324753-14-2

Usage

Uses

Used in Pharmaceutical Industry:
(MercaptoMethyl)diphenylphosphine Oxide is used as a synthetic intermediate for the production of peptide thioesters. These peptide thioesters are valuable in the development of pharmaceuticals, particularly in the synthesis of peptide-based drugs and the study of protein structure and function.
Used in Chemical Research:
Due to its unique chemical structure, (MercaptoMethyl)diphenylphosphine Oxide serves as a useful compound in chemical research. It can be employed in the investigation of new synthetic pathways, the development of novel chemical reactions, and the exploration of its reactivity with various other compounds.
Used in Material Science:
(MercaptoMethyl)diphenylphosphine Oxide's properties may also find applications in material science. Its potential use in the development of new materials with specific properties, such as improved stability or reactivity, can be explored, contributing to advancements in various industries.

Upstream product

• 1806-49-1 diphenyl(chloromethyl)phosphine oxide 
• 507-09-5 tiolacetic acid 
• 10387-40-3 potassium thioacetate 
• 1079-66-9 chloro-diphenylphosphine 
• 884-74-2 (diphenylphosphinoyl)methanol 
• 4559-70-0 Diphenylphosphine oxide 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 80738-04-1 2-(Diphenyl-phosphinoylmethylsulfanyl)-1-phenyl-ethanone 
• 324753-11-9 thioacetic acid S-[(diphenylphosphanyl)methyl] ester 
• 51649-25-3 diphenyl(α-sulfanylmethyl)phosphine oxide 
• 613688-05-4 diphenylphosphaneylmethanethiol borane complex 
• 100946-77-8 6-<1-<oxy>ethyl>-3,5-dimethyl-2-(diphenylphosphinyl)-2H-thiopyran 
• 324753-13-1 (S)-S-((diphenylphosphino)methyl) 2-acetamido-3-phenylpropanethioate 
• 324753-12-0 (acetylamino)thioacetic acid S-[(diphenylphosphanyl)methyl] ester 
• 324753-16-4 (diphenylphosphanyl)methanethiol 
• 905992-17-8 AcAlaSCH₂PPh₂ 

Relevant academic research and scientific papers

Reduction of Tertiary Phosphine Oxides by BH 3 Assisted by Neighboring Activating Groups

Tertiary sulfanylphosphine and aminoalkylphosphine oxides can be easily converted into the corresponding tertiary sulfanylphosphine- and aminoalkylphosphine-boranes, respectively, through the facile P=O bond reduction by borane complexes. The easy reduction of the strong P=O bond by BH 3, a mild reducing agent, has been achieved through an intramolecular P=O - B complexation directed by proximal SH or NH activating groups located at the α- or β-position to the P=O bond. A generalized reduction mechanism has been proposed.

A Versatile Approach for Site-Specific Lysine Acylation in Proteins

Using amber suppression in coordination with a mutant pyrrolysyl-tRNA synthetase-tRNAPylpair, azidonorleucine is genetically encoded in E. coli. Its genetic incorporation followed by traceless Staudinger ligation with a phosphinothioester allows the convenient synthesis of a protein with a site-specifically installed lysine acylation. By simply changing the phosphinothioester identity, any lysine acylation type could be introduced. Using this approach, we demonstrated that both lysine acetylation and lysine succinylation can be installed selectively in ubiquitin and synthesized histone H3 with succinylation at its K4 position (H3K4su). Using an H3K4su-H4 tetramer as a substrate, we further confirmed that Sirt5 is an active histone desuccinylase. Lysine succinylation is a recently identified post-translational modification. The reported technique makes it possible to explicate regulatory functions of this modification in proteins.

A Photo-Triggered Traceless Staudinger–Bertozzi Ligation Reaction

The use of light to control the course of a chemical/biochemical reaction is an attractive idea because of its ease of administration with high precision and fine spatial resolution. Staudinger ligation is one of the commonly adopted conjugation processes that involve a spontaneous reaction between azides and arylphosphines to form iminophosphoranes, which further hydrolyze to give stable amides. We designed an anthracenylmethyl diphenylphosphinothioester (1) that showed promising Staudinger ligation reactivity upon photo-excitation. Broadband photolysis at 360–400 nm in aqueous organic solvents induced heterolytic cleavage of its anthracenylmethyl–phosphorus bond, releasing a diphenylphosphinothioester (2) as an efficient traceless Staudinger–Bertozzi ligation reagent. The quantum yield of such a photo-induced heterolytic bond-cleavage at the optimal wavelength of photolysis (376 nm) at room temperature is ≥0.07. This work demonstrated the feasibility of photocaging arylphosphines to realize the photo-triggering of the Staudinger ligation reaction.

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

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

Thioaldehyde Diels-Alder Reactions

Thioaldehydes containing virtually any α-substitutent can be generated by photofragmentation of phenacyl sulfides.Donor-substituted derivatives are reactive toward electron-rich dienes and give 2 + 4 cycloadducts with regiochemistry corresponding to advan