1-(Chloro-1-pyrrolidinylmethylene)pyrrolidinium Hexafluorophosphate is a coupling reagent of the chloroformamidinium salt type, widely recognised in peptide chemistry. Its role in the laboratory is to activate carboxylic acid groups so that they can react with amines to form amide bonds — the core step in assembling a peptide chain. The reagent converts a relatively unreactive carboxylic acid into a highly reactive intermediate species, allowing the amidation reaction to proceed at mild temperatures and in a far shorter time than conventional methods require.
The properties that make this reagent a preferred choice are its high activation efficiency combined with a low tendency toward racemisation — two factors that are decisive for the success of peptide synthesis whenever a stereogenic centre must be preserved. The two pyrrolidine rings flanking the central carbon give the molecule a distinctive electronic and steric character, different from that of other uronium or phosphonium reagents. For this reason it is frequently selected when a coupling is difficult to achieve, for example with amino acids bearing bulky side chains or with sterically hindered amines. The hexafluorophosphate anion contributes to the handling character of the salt.
In Indonesian laboratories, this reagent is typically found in research groups and institutional facilities engaged in peptide synthesis, medicinal chemistry, and chemical biology, whether in universities, government research institutes, or industrial R&D units. It is normally used at bench scale for the stepwise construction of peptide sequences and for amide bond formation in general synthetic work, in settings where reaction efficiency and stereochemical integrity are both required outcomes.
- Solid-phase peptide synthesis — the reagent activates the incoming protected amino acid efficiently, allowing each coupling cycle on the resin to reach completion quickly under mild conditions.
- Solution-phase peptide coupling — its rapid activation of carboxylic acids enables amide bond formation between fragments in solution without the extended reaction times associated with conventional activation methods.
- Sterically hindered couplings — the distinctive steric and electronic character imparted by the two pyrrolidine rings makes it a useful option when bulky side chains obstruct standard uronium or phosphonium reagents.
- Stereochemically sensitive amidation — the low racemisation tendency of this reagent supports reactions in which an existing stereogenic centre must be retained throughout the coupling step.
- General amide bond formation in medicinal chemistry — routine conversion of carboxylic acids to amides during analogue preparation benefits from the reagent's high activation efficiency at mild temperature.
| Brand | TCI |
|---|---|
| CAS number | 135540-11-3 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Chemical Biology > Peptide Chemistry |
| Pack sizes | available in standard laboratory pack sizes; please confirm the currently offered packaging when ordering |
| Physical form | — |
| Storage | store in a cool, dry place in a tightly closed container, protected from moisture |
- Product code: C1379
Store the reagent in a cool, dry location inside a tightly closed original container, kept away from moisture, direct sunlight, and sources of heat or ignition. Keep the container sealed when not in use, as coupling reagents of this class are generally sensitive to atmospheric humidity. Weigh and transfer the material in a fume hood, wearing safety glasses, chemical-resistant gloves, and a laboratory coat. Avoid inhalation of dust and contact with skin or eyes. Do not store together with strong bases, strong oxidising agents, or amines. Always consult the manufacturer's Safety Data Sheet before use, and dispose of residues and contaminated materials in accordance with applicable chemical waste procedures.
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