Urea Cycle, Properties and Applications of Urea

CENTRAL ASIAN JOURNAL OF THEORETICAL
AND APPLIED SCIENCES

Volume: 04 Issue: 05 | May 2023 ISSN: 2660-5317
https://cajotas.centralasianstudies.org
Urea Cycle, Properties and Applications of Urea

Renu Tyagi, Rekha Kalani, Chandresh Pareek
Associate Professor in Chemistry, JDB Govt. Girls College, Kota Rajasthan, India
Received 4th Mar 2023, Accepted 6th Apr 2023, Online 3rd May 2023
Abstract: Urea, also known as carbamide, is an organic compound with chemical formula CO(NH2)2.
This amide has two amino groups (–NH2) joined by a carbonyl functional group (–C(=O)–). It is thus the
simplest amide of carbamic acid.Urea serves an important role in the metabolism of nitrogen-containing
compounds by animals and is the main nitrogen-containing substance in the urine of mammals. Urea is
New Latin, from French urée, from Ancient Greek οὖρον (ouron, “urine”), itself from Proto-Indo-
European *h₂worsom.It is a colorless, odorless solid, highly soluble in water, and practically non-toxic
(LD50 is 15 g/kg for rats).[6] Dissolved in water, it is neither acidic nor alkaline. The body uses it in
many processes, most notably nitrogen excretion. The liver forms it by combining two ammonia molecules
(NH3) with a carbon dioxide (CO2) molecule in the urea cycle. Urea is widely used in fertilizers as a
source of nitrogen (N) and is an important raw material for the chemical industry.In 1828 Friedrich
Wöhler discovered that urea can be produced from inorganic starting materials, which was an important
conceptual milestone in chemistry. This showed for the first time that a substance previously known only
as a byproduct of life could be synthesized in the laboratory without biological starting materials, thereby
contradicting the widely held doctrine of vitalism, which stated that only living organisms could produce
the chemicals of life.37
Keywords: urea, metabolism, non-toxic, excretion, fertilizers, chemicals of life, organic, amino groups,
vitalism.
_____________________________________________________________________________________________________
Introduction
In humans and mammals, almost 80% of the nitrogen excreted is in the form of urea, which is produced
through a series of reactions occurring in the cytosol and mitochondrial matrix of liver cells. 38These
reactions are collectively called the urea cycle or the Krebs-Henseleit cycle.Ammonia is a toxic product of
nitrogen metabolism which should be removed from our body. The urea cycle or ornithine cycle converts
excess ammonia into urea in the mitochondria of liver cells. The urea forms, then enters the blood stream,
is filtered by the kidneys and is ultimately excreted in the urine.1
The overall reaction for urea formation from ammonia is as follows:
2 Ammonia + CO2 + 3ATP - urea + water + 3 ADP
Steps in the Urea Cycle36
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Copyright (c) 2023 Author (s). This is an open-access article distributed under the terms of Creative Commons
Attribution License (CC BY).To view a copy of this license, visit https://creativecommons.org/licenses/by/4.0/
CENTRAL ASIAN JOURNAL OF THEORETICAL AND APPLIED SCIENCES
Volume: 04 Issue: 05 | May 2023, ISSN: 2660-5317
The urea cycle is a series of five reactions catalyzed by several key enzymes. The first two steps in the
cycle take place in the mitochondrial matrix and the rest of the steps take place in the cytosol. Thus the
urea cycle spans two cellular compartments of the liver cell.2
 In the first step of the Krebs-Henseleit cycle, ammonia produced in the mitochondria is converted to
carbamoyl phosphate by an enzyme called carbamoyl phosphate synthetase I. The reaction can be
given as follows:39
NH3 + CO2 + 2ATP → carbamoyl phosphate + 2ADP + Pi
 The second step involves the transfer of a carbamoyl group from carbamoyl phosphate to ornithine to
form citrulline. This step is catalyzed by the enzyme ornithine transcarbamoylase (OTC) . The
reaction is given as follows:35
Carbamoyl phosphate + ornithine → citrulline + Pi
Citrulline thus formed is released into the cytosol for use in the rest of the steps of the cycle.3
 The third step is catalyzed by an enzyme called argininosuccinate synthetase, which uses citrulline
and ATP to form a citrullyl-AMP intermediate, which reacts with an amino group from aspartate to
produce argininosuccinate. This reaction can be given as follows:
Citrulline + ATP + aspartate → argininosuccinate + AMP + Ppi34
 The fourth step involves the cleavage of argininosuccinate to form fumarate and arginine.
Argininosuccinate lyase is the enzyme catalyzing this reaction, which can be represented as follows:40
Argininosuccinate → arginine + fumarate
 In the fifth and last step of the urea cycle, arginine is hydrolyzed to form urea and ornithine. This is
catalyzed by arginase and can be given as follows:33
Arginine → urea + ornithine4
The overall reaction can be given as follows:41
2NH3 + CO2 + 3ATP g urea + 2ADP + AMP + Ppi + 2Pi
Reactions of the urea cycle
Step Reactants Products Catalyzed by Location
1 NH3 + HCO− carbamoyl phosphate + CPS1 mitochondria
3 + 2ATP 2ADP + Pi
2 carbamoyl citrulline + Pi OTC, zinc, mitochondria
phosphate + ornithine biotin
3 citrulline + aspartate + ATP argininosuccinate + AMP + PPi ASS Cytosol32
4 argininosuccinate arginine + fumarate ASL cytosol
5 arginine + H2O ornithine + urea ARG1, cytosol
manganese

Significance of the Urea Cycle

The main purpose of the urea cycle is to eliminate toxic ammonia from the body. About 10 to 20 g of
ammonia is removed from the body of a healthy adult every day. A dysfunctional urea cycle would mean
excess amount of ammonia in the body, which can lead to hyperammonemia and related diseases. 31The
deficiency of one or more of the key enzymes catalyzing various reactions in the urea cycle can cause
disorders related to the cycle. Defects in the urea cycle can cause vomiting, coma and convulsions in new

born babies. This is often misdiagnosed as septicemia and treated with antibiotics in vain. Even 1mm of
excess ammonia can cause severe and irreversible damages.5
Diagnosis of Urea Cycle Defects
A blood aminogram is routinely used in the diagnosis of urea cycle disorders. The concentration of the
nitrogen-carrying amino acids42, glutamine and alanine, in plasma is elevated in the case of OTC
deficiency. In babies, elevated levels of orotic acid in the urine may be an indicator of OTC deficiency.
Increased levels of blood citrulline and argininosuccinate are also seen in cases of citrullinemia.6
In older children, these disorders may present in the form of growth failure, psychomotor retardation and
behavioral abnormalities30. Hence, blood ammonia and urinary orotic acid monitoring and quantitation are
crucial in patients with unexplained neurological symptoms.7
Discussion
Properties
Molecular and crystal structure43
The urea molecule is planar. In solid urea, the oxygen center is engaged in two N–H–O hydrogen bonds.
The resulting dense and energetically favourable hydrogen-bond network is probably established at the
cost of efficient molecular packing: The structure is quite open, the ribbons forming tunnels with square
cross-section. 29The carbon in urea is described as sp2 hybridized, the C-N bonds have significant double
bond character, and the carbonyl oxygen is basic compared to, say, formaldehyde. Urea's high aqueous
solubility reflects its ability to engage in extensive hydrogen bonding with water.8
By virtue of its tendency to form porous frameworks, urea has the ability to trap many organic
compounds. In these so-called clathrates, the organic "guest" molecules are held in channels formed by
interpenetrating helices composed of hydrogen-bonded urea molecules.[7]
As the helices are interconnected, all helices in a crystal must have the same molecular handedness. This
is determined when the crystal is nucleated and can thus be forced by seeding. The resulting crystals have
been used to separate racemic mixtures.[7]
Reactions
Urea is basic. As such it is protonated readily. It is also a Lewis base forming complexes of the
type [M(urea)6]n+.28
Urea reacts with malonic esters to make barbituric acids.9
Decomposition
Molten urea decomposes into ammonium cyanate at about 152 °C, and into ammonia and isocyanic
acid above 160 °C:[8]
CO(NH2)2 → [NH4]+[OCN]− → NH3 + HNCO
Heating above 160 °C yields biuret NH2CONHCONH2 and triuret NH2CONHCONHCONH2 via reaction
with isocyanic acid:[9][8]
CO(NH2)2 + HNCO → NH2CONHCONH2
NH2CONHCONH2 + HNCO → NH2CONHCONHCONH227
At higher temperatures it converts to a range of condensation products, including cyanuric
acid (CNOH)3, guanidine HNC(NH2)2, and melamine.[9][8]

In aqueous solution, urea slowly equilibrates with ammonium cyanate.26 This hydrolysis
cogenerates isocyanic acid, which can carbamylate proteins, in particular the N-terminal amino group and
the side chain amino of lysine, and to a lesser extent the side chains of arginine and cysteine.[10][11] Each
carbamylation event adds 43 daltons to the mass of the protein, which can be observed in protein mass
spectrometery.[11] For this reason, pure urea solutions should be freshly prepared and used, as aged
solutions may develop a significant concentration of cyanate (20 mM in 8 M urea).[11] Dissolving urea in
ultrapure water followed by removing ions (i.e. cyanate) with a mixed-bed ion-exchange resin and storing
that solution at 4 °C is a recommended preparation procedure.[12] However, cyanate will build back up to
significant levels within a few days.[11] Alternatively, adding 25–50 mM ammonium chloride to a
concentrated urea solution decreases formation of cyanate because of the common ion effect.[11][13]
Analysis
Urea is readily quantified by a number of different methods, such as the diacetyl monoxime colorimetric
method, and the Berthelot reaction (after initial conversion of urea to ammonia via urease)25. These
methods are amenable to high throughput instrumentation, such as automated flow injection
analyzers[14] and 96-well micro-plate spectrophotometers.[15]
Ureas describes a class of chemical compounds that share the same functional group, a carbonyl group
attached to two organic amine residues: R1R2N−C(=O)−NR3R4, where R1, R2, R3 and R4 groups
are hydrogen (–H), organyl or other groups. Examples include carbamide peroxide, allantoin, and
hydantoin. Ureas are closely related to biurets and related in structure to
10
amides, carbamates, carbodiimides, and thiocarbamides.
Results
Agriculture
More than 90% of world industrial production of urea is destined for use as a nitrogen-
release fertilizer.[9] Urea has the highest nitrogen content of all solid nitrogenous fertilizers in common
use. Therefore, it has a low transportation cost per unit of nitrogen nutrient. 24The most common impurity
of synthetic urea is biuret, which impairs plant growth.44 Urea breaks down in the soil to give ammonium
ions (NH+4). 23The ammonium is taken up by the plant through its roots. In some soils, the ammonium is
oxidized by bacteria to give nitrate (NO−3), which is also a nitrogen-rich plant nutrient.45 The loss of
nitrogenous compounds to the atmosphere and runoff is wasteful and environmentally damaging so urea
is sometimes modified to enhance the efficiency of its agricultural use. Techniques to make controlled-
release fertilizers that slow the release of nitrogen include the encapsulation of urea in an inert sealant,
and conversion of urea into derivatives such as urea-formaldehyde compounds, which degrade into
ammonia at a pace matching plants' nutritional requirements.11
Resins
Urea is a raw material for the manufacture of urea-formaldehyde resins, used mainly in wood-based
panels such as particleboard, fiberboard and plywood.22
Explosives
Urea can be used to make urea nitrate, a high explosive that is used industrially and as part of
some improvised explosive devices.12
Automobile systems
Urea is used in Selective Non-Catalytic Reduction (SNCR) and Selective Catalytic Reduction
(SCR) reactions to reduce the NOx pollutants in exhaust gases from combustion from diesel, dual fuel,

and lean-burn natural gas engines. The BlueTec system, for example, injects a water-based urea solution
into the exhaust system. Ammonia (NH3) first produced by the hydrolysis of urea reacts with nitrogen
oxides (NOx) and is converted into nitrogen gas (N2) and water within the catalytic converter. The
conversion of noxious NOx to innocuous N2 is described by the following simplified global equation:[16]
4 NO + 4 NH3 + O2 → 4 N2 + 6 H2O
When urea is used, a pre-reaction (hydrolysis) occurs to first convert it to ammonia:
CO(NH2)2 + H2O → 2 NH3 + CO2
Being a solid highly soluble in water (545 g/L at 25 °C),[2] urea is much easier and safer to handle and
store than the more irritant, caustic and hazardous ammonia (NH3), so it is the reactant of choice. Trucks
and cars using these catalytic converters need to carry a supply of diesel exhaust fluid, also sold
as AdBlue, a solution of urea in water.13
Laboratory uses
Urea in concentrations up to 10 M is a powerful protein denaturant as it disrupts the noncovalent bonds in
the proteins. 21This property can be exploited to increase the solubility of some proteins. A mixture of
urea and choline chloride is used as a deep eutectic solvent (DES), a substance similar to ionic liquid.
When used in a deep eutectic solvent, urea gradually denatures the proteins that are solubilized.[17]
Urea can in principle serve as a hydrogen source for subsequent power generation in fuel cells. Urea
present in urine/wastewater can be used directly (though bacteria normally quickly degrade urea).
Producing hydrogen by electrolysis of urea solution occurs at a lower voltage (0.37 V) and thus consumes
less energy than the electrolysis of water (1.2 V).[18]
Urea in concentrations up to 8 M can be used to make fixed brain tissue transparent to visible light while
still preserving fluorescent signals from labeled cells. This allows for much deeper imaging of neuronal
processes than previously obtainable using conventional one photon or two photon confocal
microscopes.[19]
Medical use
Urea-containing creams are used as topical dermatological products to promote rehydration of the skin.
Urea 40% is indicated for psoriasis, xerosis, onychomycosis,20 ichthyosis, eczema, keratosis, keratoderma,
corns, and calluses. If covered by an occlusive dressing, 40% urea preparations may also be used for
nonsurgical debridement of nails. Urea 40% "dissolves the intercellular matrix"[20][21] of the nail plate.
Only diseased or dystrophic nails are removed, as there is no effect on healthy portions of the nail. [22] This
drug (as carbamide peroxide) is also used as an earwax removal aid.[23]
Urea has also been studied as a diuretic. It was first used by Dr. W. Friedrich in 1892.[24] In a 2010 study
of ICU patients, urea was used to treat euvolemic hyponatremia and was found safe, inexpensive, and
simple.[25]
Like saline, urea has been injected into the uterus to induce abortion, although this method is no longer in
widespread use.[26]
The blood urea nitrogen (BUN) test is a measure of the amount of nitrogen in the blood that comes from
urea. It is used as a marker of renal function, though it is inferior to other markers such
as creatinine because blood urea levels are influenced by other factors such as diet, dehydration, [27] and
liver function.19

Urea has also been studied as an excipient in Drug-coated Balloon (DCB) coating formulation to enhance
local drug delivery to stenotic blood vessels.[28][29] Urea, when used as an excipient in small doses
(~3 μg/mm2) to coat DCB surface was found to form crystals that increase drug transfer without adverse
toxic effects on vascular endothelial cells.[30]
Urea labeled with carbon-14 or carbon-13 is used in the urea breath test, which is used to detect the
presence of the bacterium Helicobacter pylori (H. pylori) in the stomach and duodenum of humans,
associated with peptic ulcers. The test detects the characteristic enzyme urease, produced by H. pylori, by
a reaction that produces ammonia from urea. This increases the pH (reduces the acidity) of the stomach
environment around the bacteria. Similar bacteria species to H. pylori can be identified by the same test in
animals such as apes, dogs, and cats (including big cats).14
Miscellaneous uses
 An ingredient in diesel exhaust fluid (DEF), which is 32.5% urea and 67.5% de-ionized water. DEF is
sprayed into the exhaust stream of diesel vehicles to break down dangerous NOx emissions into
harmless nitrogen and water.18
 A component of animal feed, providing a relatively cheap source of nitrogen to promote growth
 A non-corroding alternative to rock salt for road de-icing.[31] It is often the main ingredient of pet
friendly salt substitutes although it is less effective than traditional rock salt or calcium chloride.[32]
 A main ingredient in hair removers such as Nair and Veet15
 A browning agent in factory-produced pretzels
 An ingredient in some skin cream,[33] moisturizers, hair conditioners, and shampoos
 A cloud seeding agent, along with other salts[34]
 A flame-proofing agent, commonly used in dry chemical fire extinguisher charges such as the urea-
potassium bicarbonate mixture
 An ingredient in many tooth whitening products
 An ingredient in dish soap16
 Along with diammonium phosphate, as a yeast nutrient, for fermentation of sugars into ethanol
 A nutrient used by plankton in ocean nourishment experiments for geoengineering purposes
 As an additive to extend the working temperature and open time of hide glue
 As a solubility-enhancing and moisture-retaining additive to dye baths for textile dyeing or printing[35]
 As an optical parametric oscillator in nonlinear optics[36][37]
Conclusions
Urea can be irritating to skin, eyes, and the respiratory tract. Repeated or prolonged contact with urea in
fertilizer form on the skin may cause dermatitis.[44]High concentrations in the blood can be damaging.46
Ingestion of low concentrations of urea, such as are found in typical human urine, are not dangerous with
additional water ingestion within a reasonable time-frame. Many animals (e.g. camels, rodents or dogs)
have a much more concentrated urine which may contain a higher urea amount than normal human
urine17.Urea can cause algal blooms to produce toxins, and its presence in the runoff from fertilized land
may play a role in the increase of toxic blooms.[45]The substance decomposes on heating above melting

point, producing toxic gases, and reacts violently with strong oxidants, nitrites, inorganic chlorides,
chlorites and perchlorates, causing fire and explosion.[46]
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CENTRAL ASIAN JOURNAL OF THEORETICAL

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Urea Cycle, Properties and Applications of Urea

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Significance of the Urea Cycle

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