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900555

Sigma-Aldrich

(N-Isocyanoimino)triphenylphosphorane

95%

Synonyme(s) :

Pinc

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About This Item

Formule empirique (notation de Hill):
C19H15N2P
Numéro CAS:
73789-56-7
Poids moléculaire :
302.31
Numéro MDL:
MFCD09038528
Code UNSPSC :
12352209
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

95%

Forme

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

Clé InChI

NIDTXBFHPXMXTR-UHFFFAOYSA-N

Description générale

(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.

Caractéristiques et avantages

  • 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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
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)
Oxadiazole grafts in peptide macrocycles
Frost JR, Scully CCG, Yudin AK.
Nature Chemistry, 8(12), 1105-1111 (2016)

Articles

Heterocycle and Cyclic Peptide Formation with N-(isocyamino)triphenylphosphorane (Pinc)

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

Contenu apparenté

Yudin Group – Professor Product Portal

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.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

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