(ISOCYANOIMINO)TRIPHENYLPHOSPHORANE Chemical Properties

Melting point:

160-161 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

color 

White to Light yellow to Light orange

Major Application

peptide synthesis

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

SMILES

[P](=N[N+]#[C-])(c3ccccc3)(c2ccccc2)c1ccccc1

Safety Information

WGK Germany 

WGK 3

HS Code 

29319090

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

(ISOCYANOIMINO)TRIPHENYLPHOSPHORANE Usage And Synthesis

Uses

Despite growing interest for therapeutic and other biological applications, cyclic peptidomimetics are challenging to synthesize. As reported by the lab of Andrei Yudin, (N-isocyanoimino)triphenylphosphorane (Pinc
) enables zwitterionic-controlled generation of peptide macrocyles from linear peptides and aldehydes. Containing a 1,3,4-oxadiazole, the resulting peptide exhibits both improved membrane permeability, lipophilicity, and aqueous solubility.
Different functional groups can be introduced by varying the aldehyde, and initial work used propionaldehyde (538124), phenylacetaldehyde (107395), and isovaleraldehyde (146455).

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