900555

(N-Isocyanoimino)triphenylphosphorane

95%

• Synonim(y): Pinc
• Wzór empiryczny (zapis Hilla): C₁₉H₁₅N₂P
• Numer CAS: 73789-56-7
• Masa cząsteczkowa: 302.31
• Numer MDL: MFCD09038528
• Kod UNSPSC: 12352209
• NACRES: NA.22

Właściwości

• Poziom jakości: 100
• Próba: 95%
• Formularz: solid
• Zastosowanie: peptide synthesis
• ciąg SMILES: [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
• Klucz InChI: NIDTXBFHPXMXTR-UHFFFAOYSA-N

Opis

Opis ogólny

(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.

Zastosowanie

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]

Cechy i korzyści

• 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.

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Informacja o środkach bezpieczeństwa

• Piktogramy: GHS07
• Hasło ostrzegawcze: Warning
• Zwroty wskazujące rodzaj zagrożenia: H315,H319,H335
• Zwroty wskazujące środki ostrożności: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Klasyfikacja zagrożeń: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Organy docelowe: Respiratory system
• Kod klasy składowania: 11 - Combustible Solids
• Klasa zagrożenia wodnego (WGK): WGK 3
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable