic acid, indicating that the antiketogenic action of adrenaline was not dependent on the chain length of the precursor fatty acid. 3. The actions of adrenaline to decrease blood [ketone-body] and to increase blood [glucose] were not observed after administration of 3-mercaptopicolinate, an inhibitor of gluconeogenesis. This suggests that these effects of the hormone are related. 4. The possible clinical significance of the results is discussed with reference to the restricted ketosis often observed after surgical or orthopaedic injury.

A biocatalytic cascade for the conversion of fatty acids to fatty amines

2019 ◽  
Vol 21 (18) ◽  
pp. 4932-4935 ◽  
Author(s):  
Joan Citoler ◽  
Sasha R. Derrington ◽  
James L. Galman ◽  
Han Bevinakatti ◽  
Nicholas J. Turner
Keyword(s):  
Fatty Acids ◽  
Carboxylic Acid ◽  
One Pot ◽  
Fatty Amines

A mild, biocatalytic alternative to the conventional amination of fatty acids through a one-pot tandem cascade performed by a carboxylic acid reductase (CAR) and a transaminase (ω-TA).

Sign in / Sign up

Export Citation Format

Share Document