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Merck

900555

Sigma-Aldrich

(N-Isocyanoimino)triphenylphosphorane

95%

Sinónimos:

Pinc

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About This Item

Fórmula empírica (notación de Hill):
C19H15N2P
Número de CAS:
Peso molecular:
302.31
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22

Quality Level

assay

95%

form

solid

application(s)

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

InChI key

NIDTXBFHPXMXTR-UHFFFAOYSA-N

General description

(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. Its ability to form oxadiazoles offers opportunities for the development of new transformations.

Application

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. Furthermore, the resulting peptide macrocycles containing oxadiazole exhibit improved drug properties such as cell-permeability and a rigid conformation.

Features and Benefits

  • 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.

pictograms

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signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Visite la Librería de documentos

Cyclic peptides with heterocycles are cell membrane-permeable : Oxadiazole-containing peptidomimetic macrocycles have potential as drugs
Stu Borman
Chemical and Engineering News, 94(43) (2016)
N-Isocyanoiminotriphenylphosphorane: Synthesis, Coordination Chemistry, and Reactions at the Metal
Weinberger B, Fehlhammer WP.
Angewandte Chemie (International Edition in English), 19(6), 480-481 (1980)
Novel One-Pot, Four-Component Condensation Reaction: An Efficient Approach for the Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazole Derivatives by a Ugi-4CR/aza-Wittig Sequence
Ramazani A, Rezaei A.
Organic Letters, 12(12), 2852-2855 (2010)
Oxadiazole grafts in peptide macrocycles
Frost JR, Scully CCG, Yudin AK.
Nature Chemistry, 8(12), 1105-1111 (2016)

Artículos

Isocyanides are widely used reagents in organic synthesis, with applications ranging from materials science to drug discovery.

Contenido relacionado

The Yudin laboratory is known for the development of amphoteric molecules and their application in synthesis. The corresponding reagents possess nucleophilic and electrophilic functional groups that do not prematurely react with each other.

Nuestro equipo de científicos tiene experiencia en todas las áreas de investigación: Ciencias de la vida, Ciencia de los materiales, Síntesis química, Cromatografía, Analítica y muchas otras.

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