| Revision as of 16:38, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472696649 of page 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 14:12, 3 October 2024 edit Alchemization (talk | contribs)5 edits Added half sentence on how EDC is prepared with TsCl and TEA (with hyperlinks)Tag: Visual edit |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 427205038 |
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| verifiedrevid = 477207658 |
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| IUPACName = 3-(ethyliminomethyleneamino)-N,N-dimethyl-propan-1-amine |
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| PIN = 3-{amino}-''N'',''N''-dimethylpropan-1-amine |
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| ImageFile = EDC Structure.png |
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| ImageFile = EDC Structure.png |
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| ImageSize = 210 |
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| ImageAlt = Skeletal formula of EDC |
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| ImageFile1 = EDC molecule ball.png |
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| ImageSize1 = 240 |
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| ImageAlt1 = Ball-and-stick model of the EDC molecule |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| InChIKey = LMDZBCPBFSXMTL-UHFFFAOYAH |
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| InChIKey = LMDZBCPBFSXMTL-UHFFFAOYAH |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C8H17N3/c1-4-9-8-10-6-5-7-11(2)3/h4-7H2,1-3H3 |
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| StdInChI = 1S/C8H17N3/c1-4-9-8-10-6-5-7-11(2)3/h4-7H2,1-3H3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 1892-57-5 |
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| CASNo = 1892-57-5 |
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| PubChem = 15908 |
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| CASNo1 = 25952-53-8 |
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| CASNo1_Comment = (hydrochloride) |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = RJ5OZG6I4A |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = 19W5TL0WJ4 |
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| UNII1_Comment = (hydrochloride) |
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| PubChem = 15908 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 15119 |
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| ChemSpiderID = 15119 |
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| SMILES = N(=C=N\CCCN(C)C)\CC |
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| SMILES = CCN=C=NCCCN(C)C |
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| InChI = 1/C8H17N3/c1-4-9-8-10-6-5-7-11(2)3/h4-7H2,1-3H3 |
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| InChI = 1/C8H17N3/c1-4-9-8-10-6-5-7-11(2)3/h4-7H2,1-3H3 |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=8 | H = 17 | N = 3 }} |
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| C=8 | H = 17 | N = 3}} |
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| Section7 = {{Chembox Hazards |
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| Section7 = {{Chembox Hazards |
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| ExternalSDS = }} |
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'''1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide''' ('''EDC''', '''EDAC''' or '''EDCI''') is a water-soluble ] usually handled as the ].<ref>{{cite journal|title=1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide Hydrochloride|journal=E-EROS Encyclopedia of Reagents for Organic Synthesis|year=2001|author=Richard S. Pottorf, Peter Szeto|doi=10.1002/047084289X.re062}}</ref> |
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It is typically employed in the 4.0-6.0 ] range. It is generally used as a carboxyl activating agent for the coupling of primary amines to yield amide bonds. While other carbodiimides like ] (DCC) or ] (DIC) are also employed for this purpose, EDC has the advantage that the urea byproduct formed (often challenging to remove in the case of DCC or DIC) can be washed away from the amide product using dilute acid. Additionally, EDC can also be used to activate ] groups in order to form phosphomonoesters and phosphodiesters. Common uses for this carbodiimide include ], ] to ]s, but also in the preparation of ]s. EDC is often used in combination with ] (NHS) for the immobilisation of large ]. Recent work has also used EDC to ] of uracil nucleobases in RNA.<ref name="EDC1">{{cite journal |last1=Mitchell |first1=D |last2=Renda |first2=A |last3=Douds |first3=C |last4=Babitzke |first4=P |last5=Assmann |first5=S |last6=Bevilacqua |first6=P |title=In vivo RNA structural probing of uracil and guanine base-pairing by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) |journal=RNA |date=2019 |volume=25 |issue=1 |pages=147–157 |doi=10.1261/rna.067868.118|doi-access=free |pmid=30341176 |pmc=6298566}}</ref><ref name="EDC2">{{cite journal |last1=Wang |first1=PY |last2=Sexton |first2=AN |last3=Culligan |first3=WJ |last4=Simon |first4=MD |title=Carbodiimide reagents for the chemical probing of RNA structure in cells |journal=RNA |date=2019 |volume=25 |issue=1 |pages=135–146 |doi=10.1261/rna.067561.118|doi-access=free |pmid=30389828 |pmc=6298570}}</ref> |
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==Preparation== |
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EDC is commercially available. It may be prepared by coupling ethyl isocyanate to ''N'',''N''-dimethylpropane-1,3-diamine to give a ], followed by a ] mediated by ] and ]:<ref>{{cite journal | doi = 10.1021/jo01351a600 | year = 1961 |author1=Sheehan, John |author2=Cruickshank, Philip |author3=Boshart, Gregory | title =A Convenient Synthesis of Water-Soluble Carbodiimides | journal = ] | volume = 26 | pages = 2525 | issue = 7}}</ref> |
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:] |
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== Mechanism == |
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] |
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EDC couples primary amines, and other nucleophiles,<ref>{{Cite journal|url=https://pubs.rsc.org/en/content/articlelanding/2015/np/c4np00106k|doi = 10.1039/C4NP00106K|title = Ester coupling reactions – an enduring challenge in the chemical synthesis of bioactive natural products|year = 2015|last1 = Tsakos|first1 = Michail|last2 = Schaffert|first2 = Eva S.|last3 = Clement|first3 = Lise L.|last4 = Villadsen|first4 = Nikolaj L.|last5 = Poulsen|first5 = Thomas B.|journal = Natural Product Reports|volume = 32|issue = 4|pages = 605–632|pmid = 25572105}}</ref> to carboxylic acids by creating an activated ester leaving group. First, the carbonyl of the acid attacks the carbodiimide of EDC, and there is a subsequent proton transfer. The primary amine then attacks the carbonyl carbon of the acid which forms a tetrahedral intermediate before collapsing and discharging the urea byproduct. The desired amide is obtained.<ref>{{Cite web|url=https://www.thermofisher.com/us/en/home/life-science/protein-biology/protein-biology-learning-center/protein-biology-resource-library/pierce-protein-methods/carbodiimide-crosslinker-chemistry.html|title=Carbodiimide Crosslinker Chemistry - US|website=www.thermofisher.com|language=en|access-date=2019-05-10}}</ref> |
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== Safety == |
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''In vivo'' dermal sensitization studies according to ] 429<ref>{{Cite book |last=OECD |url=https://www.oecd-ilibrary.org/environment/test-no-429-skin-sensitisation_9789264071100-en |title=Test No. 429: Skin Sensitisation: Local Lymph Node Assay |date=2010 |publisher=Organisation for Economic Co-operation and Development |location=Paris |language=en}}</ref> confirmed EDC is a strong skin ], showing a response at <0.01 wt% in the ] placing it in ] (GHS) Dermal Sensitization Category 1A.<ref>{{Cite journal |last=Graham |first=Jessica C. |last2=Trejo-Martin |first2=Alejandra |last3=Chilton |first3=Martyn L. |last4=Kostal |first4=Jakub |last5=Bercu |first5=Joel |last6=Beutner |first6=Gregory L. |last7=Bruen |first7=Uma S. |last8=Dolan |first8=David G. |last9=Gomez |first9=Stephen |last10=Hillegass |first10=Jedd |last11=Nicolette |first11=John |last12=Schmitz |first12=Matthew |date=2022-06-20 |title=An Evaluation of the Occupational Health Hazards of Peptide Couplers |url=https://pubs.acs.org/doi/10.1021/acs.chemrestox.2c00031 |journal=Chemical Research in Toxicology |language=en |volume=35 |issue=6 |pages=1011–1022 |doi=10.1021/acs.chemrestox.2c00031 |issn=0893-228X |pmc=9214767 |pmid=35532537}}</ref> Thermal hazard analysis by ] shows EDC poses minimal explosion risks.<ref>{{Cite journal |last=Sperry |first=Jeffrey B. |last2=Minteer |first2=Christopher J. |last3=Tao |first3=JingYa |last4=Johnson |first4=Rebecca |last5=Duzguner |first5=Remzi |last6=Hawksworth |first6=Michael |last7=Oke |first7=Samantha |last8=Richardson |first8=Paul F. |last9=Barnhart |first9=Richard |last10=Bill |first10=David R. |last11=Giusto |first11=Robert A. |last12=Weaver |first12=John D. |date=2018-09-21 |title=Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing |url=https://pubs.acs.org/doi/10.1021/acs.oprd.8b00193 |journal=Organic Process Research & Development |language=en |volume=22 |issue=9 |pages=1262–1275 |doi=10.1021/acs.oprd.8b00193 |issn=1083-6160}}</ref> |
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==References== |
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<references/> |
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==Further reading== |
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* {{Cite journal |author1=López-Alonso, JP |author2=Diez-Garcia, F |author3=Font, J |author4=Ribó, M |author5=Vilanova, M |author6=Scholtz, JM |author7=González, C |author8=Vottariello, F |author9=Gotte, G |author10=Libonati, M |author11=Laurents, DV | journal = Bioconjugate Chemistry | year = 2009 | doi = 10.1021/bc9001486 | title = Carbodiimide EDC Induces Cross-Links That Stabilize RNase A C-dimer against Dissociation: EDC Adducts Can Affect Protein Net Charge, Conformation and Activity | volume = 20 | pages = 1459–1473 | issue = 8|pmid=19606852 }} |
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* {{Cite journal |author1=Nakajima, N |author2=Ikada, Y | journal = ] | year = 1995 | doi = 10.1021/bc00031a015 | title = Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media | volume = 6 |issue=1 | pages = 123–130|pmid=7711098 }} |
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{{DEFAULTSORT:Ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1-}} |
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