900555

(N-Isocyanoimino)triphenylphosphorane

95%

• Synonym(e): Pinc
• Empirische Formel (Hill-System): C₁₉H₁₅N₂P
• CAS-Nummer: 73789-56-7
• Molekulargewicht: 302.31
• MDL-Nummer: MFCD09038528
• UNSPSC-Code: 12352209
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 100
• Assay: 95%
• Form: solid
• Anwendung(en): peptide synthesis
• SMILES String: [P](=N[N+]#[C-])(c3ccccc3)(c2ccccc2)c1ccccc1
• InChI: 1S/C19H15N2P/c1-20-21-22(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19/h2-16H
• InChIKey: NIDTXBFHPXMXTR-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

(N-Isocyanoimino)triphenylphosphorane (Pinc) is a bench-stable solid reagent widely used in organic synthesis. It is an amphoteric compound with unique properties that make it a versatile tool for various applications, including heterocycle synthesis and macrocyclization of peptides. Pinc facilitates cyclization and incorporation of a conformational control element into peptide macrocycles, leading to desired drug properties such as improved membrane permeability, lipophilicity, and aqueous solubility.[1] Its ability to form oxadiazoles offers opportunities for the development of new transformations.

Anwendung

As reported by the lab of Andrei Yudin, Pinc enables zwitterionic-controlled generation of peptide macrocyles from linear peptides and aldehydes. It enables the formation of disubstituted 1,3,4-oxadiazoles by intercepting the key mixed anhydride characteristic of the Ugi reaction.[2] Furthermore, the resulting peptide macrocycles containing oxadiazole exhibit improved drug properties such as cell-permeability and a rigid conformation.[3]

Leistungsmerkmale und Vorteile

• Bench-stable solid: Pinc is a stable reagent that can be easily handled and stored.
• Facilitates cyclization and incorporation of conformational control element: Pinc enables the formation of peptide macrocycles with a desired conformation, leading to improved drug properties.
• Amphoteric properties: Pinc′s amphoteric nature allows for the design of new multicomponent reactions, expanding its synthetic capabilities.
• Desired drug properties: The resulting peptide macrocycles exhibit enhanced membrane permeability, lipophilicity, and aqueous solubility, making them desirable for drug development.
• Versatile transformations: Pinc′s ability to form oxadiazoles opens up opportunities for the development of novel synthetic transformations.

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315,H319,H335
• P-Sätze: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable