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900555 Sigma-Aldrich

(N-Isocyanoimino)triphenylphosphorane

95%

Synonym: Pinc

  • CAS Number 73789-56-7

  • Empirical Formula (Hill Notation) C19H16N2P

  • Molecular Weight 303.32

  •  MDL number MFCD09038528

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Properties

Related Categories Chemical Biology, Chemical Synthesis, Other Peptide Coupling, Peptide Coupling, Peptide Synthesis and Peptide Chemistry More...
Quality Level   100
assay   95%
form   solid
application(s)   peptide synthesis: suitable
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
InChI key   NIDTXBFHPXMXTR-UHFFFAOYSA-N

Description

Application

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).

Packaging

5 g in glass bottle

500 mg in glass insert

Other Notes

Oxadiazole grafts in peptide macrocycles
C&EN Highlight: Cyclic peptides with heterocycles are cell membrane-permeable
Technology Spotlight: Heterocycle and Cyclic Peptide Formation with Pinc

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Andrei Yudin Group - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Andrei Yudin Group - Professor Product Portal
Keywords: Building blocks, Condensations, Peptidomimetics

Heterocycle and Cyclic Peptide Formation with Pinc

Isocyanides are widely used reagents in organic synthesis, with applications ranging from materials science to drug discovery. In the course of a chemical transformation, the terminal carbon of an is...
Keywords: Cyclizations, Drug discovery, Materials Science, Organic synthesis, Ugi Reaction, transformation

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