Have you encountered bottlenecks in peptide synthesis despite optimal reaction conditions? When yields remain stubbornly low, N,N'-diisopropylcarbodiimide (DIC) might be the solution you need.
Commonly abbreviated as DIPC, this crucial organic synthesis reagent serves as a powerful coupling agent in peptide chain formation. Functioning like a molecular catalyst, DIC efficiently connects amino acids to construct complex peptide structures. High-purity DIC (98.0% by GC analysis) ensures reliable and reproducible experimental results.
Key identifiers for this compound include:
- Linear formula: (CH3)2CHN=C=NCH(CH3)2
- CAS Number: 693-13-0
- Molecular weight: 126.20 g/mol
- Beilstein Registry Number: 878281
- EC Number: 211-743-7
- PubChem Substance ID: 329755678
DIC operates through a two-stage activation mechanism:
- Carboxyl activation: Reacts with carboxylic groups to form O-acylisourea intermediates, increasing electrophilicity
- Amine attack: Nucleophilic acyl substitution forms peptide bonds while generating diisopropylurea (DIU) as byproduct
Compared to alternative coupling reagents, DIC offers distinct benefits:
- Rapid reaction kinetics
- Broad compatibility with various amino acids
- Convenient liquid handling properties
Important precautions include:
- Potential side reactions (racemization/isomerization) mitigated by additives like HOBt
- Requires proper personal protective equipment due to irritant properties
- Moisture-sensitive storage requirements
While DIC remains widely used, several alternatives exist:
- DCC (N,N'-dicyclohexylcarbodiimide) - slower reaction rates
- EDC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) - water-soluble variant
- HATU - premium-performance reagent with faster kinetics
Reagent selection should consider specific reaction parameters and desired outcomes.
