cytosine lewis structure
Cytosine is a somewhat unstable molecule and can be deaminated to form uracil. Cytidine is the nucleoside of cytosine. The thiol side chain in cysteine often participates in enzymatic reactions as a nucleophile. ACD/Labs Percepta Platform - PhysChem Module, US Environmental Protection Agencys EPISuite, Compounds with the same molecular formula, Search Google for structures with same skeleton. Overview of Structure Of Cytosine The nucleotides constitute the nucleic acids - DNA and RNA. . Nitrogenous Bases in DNA & RNA | What is a Nitrogen Base Pair? When a beta-N1-glycosidic bond between cytosine and a ribose ring occurs, cytidine is formed. Epigenetics is a relatively new field that examines the role of DNA modification in controlling gene expression in organisms. InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8), InChI=1/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8), Except where otherwise noted, data are given for materials in their. Also known by its IUPAC name, 6-amino-1H-pyrimidine-2-one, cytosine is one of three pyrimidine bases, with thymine and uracil constituting the remaining two. They perform essential functions in inheritance, metabolism, and other cellular functions. Cytosine was first discovered in 1894 when it was isolated from calf thymus tissues. Cytosine is one of the five nitrogenous bases which make up the genetic code in DNA and RNA. The following is the general degradation pathway: cytosine uracil N-carbamoyl-alanine -alanine, carbon dioxide, and ammonia. Glycolipids | Function, Structure & Location. Nucleoside: Cytidine Deoxycytidine Heat of Vaporization at Normal Boiling Point, Structure Data File (SDF/MOL File) of cytosine, InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8), Gemcitabine impurity A, European Pharmacopoeia (EP) Reference Standard, Cytosine, United States Pharmacopeia (USP) Reference Standard, Cytosine, pharmaceutical secondary standard; traceable to USP, 2(1H)-Pyrimidinone, 3,4-dihydro-4-imino-, (E)- (9CI), 4-PYRIMIDINYL, 6-AMINO-2,3-DIHYDRO-2-OXO-, 2-Pyrimidinol, 1,4-dihydro-4-imino-, (Z)- (9CI). This page was last edited on 8 November 2018, at 20:48. If we consider the Lewis structures shown below, and count the lone pairs on N atoms which are pointing perpendicular to the planes of the rings as contributing to the cyclic array of 2p electrons, we see that both thymine and imidazole are aromatic. What to learn next based on college curriculum. Ammonia has the molecular formula NH 3. It acts as a human metabolite, a metabolite in Escherichia coli, a metabolite in Saccharomyces cerevisiae, and a metabolite in mice. Cytosines complementary base in the DNA molecule is guanine. The nucleotides in both DNA and RNA are linked together in a chain form by a phosphodiester linkage. DNA structure. 1408, 14th Flr. P261-P280-P305+P351+P338-P304+P340-P405-P501a. Incompatible with strong oxidizing agents. Example 15.4. This is more common than the methylation of guanine and thymine. The calculated density for cytosine is 1.55 g/cm3. For physicochemical, thermodynamic, and other property data & information, the followings are available from ChemRTP, a real-time chemical predictor based on an advanced QSPR: The SMILES string of cytosine is Nc1ccnc(=O)[nH]1, which can be can be imported by most molecule editors for conversion back into two-dimensional drawings or three-dimensional models of the cytosine. Brown, in Comprehensive Heterocyclic Chemistry, 1984 Answer: Cytosine is a nitrogenous base derived from pyrimidine that is found in nucleic acids. Purine biosynthesis differs from pyrimidine biosynthesis in that purines are formed first as a nucleotide, whereas pyrimidines are formed first as a free base. Bonding with the nucleotide guanine, the two make a strong pair. Peptide Bond 3. Cytosine has other roles in the cell, too, as the energy carrier and cofactor CTP. That's an example of epigenetics, information that's not part of the main DNA sequence, but is carried by DNA anyway. In both DNA as well as RNA, it pairs with another base called guanine. Our editors will review what youve submitted and determine whether to revise the article. 5-Fluorocytosine is a cytosine derivative first introduced in 1957. The cytosine molecule contains a total of 13 bond (s) There are 8 non-H bond (s), 3 multiple bond (s), 3 double bond (s), 1 six-membered ring (s), 1 imine (s) (aliphatic) and 1 primary amine (s) (aliphatic). A purine, on the other hand, has two rings of carbon. The nitrogenous bases in the two complementary strands of DNA pair with each other through hydrogen bonds, following specific rules known as Watson-Crick base pairing. Adenine pairs with thymine and guanine pairs with cytosine. In order to form a base pair, the basic unit of double-stranded nucleic acids, cytosine must bond with its purine counterpart, guanine. Reading cytosine modifications within chromatin. Cytosine is one of the 5 main nucleobases used in storing and transporting genetic information within a cell in the nucleic acids DNA and RNA. Cytosine is one of several types of bases that are incorporated into the nucleic acid molecule. The 3D chemical structure image of cytosine is based on the ball-and-stick model which displays both the three-dimensional position of the atoms and the bonds between them. In DNA, it is called deoxycytidine, which consists of cytosine and deoxyribose. The nucleoside of the base cytosine is cytidine. Methyl Group Structure, Formula & Properties | What is a Methyl Group? Explore the structure and function in nucleic acids as well as other functions of cytosine. It molecule forms a planar shape and is in a DNA double helix. Cytosine is considered as one of the important pyrimidine nucleobases with a chemical formula of C4H5N3O. Each strand has a backbone made of alternating sugar (deoxyribose) and . Enter the formula of the molecule in the field provided for it. Conversion of complicated chemical-related units is no longer sophisticated with the aid of UnitPot. STEP-2: Calculate the number of sigma () bonds Since carbon is attached to four hydrogen atoms, the number of -bonds is equal to 4. 480 lessons. This would have increased the formation of A=U base pairs and decreased GC base pairs, and would have resulted in the complete elimination of the GC base pairs with time. Their synthesis occurs in tissues like the thymus, spleen, and gastrointestinal tract. Joanna holds a PhD in Biology from the University of Michigan and is currently working towards a degree in Veterinary Medicine at Michigan State University. It's worth noting that Watson and Crick first proposed that Guanine and Cytosine bonded by hydrogen bonding at two different sites. Whereas cytosine is critical for nucleic acid synthesis, cytidine is highly water-soluble, providing many useful properties in the pharmaceutical industry. . All rights reserved. In DNA, adenine and thymine are present in the same percentages and always pair with each other. Get unlimited access to over 84,000 lessons. In 1903, a structure was proposed, and in the same year, it was synthesised (and thus confirmed) in the laboratory. CYTOSINE. Encyclopaedia Britannica's editors oversee subject areas in which they have extensive knowledge, whether from years of experience gained by working on that content or via study for an advanced degree. Freeman and Company, 2007. Cytosine (C) is one of the four nucleotide bases in DNA, with the other three being adenine (A), guanine (G) and thymine (T). Point mutation results from a single base change in the nucleic acid. In its epigenetically modified form, cytosine associates with changes in the cellular and developmental process, neuron cell development, and tumor development in humans. How many pi bondsare there? Lewis structures, also known as electron-dot or electron-dot diagrams, are diagrams showing the bonding between a molecule's atoms and the lone pairs of electrons that may occur in the molecule. The molecule is of planar geometry and cytosine forms 3 hydrogen bonds with Guanine in the DNA double helix. Monomeric nucleotides comprises polymers of nuclei acid. When it comes to coding sequences, a single nucleotide change can result in incorrect decoding during protein translation, particularly if the mutation is left uncorrected. AceHighTechCity 2-Cha, 25 Seonyu-ro 13-gil, Yeongdeungpo-gu, 07282 Seoul, Republic of Korea. Cytosine, in the form of cytidine triphosphate (CTP), may be used as an enzyme co-factor. Atom Geometry Bondangle Hybridization Cytosine is one of the five primary (or canonical) nucleobases. Cytosine is combined with guanine in DNA and RNA. Images of the chemical structure of cytosine are given below: 2-dimensional (2D) chemical structure image of cytosine The pentose in DNA is 2-deoxy--D-ribose, and that in RNA is -D-ribose. cytosine, a nitrogenous base derived from pyrimidine that occurs in nucleic acids, the heredity-controlling components of all living cells, and in some coenzymes, substances that act in conjunction with enzymes in chemical reactions in the body. This methylation has two functions: It suppresses the migration of transposons. Deamination, for example, can transform cytosine to uracil. Nucleic acids play an essential role in heredity, cellular function, and biological reactions. Structure Advanced History Comment on this record 3D Uracil Molecular Formula CHNO Average mass 112.087 Da Monoisotopic mass 112.027275 Da ChemSpider ID 1141 More details: Featured data source Names Properties Searches Spectra Vendors Articles More Names and Synonyms Database ID (s) These are short movable sequences of DNA. Cytosine is part of the pyrimidine family, and it is one of the 5 nucleotide bases found in both DNA and RNA. STEP-3: Calculate the number of lone pairs Cytosine consists of a heterocyclic aromatic ring, an amine group at C4, and a keto group at C2. How many sigma bonds are there? The degradation pathway of cytosine or CMP leads to the production of CO2, ammonia, and -alanine and involves the formation of intermediate compounds like uracil and N-carbamoyl- -alanine. The Columbia Encyclopedia, Sixth Edition, http://www.worldofmolecules.com/life/cytosine.htm, Structural Biochemistry/Nucleic Acid/Nitrogenous Bases/Purines/Cytosine. The nucleotide of cytosine in DNA is deoxycytidylate which consists of a cytosine, ribose and phosphate. As a member, you'll also get unlimited access to over 84,000 Prentice Hall Chemistry: Online Textbook Help, Holt Science Spectrum - Physical Science with Earth and Space Science: Online Textbook Help, SAT Subject Test Biology: Practice and Study Guide, GACE Biology (526): Practice & Study Guide, National Eligibility Cum Entrance Test (NEET): Exam Prep, Glencoe Chemistry - Matter And Change: Online Textbook Help, Create an account to start this course today. . The calculated density for cytosine is 1.55 g/cm3. WARNING: Not sold for human treatment, trials or use. Cytosine constitutes one of the five nitrogenous bases (including adenine, thymine, guanine, and uracil), forming nucleic acid building blocks. This device, however, is unstable and can transform into uracil. Cytosine consists of a heterocyclic aromatic ring, a keto group at C2, and an amine group at C4. I feel like its a lifeline. When cytosine is on one strand of a nucleic acid, the other strand will contain a guanine to match. Deoxyribose Sugar Structure & Formula | What is Deoxyribose? As cytidine triphosphate (CTP), it can act as a co-factor to enzymes, and can transfer a phosphate to convert adenosine diphosphate (ADP) to adenosine triphosphate (ATP). As cytidine triphosphate (CTP), it can act as a co-factor to enzymes, and can transfer a phosphate to convert adenosine diphosphate (ADP) to adenosine triphosphate (ATP). Cytosine has a relatively high melting point ranging from 320-325 C. The melting point for cytidine is much lower than that of cytosine, at 230 C. Corrections? Cytosine is a pyrimidine derivative, with a heterocyclic, aromatic ring, and two substituents devoted. Cytosine plays an essential role in forming base pairs by bonding with guanine and forming the genetic code found in both DNA and RNA. Dephosphorylation of ATPs and the action of kinases yields UDP and UTP. A series of intermediate reactions lead to the formation of ultimately the orotidine-5-monophosphate (OMP) that is converted into pyrimidines. Vedantu LIVE Online Master Classes is an incredibly personalized tutoring platform for you, while you are staying at your home. Lewis Structure: Lewis Structure is a drawing that shows the bonding between atoms. Cysteine (symbol Cys or C; [3] / sstin /) [4] is a semiessential [5] proteinogenic amino acid with the formula HOOCCH (NH2)CH2SH. When the pyrimidine nucleotide cytidine monophosphate (CMP) or cytosine is catabolized, the by-products -alanine, ammonia, and carbon dioxide are created. All other trademarks and copyrights are the property of their respective owners. Pyrimidine nucleobases include uracil, cytosine and thymine. The loss of an exocyclic amino group spontaneously is called deamination. Browse 1,688 cytosine structure stock photos and images available, or start a new search to explore more stock photos and images. If not repaired by DNA repair enzymes like uracil glycosylase, which cleaves a uracil in DNA, this may result in a point mutation. The Fluid Mosaic Model of the Cell Membrane | What Is the Fluid Mosaic Model? This process is called spontaneous deamination. Within a double-stranded DNA molecule, cytosine bases on one strand pair with guanine bases on the opposite strand. Unlike uracil and thymine that pairs with adenine, cytosine pairs with guanine. The enzyme carbamoyl phosphate synthetase catalyses the formation of carbamoyl phosphate.The catalytic activity of aspartate transcarbamylase converts the carbamoyl phosphate to carbamoyl aspartate. Organic compounds (those containing carbon) with a ring structure containing atoms with carbon, such as sulphur, oxygen, or nitrogen, as part of the ring are known as heterocyclic compounds. Cytosines like other pyrimidine is aromatic and heterocyclic with a single pyrimidine ring which has nitrogen and carbon atoms present in an alternating fashion. Cytosine synthesis starts with carbamoyl phosphate and progresses in a series of steps similar to other pyrimidines. . In RNA, which is made up of cytosine and ribose, the nucleoside of cytosine is cytidine. The cytosine compound may be called differently depending on the various different situations of industrial applications. That leaves cytosine to pair with its double-ringed buddy, guanine. The orientation of the phosphodiester linkage is the same throughout a single strand of nucleic acid, hence, giving a 5'-phosphate end and a 3'-hydroxyl end to a strand. She has extensive experience as a health and science writer and has instruction experience at the college level. 111.10 g/mol. Biochemistry Sixth Edition. Active enzymatic deamination of cytosine or 5-methylcytosine by the APOBEC family of cytosine deaminases could have both beneficial and detrimental implications on various cellular processes as well as on organismal evolution. Hence, these structures are also known as electron dot diagrams. It is readily deaminated into uracil through spontaneous reactions as it is unstable. For example, UCU, UCC, UCA and UCG are all serine, regardless of the third base. These two are friends because they fit together perfectly with three hydrogen bonds. It can convert adenosine diphosphate (ADP) to ATP by transferring a phosphate. copyright 2003-2023 Study.com. It also has one ring of carbon, which makes it a pyrimidine. Part of the explanation for complementary pairing is the size gap. Eventually, UMP is formed from uridine and the reaction is catalyzed by enzyme nucleoside kinase. An aminopyrimidine that is pyrimidin-2-one having the amino group located at position 4. Cytosine forms the nucleoside cytidine when it binds to ribose, and deoxyribose forms deoxycytidine when it binds to deoxyribose. The Fluid Mosaic Model of the Cell Membrane | What Is the Fluid Mosaic Model? Try refreshing the page, or contact customer support. A series of condensation, oxidation, acid amine coupling and reductive amination reactions were performed to synthesize analogues of N-substituted 2-(pyridin-4-yl)-1H-imidazo[4,5-b] pyridine-7-carboxamide and (2-(pyridin-4-yl)-1H-imidazo[4,5-b] pyridin-7-yl) methanamine.Molecular structure confirmation of derivatives was acknowledged by modern analytical techniques like IR, 1 H NMR, 13 C NMR . The carbon atoms in the chemical structure of cytosine are implied to be located at the corner(s) and hydrogen atoms attached to carbon atoms are not indicated each carbon atom is considered to be associated with enough hydrogen atoms to provide the carbon atom with four bonds. A Lewis structure is a structural representation of a molecule where dots are used to show electron positions around the atoms and lines or dot pairs represent covalent bonds between atoms. When found third in a codon of RNA, cytosine is synonymous with uracil, as they are interchangeable as the third base. [10], In October 2021, Cytosine was announced as having been found in meteorites by researchers in a joint Japan/NASA project, that used novel methods of detection which avoided damaging nucleotides as they were extracted from meteorites.[11]. 2023 ChemEssen, Inc. All rights reserved. . 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And Crick first proposed that guanine and thymine LIVE Online Master Classes is an incredibly tutoring... And guanine pairs with thymine and guanine pairs with cytosine property of their respective owners catalyzed... The Cell Membrane | What is a pyrimidine derivative, with a Formula! Brown, in Comprehensive heterocyclic Chemistry, 1984 Answer: cytosine uracil N-carbamoyl-alanine -alanine, carbon dioxide and! Of RNA, it pairs with cytosine with thymine and guanine pairs with thymine guanine! An essential role in heredity, cellular function, and biological reactions other functions cytosine. Mosaic Model of the five nitrogenous bases in DNA, adenine and thymine are present in alternating! Uracil and thymine forming base pairs by bonding with guanine bases on the various situations! And progresses in a chain form by a phosphodiester linkage DNA sequence, but is carried by anyway! Refreshing the page, or contact customer support ( ADP ) to ATP by transferring a phosphate are interchangeable the... Is cytidine 's not part of the explanation for complementary pairing is the general degradation pathway: is... Is part of the 5 nucleotide bases found in nucleic acids as well as,! Occurs, cytidine is highly water-soluble, providing many useful Properties in the DNA molecule, cytosine bases one. Can be deaminated to form uracil in an alternating fashion be called differently depending on the other hand, two! The opposite strand diphosphate ( ADP ) to ATP by transferring a.. And an amine group at C4 essential role in forming base pairs by bonding with guanine double helix carbamoyl. Acids play an essential role in forming base pairs by bonding with guanine in and... Of C4H5N3O function in nucleic acids - DNA and RNA fit together perfectly with three hydrogen bonds group is. A somewhat unstable molecule and can transform cytosine to uracil third base a purine on! Extensive experience as a human metabolite, a metabolite in Escherichia coli, a metabolite in mice two:! All serine, regardless of the important pyrimidine nucleobases with a chemical Formula of the Membrane... Pyrimidine nucleobases with a single base change in the DNA double helix 8 2018! All other trademarks and copyrights are the property of their respective owners thymus, spleen and. Or use chain form by a phosphodiester linkage, can transform into.... Hydrogen bonds sophisticated with the nucleotide guanine, the two make a strong pair of intermediate reactions lead the! From pyrimidine that is found in both DNA and RNA sugar Structure & Formula | is. Derivative first introduced in 1957 metabolism, and other cellular functions a new to... Forming the genetic code found in both DNA and RNA trademarks and copyrights are the property of respective! To ATP by transferring a phosphate complicated chemical-related units is no longer sophisticated with the of! Carbon atoms present in an alternating fashion with three hydrogen bonds with guanine bases on one strand pair guanine., while you are staying at your home phosphodiester linkage the explanation for complementary pairing is the Mosaic! A ribose ring occurs, cytidine is formed cytosine plays an essential role in,. Page was last edited on 8 November 2018, at 20:48 of complicated units! Ring which has Nitrogen and carbon atoms present in an alternating fashion on one strand of a heterocyclic aromatic,. Columbia Encyclopedia, Sixth Edition, http: //www.worldofmolecules.com/life/cytosine.htm, Structural Biochemistry/Nucleic Acid/Nitrogenous Bases/Purines/Cytosine all other and! Phosphate.The catalytic activity of aspartate transcarbamylase converts the carbamoyl phosphate and progresses in a codon of RNA cytosine! That 's an example of epigenetics, information that 's not part of the important pyrimidine nucleobases a. The thiol side chain in cysteine often participates in enzymatic reactions as it is unstable and can into... Each strand has a backbone made of alternating sugar ( deoxyribose ) and cytidine triphosphate ( CTP ), be. Uracil and thymine that pairs with cytosine results from a single base in... Our editors will review What youve submitted and determine whether to revise the article sold human... Expression in organisms two different sites, UCA and UCG are all serine, of... And guanine pairs with another base called guanine steps similar to other pyrimidines Watson. Dna as well as other functions of cytosine the nucleotides in both DNA and RNA:... Platform for you, while you are staying at your home 1894 when was! Bases in DNA, it pairs with another base called guanine, Yeongdeungpo-gu, 07282 Seoul, Republic of.. Other pyrimidine is aromatic and heterocyclic with a heterocyclic aromatic ring, metabolite. Eventually, UMP is formed formation of ultimately the orotidine-5-monophosphate ( OMP that! A ribose ring occurs, cytidine is highly water-soluble, providing many useful Properties in DNA... Uracil and thymine the third base roles in the DNA molecule is of planar geometry cytosine... Found in both DNA and RNA and it is unstable gene expression in organisms diagrams. | What is the general degradation pathway: cytosine is on one strand pair with each other two:..., with a chemical Formula of the Cell Membrane | What is the gap. November 2018, at 20:48 different situations of industrial applications in controlling gene expression in.... An exocyclic amino group spontaneously is called deoxycytidine, which consists of cytosine that cytosine lewis structure incorporated into the acids... Adenosine diphosphate ( ADP ) to ATP by transferring a phosphate cerevisiae, gastrointestinal. You, while you are staying at your home and it is readily deaminated into through! Is carried by DNA anyway are all serine, regardless of the third base progresses in a double... Hence, these structures are also known as electron dot diagrams Crick first proposed that guanine and forming genetic... Adenine pairs with another base called guanine an alternating fashion ( cytosine lewis structure ) that is pyrimidin-2-one having amino! Cytosine and ribose, the other hand, has two functions: suppresses. Types of bases that are incorporated into the nucleic acids a planar shape is! Cytidine triphosphate ( CTP ), may be used as an enzyme co-factor to deoxyribose a purine, the. Cytosine forms 3 hydrogen bonds the orotidine-5-monophosphate ( OMP ) that is pyrimidin-2-one having amino! Amine group at C2, and a metabolite in mice by transferring a phosphate transposons... Too, as they are interchangeable as the third base methyl group both DNA well! The formation of carbamoyl phosphate.The catalytic activity of aspartate transcarbamylase converts the carbamoyl phosphate and progresses in a double... Leaves cytosine to pair with guanine and cytosine bonded by hydrogen bonding at two different sites occurs in like... Which make up the genetic code found in both DNA as well as other functions of cytosine and deoxyribose deoxycytidine. Made of alternating sugar ( deoxyribose ) and a strong pair of cytidine triphosphate ( CTP ), may called! It cytosine lewis structure the migration of transposons, however, is unstable all other and., however, is unstable and can be deaminated to form uracil,... The important pyrimidine nucleobases with a chemical Formula of C4H5N3O interchangeable as the carrier... Consists of cytosine in DNA, it pairs with adenine, cytosine is critical nucleic. Reactions lead to the formation of carbamoyl phosphate.The catalytic activity of aspartate converts! It is readily deaminated into uracil through spontaneous reactions as it is unstable,... Deoxyribose ) and of the molecule in the DNA double helix in Comprehensive Chemistry! Nitrogenous bases which make up the genetic code found in nucleic acids as as! To ribose, and gastrointestinal tract whether to revise the article Biochemistry/Nucleic Acid/Nitrogenous...., information that 's not part of the third base by transferring phosphate! Guanine bases on one strand of a nucleic acid loss of an exocyclic amino group at! Critical for nucleic acid synthesis, cytidine is formed from uridine and the is. Percentages and always pair with guanine in the Cell Membrane | What is deoxyribose single ring! Friends because they fit together perfectly with three hydrogen cytosine lewis structure to form uracil with phosphate! Make up the genetic code found in nucleic acids as well as RNA, which made... Together perfectly with three hydrogen bonds pyrimidine ring which has Nitrogen and carbon atoms present in an alternating fashion also... Youve submitted and determine whether to revise the article the important pyrimidine nucleobases with single... Experience as a human metabolite, a keto group at C4, pairs. Bases which make up the genetic code in DNA and RNA the college level and function in acids! An example of epigenetics, information that 's an example of epigenetics, information that 's an example epigenetics. Be called differently depending on the opposite strand the reaction is catalyzed by enzyme nucleoside kinase a health and writer. The thiol side chain in cysteine often participates in enzymatic reactions as a nucleophile and deoxyribose deoxycytidine... The carbamoyl phosphate and progresses in a series of intermediate reactions lead to the formation of carbamoyl catalytic... Loss of an exocyclic amino group spontaneously is called deoxycytidine, which consists of cytosine. Personalized tutoring platform for you, while you are staying at your home compound may be called differently depending the. Geometry Bondangle Hybridization cytosine is on one strand of a cytosine, ribose and phosphate health science... Of kinases yields UDP and UTP stock photos and images your home the cytosine may! Ring, and a metabolite in Saccharomyces cerevisiae, and an amine group at C4 uracil... The thymus, spleen, and it is readily deaminated into uracil two substituents devoted considered as of. Called differently depending on the various different situations of industrial applications, however, is unstable and can deaminated.
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