词条 | Aspartic acid |
释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464371725 | Name = Aspartic acid | ImageFile = L-Asparaginsäure - L-Aspartic acid.svg | ImageAlt = | ImageFile1 = L-Aspartic acid zwitterion ball from xtal.png | ImageSize1 = 210 | ImageAlt1 = Ball-and-stick model of the L-aspartic acid molecule as a zwitterion | IUPACName = {{ubl | Trivial: Aspartic acid | Systematic: Aminobutanedioic acid }} | OtherNames = {{ubl | Aminosuccinic acid | Asparagic acid | Asparaginic acid[1] }} |Section1={{Chembox Identifiers | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 28XF4669EP | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 139661 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C16433 | InChI = 1/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9) | InChIKey = CKLJMWTZIZZHCS-UHFFFAOYAE | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = CKLJMWTZIZZHCS-UHFFFAOYSA-N | CASNo = 617-45-8 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo2_Ref = {{cascite|changed|??}} | CASNo2 = 56-84-8 | CASNo2_Comment = (L-isomer) | CASNo3_Ref = {{cascite|changed|??}} | CASNo3 = 1783-96-6 | CASNo3_Comment = (D-isomer) | EC_number = 200-291-6 | PubChem = 424 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 411 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 22660 | SMILES = O=C(O)CC(N)C(=O)O | SMILES1 = O=C(O)CC([NH3+])C(=O)[O-] | SMILES1_Comment = Zwitterion | SMILES2 = O=C([O-])CC([NH3+])C(=O)[O-] | SMILES2_Comment = Deprotonated zwitterion (aspartate) | SMILES3 = C(C(C(=O)O)N)C(=O)O | SMILES4 = C(C(C(=O)[O-])[NH3+])C(=O)O | SMILES4_Comment = Zwitterion | SMILES5 = C(C(C(=O)[O-])[NH3+])C(=O)[O-] | SMILES5_Comment = Deprotonated zwitterion (aspartate) }} |Section2={{Chembox Properties | C=4 | H=7 | N=1 | O=4 | Appearance = colourless crystals | Density = 1.7 g/cm3 | MeltingPtC = 270 | MeltingPt_notes = | BoilingPtC = 324 | BoilingPt_notes = (decomposes) | Solubility = 4.5 g/L[2] | ConjugateBase = Aspartate | pKa = {{ubl | 1.99 (α-carboxyl; H2O) | 3.90 (side chain; H2O) | 9.90 (amino; H2O)[3] }} | MagSus = -64.2·10−6 cm3/mol |Section7={{Chembox Hazards | NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 0 | FlashPt = | AutoignitionPt = }} Aspartic acid (symbol Asp or D;[4] the ionic form is known as aspartate), is an α-amino acid that is used in the biosynthesis of proteins.[5] Similar to all other amino acids it contains an amino group and a carboxylic acid. Its α-amino group is in the protonated –NH{{su|b=3|p=+}} form under physiological conditions, while its α-carboxylic acid group is deprotonated −COO− under physiological conditions. Aspartic acid has an acidic side chain (CH2COOH) which reacts with other amino acids, enzymes and proteins in the body.[5] Under physiological conditions (pH 7.4) in proteins the side chain usually occurs as the negatively charged aspartate form, −COO−.[5] It is a non-essential amino acid in humans, meaning the body can synthesize it as needed. It is encoded by all the codons GAU and GAC. D-Aspartate is one of two D-amino acids commonly found in mammals.[3] In proteins aspartate sidechains are often hydrogen bonded to form asx turns or asx motifs, which frequently occur at the N-termini of alpha helices. The L-isomer of Asp is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. Aspartic acid, like glutamic acid, is classified as an acidic amino acid, with a pKa of 3.9, however in a peptide this is highly dependent on the local environment, and could be as high as 14. Asp is pervasive in biosynthesis. DiscoveryAspartic acid was first discovered in 1827 by Auguste-Arthur Plisson and Étienne Ossian Henry[6] by hydrolysis of asparagine, which had been isolated from asparagus juice in 1806.[7] Their original method used lead hydroxide, but various other acids or bases are more commonly used instead. Forms and nomenclatureThere are two forms or enantiomers of aspartic acid. The name "aspartic acid" can refer to either enantiomer or a mixture of two.[8] Of these two forms, only one, "L-aspartic acid", is directly incorporated into proteins. The biological roles of its counterpart, "D-aspartic acid" are more limited. Where enzymatic synthesis will produce one or the other, most chemical syntheses will produce both forms, "DL-aspartic acid", known as a racemic mixture. BiosynthesisBecause Aspartate can be synthesized by the body it is classified as a non-essential amino acid. In the human body, aspartate is most frequently synthesized through the transamination of oxaloacetate. The biosynthesis of aspartate is facilitated by an aminotransferase enzyme: the transfer of an amine group from another molecule such as alanine or glutamine yields aspartate and an alpha-keto acid.[5] Aspartate also plays an important role in the urea cycle. Chemical synthesisRacemic aspartic acid can be synthesized from diethyl sodium phthalimidomalonate, (C6H4(CO)2NC(CO2Et)2).[9] The major disadvantage of the above technique is that equimolar amounts of each enantiomer are made. Using biotechnology it is now possible to use immobilised enzymes to create just one type of enantiomer owing to their stereospecificity. MetabolismIn plants and microorganisms, aspartate is the precursor to several amino acids, including four that are essential for humans: methionine, threonine, isoleucine, and lysine. The conversion of aspartate to these other amino acids begins with reduction of aspartate to its "semialdehyde", O2CCH(NH2)CH2CHO.[10] Asparagine is derived from aspartate via transamidation: -O2CCH(NH2)CH2CO2- + GC(O)NH3+ O2CCH(NH2)CH2CONH3+ + GC(O)O (where GC(O)NH2 and GC(O)OH are glutamine and glutamic acid, respectively) Participation in the urea cycleIn the urea cycle, aspartate and ammonia donate amino groups leading to the formation of urea. Other biochemical rolesAspartate has many other biochemical roles. It is a metabolite in the urea cycle and participates in gluconeogenesis. It carries reducing equivalents in the malate-aspartate shuttle, which utilizes the ready interconversion of aspartate and oxaloacetate, which is the oxidized (dehydrogenated) derivative of malic acid. Aspartate donates one nitrogen atom in the biosynthesis of inosine, the precursor to the purine bases. In addition, aspartic acid acts as a hydrogen acceptor in a chain of ATP synthase. Interactive pathway map{{GlycolysisGluconeogenesis_WP534|highlight=Aspartic_acid__alt1}}NeurotransmitterAspartate (the conjugate base of aspartic acid) stimulates NMDA receptors, though not as strongly as the amino acid neurotransmitter L-glutamate does.[11] Applications & marketAs of 2014, the global market for aspartic acid is $117MM annually (50-60K MT/Yr)[12] with potential areas of growth accounting for an {{clarify|text=addressable market|reason=Is this Total addressable market or Serviceable available market?|date=March 2017}} of $8.78BB.[13] The three largest market segments include the U.S., Western Europe, and China. Current applications include biodegradable polymers (polyaspartic acid), low calorie sweeteners (aspartame), scale and corrosion inhibitors, and resins. Nearly all aspartic acid is manufactured in China. Superabsorbent polymersOne area of aspartic acid market growth is biodegradable superabsorbent polymers (SAP).{{synthesis inline|date=March 2017}} The superabsorbent polymers market is anticipated to grow at a CAGR{{clarify|date=March 2017}} of 5.5% from 2014 to 2019 to reach a value of $8.78BB globally.[13] Around 75% of superabsorbent polymers are used in disposable diapers and an additional 20% is used for adult incontinence and feminine hygiene products. Polyaspartic acid, the polymerization product of aspartic acid, is a biodegradable substitute to polyacrylate.[14] The polyaspartate market comprises a small fraction (est. < 1%) of the total SAP market. Additional usesIn addition to SAP, aspartic acid has applications in the $19B fertilizer industry, where polyaspartate improves water retention and nitrogen uptake;[15] the $1.1B (2020) concrete floor coatings market, where polyaspartic is a low VOC, low energy alternative to traditional epoxy resins;[16] and lastly the >$5B scale and corrosion inhibitors market.[17] SourcesDietary sourcesAspartic acid is not an essential amino acid, which means that it can be synthesized from central metabolic pathway intermediates in humans. However, aspartic acid is found in:
See also
References1. ^1 {{cite book |title= The Merck Index |chapter= 862. Aspartic acid |edition= 11th |page= 132 |year= 1989 |isbn= 978-0-911910-28-5}} 2. ^{{cite web|url=http://www.inchem.org/documents/icsc/icsc/eics1439.htm|title=ICSC 1439 - L-ASPARTIC ACID|website=inchem.org}} 3. ^{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = CRC Press | isbn = 978-1498754286 | page=5–89 | title-link = CRC Handbook of Chemistry and Physics }} 4. ^{{cite web| url = http://www.chem.qmul.ac.uk/iupac/AminoAcid/AA1n2.html | title = Nomenclature and Symbolism for Amino Acids and Peptides | publisher = IUPAC-IUB Joint Commission on Biochemical Nomenclature | year = 1983 | accessdate = 5 March 2018| archiveurl= https://web.archive.org/web/20081009023202/http://www.chem.qmul.ac.uk/iupac/AminoAcid/AA1n2.html| archivedate= 9 October 2008 | deadurl= no}} 5. ^1 2 3 {{Cite book|url=https://www.worldcat.org/oclc/910538334|title=Fundamentals of biochemistry : life at the molecular level|last=G.,|first=Voet, Judith|last2=W.,|first2=Pratt, Charlotte|isbn=9781118918401|oclc=910538334|date=2016-02-29}} 6. ^{{cite book | title = Traité de chimie | volume = 3 | author1-first = Jöns Jakob | author1-last = Berzelius | author1-link = Jöns Jacob Berzelius | author2-first = Olof Gustaf | author2-last = Öngren | name-list-format = vanc | year = 1839 | language = French | publisher = A. Wahlen et Cie.| publication-place = Brussels | page = 81 | url = https://books.google.com/books?id=szLPAAAAMAAJ | accessdate = 25 August 2015 }} 7. ^{{cite book | first = R.H.A. | last = Plimmer | editor-first1 = R.H.A. | editor-last1 = Plimmer | editor-first2 = F.G. | editor-last2 = Hopkins | name-list-format = vanc | title = The chemical composition of the proteins | url = https://books.google.com/?id=7JM8AAAAIAAJ&pg=PA112 |accessdate = January 18, 2010 | edition = 2nd | series = Monographs on Biochemistry | volume = Part I. Analysis | origyear = 1908 | year = 1912 | publisher = Longmans, Green and Co. | location = London | page = 112 }} 8. ^{{IUPAC-IUB amino acids 1983}}. 9. ^{{OrgSynth|last1=Dunn|first1=M. S.|last2=Smart|first2=B. W.|name-list-format=vanc|title=DL-Aspartic Acid|prep=CV4P0055|volume=30|pages=7|year=1950|collvol=4|collvolpages=55}}. 10. ^{{Lehninger3rd|name-list-format = vanc }} 11. ^{{cite journal | vauthors = Chen PE, Geballe MT, Stansfeld PJ, Johnston AR, Yuan H, Jacob AL, Snyder JP, Traynelis SF, Wyllie DJ | title = Structural features of the glutamate binding site in recombinant NR1/NR2A N-methyl-D-aspartate receptors determined by site-directed mutagenesis and molecular modeling | journal = Molecular Pharmacology | volume = 67 | issue = 5 | pages = 1470–84 | date = May 2005 | pmid = 15703381 | doi = 10.1124/mol.104.008185 | url = http://molpharm.aspetjournals.org/cgi/content/full/67/5/1470 }} 12. ^{{cite book | vauthors = Evans J | title = Commercial Amino Acids | pages = 101–103 | publisher = BCC Research | year = 2014 |url= http://www.bccresearch.com/market-research/biotechnology/commercial-amino-acids-bio007k.html }} 13. ^1 Transparency Market Research. Superabsorbent polymers market - global industry analysis, size, share, growth, trends and forecase, 2014-2020. (2014). 14. ^{{cite journal | vauthors = Alford DD, Wheeler AP, Pettigrew CA | title = Biodegradation of thermally synthesized polyaspartate | journal = J Environ Polym Degr | volume = 2 | pages = 225–236 | date = 1994 }} 15. ^{{cite book | vauthors = Kelling K | title = Crop Responses to Amisorb in the North Central Region | publisher = University of Wisconsin-Madison | date = 2001 }} 16. ^Global concrete floor coatings market will be worth US$1.1 bn by 2020. Transparency Market Research (2015). 17. ^Corrosion inhibitors market analysis by product, by application, by end-use industry, and segment forecasts to 2020. Grand View Research (2014) 18. ^{{cite book | first1 = D. K. | last1 = Salunkhe | first2 = S.S. | last2 = Kadam | name-list-format = vanc | title = Handbook of Fruit Science and Technology: Production, Composition, Storage, and Processing | url = https://books.google.com/books?id=v2WnS_2ZmDwC&pg=PA368 | date = 18 August 1995 | publisher = CRC Press | isbn = 978-0-8247-9643-3 | pages = 368– }} 19. ^{{cite book | first = Douglas M. | last = Considine | name-list-format = vanc | title = Foods and Food Production Encyclopedia | url = https://books.google.com/books?id=xZXuBwAAQBAJ&pg=PA114 | date = 6 December 2012 | publisher = Springer Science & Business Media | isbn = 978-1-4684-8511-0 | pages = 114– }} External links
7 : Proteinogenic amino acids|Glucogenic amino acids|Acidic amino acids|Dicarboxylic acids|Neurotransmitters|Urea cycle|NMDA receptor agonists |
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