324753-16-4

Usage

Uses

Used in Pharmaceutical Industry:
(Diphenylphosphino)methanethiol is used as a reagent for the production of peptide thioesters. It plays a crucial role in the synthesis of peptide-based drugs, which have potential applications in treating various diseases and disorders.
Used in Chemical Synthesis:
(Diphenylphosphino)methanethiol is used as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure allows for the formation of new chemical bonds and the creation of novel molecules with desired properties.
Used in Material Science:
(Diphenylphosphino)methanethiol can be used as a component in the development of new materials with specific properties, such as improved stability, reactivity, or selectivity. Its incorporation into materials can lead to advancements in areas like catalysis, sensors, and coatings.

InChI:InChI=1/C13H13PS/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2

Upstream product

• 324753-11-9 thioacetic acid S-[(diphenylphosphanyl)methyl] ester 
• 613688-05-4 diphenylphosphaneylmethanethiol borane complex 
• 324753-14-2 S-(diphenylphosphinoyl)methyl ethanethioate 
• 1806-49-1 diphenyl(chloromethyl)phosphine oxide 

Downstream Products

• 905992-17-8 AcAlaSCH₂PPh₂ 
• 51649-25-3 diphenyl(α-sulfanylmethyl)phosphine oxide 
• 1137522-93-0 6-benzyl-S-[(diphenylphosphanyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carbothioate 
• 1337909-89-3 C₃₀H₃₇N₆O₇PS 
• 324753-12-0 (acetylamino)thioacetic acid S-[(diphenylphosphanyl)methyl] ester 

Relevant academic research and scientific papers

Use of 2-[18F]fluoroethylazide for the Staudinger ligation - Preparation and characterisation of GABAA receptor binding 4-quinolones

The labelling reagent 2-[18F]fluoroethylazide was used in a traceless Staudinger ligation. This reaction was employed to obtain the GABAA receptor binding 6-benzyl-4-oxo-1,4-dihydro-quinoline-3- carboxylic acid (2-[18F]flu

Acidic and basic deprotection strategies of borane-protected phosphinothioesters for the traceless Staudinger ligation

The traceless Staudinger ligation has recently found various applications in the field of peptide synthesis and modification, including immobilization and cyclization strategies. In this report, we utilize the traceless Staudinger ligation in the formation of amide bonds, which allows the acquisition of acylated aminosugars and peptides as well as the cyclization of peptides. A key element in these synthetic procedures is the use of a borane-protected phosphinomethanethiol, which is demonstrated to be prone towards oxidation in its unprotected form, during the synthesis of phosphinothioesters. In combination with acidic and basic deprotection strategies for the borane-protected phosphinothioesters, amide bonds can be formed in the presence of azides in moderate to good overall yields.

Targeting of polyamidoamine-DNA nanoparticles using the Staudinger ligation: Attachment of an RGD motif either before or after complexation

Two new methods for the modular synthesis of targeted gene delivery systems are reported. The PEGylated polyamidoamine DMEDA-PEG-DMEDA-(MBA-DMEDA)n+1-PEG-DMEDA 3 was sequentially modified to contain an integrin-binding peptide ligand via the Staudinger ligation. The conjugation of the ligand was achieved either before particle complexation (precomplexation) or after particle complexation (postcomplexation). Comparison of the two systems showed that postcomplexation strategy led to small and discrete toroidal nanoparticles whilst the precomplexation particles showed loose complexes. The targeted particles showed an increased uptake into cells compared to unmodified complexes however no significant increase in transfection was seen.

Staudinger ligation of peptides at non-glycyl residues

The Staudinger ligation provides a means to form an amide bond between a phosphinothioester and azide. This reaction holds promise for the ligation of peptides en route to the total chemical synthesis of proteins. (Diphenylphosphino)methanethiol is the mo

CHEMICAL SYNTHESIS OF REAGENTS FOR PEPTIDE COUPLING

The present invention provides improved methods for synthesis of phosphinothiol reagents, as well as novel protected reagents, for use in formation of amide bonds, and particularly for peptide ligation. The invention provides phosphineborane complexes useful as reagents in the formation of amide bonds, particularly for the formation of an amide bond between any two of an amino acid, a peptide, or a protein.

Staudinger ligation of α-azido acids retains stereochemistry

The Staudinger ligation of peptides with a C-terminal phosphinothioester and N-terminal azide is an emerging method in protein chemistry. Here, the first Staudinger ligations of nonglycyl azides are reported and shown to proceed both in nearly quantitative yield and with no detectable effect on the stereochemistry at the α-carbon of the azide. These results demonstrate further the potential of the Staudinger ligation as a general method for the total synthesis of proteins from peptide fragments.

High-yielding staudinger ligation of a phosphinothioester and azide to form a peptide

(eqution presented) The Staudinger ligation can be used to couple a peptide with a C-terminal phosphinothioester to another with an N-terminal α-azido group to form a single peptide that contains no residual atoms. Here, diphenylphosphinomethanethiol thio