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López-Alonso, JP; Diez-Garcia, F; Font, J; Ribó, M; Vilanova, M; Scholtz, JM; González, C; Vottariello, F; Gotte, G; Libonati, M; Laurents, DV (2009). "Carbodiimide EDC Induces Cross-Links That
Stabilize RNase A C-dimer against Dissociation: EDC Adducts Can Affect Protein Net Charge, Conformation and
536:
EDC couples primary amines, and other nucleophiles, 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
451:(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
875:
Sperry, Jeffrey B.; Minteer, Christopher J.; Tao, JingYa; Johnson, Rebecca; Duzguner, Remzi; Hawksworth, Michael; Oke, Samantha; Richardson, Paul F.; Barnhart, Richard; Bill, David R.; Giusto, Robert A.; Weaver, John D. (2018-09-21).
776:
817:
Graham, Jessica C.; Trejo-Martin, Alejandra; Chilton, Martyn L.; Kostal, Jakub; Bercu, Joel; Beutner, Gregory L.; Bruen, Uma S.; Dolan, David G.; Gomez, Stephen; Hillegass, Jedd; Nicolette, John; Schmitz, Matthew (2022-06-20).
561:
531:
The scheme above shows the general mechanistic steps for EDC-mediated coupling of carboxylic acids and amines under acidic conditions. The tetrahedral intermediate and the aminolysis steps are not shown
394:
288:
443:
range. It is generally used as a carboxyl activating agent for the coupling of primary amines to yield amide bonds. While other carbodiimides like
483:
993:
565:
253:
444:
448:
801:
609:"In vivo RNA structural probing of uracil and guanine base-pairing by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC)"
401:
188:
709:
Sheehan, John; Cruickshank, Philip; Boshart, Gregory (1961). "A Convenient
Synthesis of Water-Soluble Carbodiimides".
217:
553:
948:
Nakajima, N; Ikada, Y (1995). "Mechanism of Amide
Formation by Carbodiimide for Bioconjugation in Aqueous Media".
537:
a tetrahedral intermediate before collapsing and discharging the urea byproduct. The desired amide is obtained.
363:
151:
988:
950:
739:"Ester coupling reactions – an enduring challenge in the chemical synthesis of bioactive natural products"
113:
878:"Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing"
455:
groups in order to form phosphomonoesters and phosphodiesters. Common uses for this carbodiimide include
737:
Tsakos, Michail; Schaffert, Eva S.; Clement, Lise L.; Villadsen, Nikolaj L.; Poulsen, Thomas B. (2015).
584:
Richard S. Pottorf, Peter Szeto (2001). "1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide
Hydrochloride".
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EDC is commercially available. It may be prepared by coupling ethyl isocyanate to
177:
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Mitchell, D; Renda, A; Douds, C; Babitzke, P; Assmann, S; Bevilacqua, P (2019).
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660:"Carbodiimide reagents for the chemical probing of RNA structure in cells"
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Globally
Harmonized System of Classification and Labelling of Chemicals
164:
932:
820:"An Evaluation of the Occupational Health Hazards of Peptide Couplers"
371:
Except where otherwise noted, data are given for materials in their
564:(GHS) Dermal Sensitization Category 1A. Thermal hazard analysis by
526:
112:
102:
806:. Paris: Organisation for Economic Co-operation and Development.
557:
549:
503:
222:
440:
803:
389:
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Wang, PY; Sexton, AN; Culligan, WJ; Simon, MD (2019).
262:
InChI=1S/C8H17N3/c1-4-9-8-10-6-5-7-11(2)3/h4-7H2,1-3H3
586:
E-EROS Encyclopedia of
Reagents for Organic Synthesis
272:
InChI=1/C8H17N3/c1-4-9-8-10-6-5-7-11(2)3/h4-7H2,1-3H3
176:
87:
80:
17:1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide
414:1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide
8:
556:, showing a response at <0.01 wt% in the
882:Organic Process Research & Development
548:dermal sensitization studies according to
237:
154:
132:
15:
851:
777:"Carbodiimide Crosslinker Chemistry - US"
685:
675:
634:
624:
568:shows EDC poses minimal explosion risks.
203:
196:
471:. EDC is often used in combination with
439:It is typically employed in the 4.0-6.0
576:
566:differential scanning calorimetry (DSC)
502:-dimethylpropane-1,3-diamine to give a
293:
258:
233:
478:(NHS) for the immobilisation of large
145:
265:Key: LMDZBCPBFSXMTL-UHFFFAOYSA-N
7:
552:429 confirmed EDC is a strong skin
482:. Recent work has also used EDC to
275:Key: LMDZBCPBFSXMTL-UHFFFAOYAH
167:
14:
467:, but also in the preparation of
514:
379:
329:
323:
31:
22:
824:Chemical Research in Toxicology
375:(at 25 °C , 100 kPa).
836:10.1021/acs.chemrestox.2c00031
486:of uracil nucleobases in RNA.
317:
1:
558:Local Lymph Node Assay (LLNA)
1010:
484:assess the structure state
994:Reagents for biochemistry
369:
351:
304:
284:
249:
64:
44:
39:
30:
21:
894:10.1021/acs.oprd.8b00193
594:10.1002/047084289X.re062
445:dicyclohexylcarbodiimide
364:External MSDS (HCl Salt)
743:Natural Product Reports
449:diisopropylcarbodiimide
432:usually handled as the
58:-dimethylpropan-1-amine
951:Bioconjugate Chemistry
921:Bioconjugate Chemistry
677:10.1261/rna.067561.118
626:10.1261/rna.067868.118
533:
530:
428:) is a water-soluble
208: (hydrochloride)
92: (hydrochloride)
781:www.thermofisher.com
461:protein crosslinking
46:Preferred IUPAC name
964:10.1021/bc00031a015
724:10.1021/jo01351a600
476:-hydroxysuccinimide
347: g·mol
18:
755:10.1039/C4NP00106K
534:
402:Infobox references
16:
933:10.1021/bc9001486
457:peptide synthesis
410:Chemical compound
408:
407:
358:Safety data sheet
218:CompTox Dashboard
114:Interactive image
1001:
975:
944:
927:(8): 1459–1473.
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749:(4): 605–632.
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619:(1): 147–157.
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65:Identifiers
55:
51:
919:Activity".
718:(7): 2525.
532:explicitly.
508:dehydration
490:Preparation
305:Properties
152:100.015.982
983:Categories
786:2019-05-10
572:References
554:sensitizer
340:Molar mass
205:19W5TL0WJ4
198:RJ5OZG6I4A
125:ChemSpider
101:3D model (
89:25952-53-8
72:CAS Number
50:3-{amino}-
902:1083-6160
844:0893-228X
523:Mechanism
453:phosphate
447:(DCC) or
82:1892-57-5
941:19606852
862:35532537
763:25572105
696:30389828
645:30341176
352:Hazards
972:7711098
853:9214767
687:6298570
636:6298566
546:In vivo
395:what is
393: (
345:155.245
165:PubChem
970:
939:
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684:
643:
633:
541:Safety
390:verify
387:
360:(SDS)
289:SMILES
40:Names
254:InChI
178:15908
134:15119
103:JSmol
968:PMID
937:PMID
898:ISSN
858:PMID
840:ISSN
759:PMID
692:PMID
641:PMID
550:OECD
504:urea
426:EDCI
422:EDAC
189:UNII
960:doi
929:doi
890:doi
848:PMC
832:doi
751:doi
720:doi
682:PMC
672:doi
664:RNA
631:PMC
621:doi
613:RNA
590:doi
463:to
436:.
424:or
418:EDC
223:EPA
168:CID
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324:H
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318:C
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56:N
54:,
52:N
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