imported>David E. Volk |
imported>David E. Volk |
| Line 1: |
Line 1: |
| <noinclude>{{subpages}}</noinclude>
| |
|
| |
| {{Chem infobox
| |
| |align=right
| |
| |image=[[Image:Carbodiimide.png|center|thumb|250px]]
| |
| |width=250px
| |
| |molname=carbodiimide
| |
| |synonyms=
| |
| |molformula= R1-N=C=N-R2
| |
| |molmass=
| |
| |uses=dehydration reagent
| |
| |properties=activates carboxylates
| |
| |hazards=
| |
| |iupac=
| |
| |casnumber=
| |
| }}
| |
|
| |
|
| |
| '''Carbodiimides''' are a type of dehydrating chemical most often used to activate [[carboxylic acid]]s for subsequent coupling with primary [[amine]]s, producing an [[amide]] compound. the carboxyl group is often converted to an activated compound by forming an [[N-hydroxysuccinamide]] [[ester]] or other esters.
| |
|
| |
| {{Image|Carbodiimide generic reaction.png|left|500px|Coupling of an amide group to a carboxylic acid activated by a carbodiimide.}}
| |
|
| |
| A variety of carbodiimides are commonly used, including EDAC, DIC and DCC, illustrated below. EDAC is particularly useful in aqueous reactions and is sold in a variety of biochemical reagent kits designed for coupling proteins to amines, including amines on the surface of [[quantum dot]]s or [[nanocrystal]].
| |
|
| |
| == EDAC == | | == EDAC == |
| {{Image|EDAC.png|left|250px|EDAC chemical structure.}} | | {{Image|EDAC.png|left|250px|EDAC chemical structure.}} |
|
| |
|
| The reagent [[1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide]], abbreviated as EDAC, EDC or EDCI, is a widely used reagent for coupling water soluble carboxylic acids with water soluble primary amides under aqueous conditions and within a [[pH]] range of 4-6. | | The reagent [[1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide]], abbreviated as EDAC, EDC or EDCI, is a widely used reagent for coupling water soluble carboxylic acids with water soluble primary amides under aqueous conditions and within a [[pH]] range of 4-6. |
|
| |
| == DCC ==
| |
| The reagent [[N,N'-dicyclohexylcarbodiimide]], also called 1,3-dicyclohexylcarbodiimide and abbeviated as DCC, was one of the first carbodiimides developed for amide and ester formation from carboxylic acids. It is useful for solid-phase reactions, and has been particularly useful for [[peptide]] synthesis because of its high yields for amide forming reactions and its inexpensive cost. Purification difficulties occur using this reagent, and because of this, EDC is often used preferantially to DCC.
| |
|
| |
|
| |
| {{Image|Dicyclohexylcarbodiimide.png|left|250px|N,N'-dicyclohexylcarbodiimide.}}
| |
