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(N-Isocyanoimino)triphenylphosphorane

Name: (<I>N</I>-Isocyanoimino)triphenylphosphorane
Brand: ALDRICH

95%

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Synonym(s):

Pinc

Empirical Formula (Hill Notation):

C₁₉H₁₅N₂P

CAS Number:

73789-56-7

Molecular Weight:

302.31

MDL number:

MFCD09038528

Quality Level

100

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

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

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

GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Precautionary Statements

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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)

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)

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)

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.