324753-11-9

Basic information

• Product Name: (Diphenylphosphino)Methanethiol S-Acetate
• Synonyms: (Diphenylphosphino)Methanethiol S-Acetate;(Diphenylphosphino)Methanyl Thiolacetate (Diphenylphosphino)Methanethiol precursor);1-(Diphenylphosphino)Methanethiol S-Acetate;Ethanethioic Acid S-[(Diphenylphosphino)Methyl] Ester
• CAS NO: 324753-11-9
• Molecular Formula: C₁₅H₁₅OPS
• Molecular Weight: 289
• Product Categories: Aromatics;Phosphorylating and Phosphitylating Agents;Sulfur & Selenium Compounds;Intermediates;Aromatics, Phosphorylating and Phosphitylating Agents, Sulfur & Selenium Compounds
• Mol File: 324753-11-9.mol

Chemical Properties

• Boiling Point: 369.6±25.0 °C(Predicted)
• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: (Diphenylphosphino)Methanethiol S-Acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (Diphenylphosphino)Methanethiol S-Acetate(324753-11-9)
• EPA Substance Registry System: (Diphenylphosphino)Methanethiol S-Acetate(324753-11-9)

Safety Data

• Hazardous Substances Data: 324753-11-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(Diphenylphosphino)Methanethiol S-Acetate is used as a precursor for the production of peptide thioesters, which are important in the synthesis of biologically active peptides and peptidomimetics. These peptide thioesters play a crucial role in various drug discovery and development processes, contributing to the advancement of novel therapeutic agents.
Used in Chemical Synthesis:
(Diphenylphosphino)Methanethiol S-Acetate is used as a stable precursor to the unstable (Diphenylphosphino)methanethiol. The detailed procedure for the preparation of the thiol from the thiolacetate, along with spectral data, can be provided upon request. This allows researchers and chemists to access the desired thiol compound in a controlled and efficient manner, facilitating further chemical reactions and applications.

Upstream product

• 324753-14-2 S-(diphenylphosphinoyl)methyl ethanethioate 
• 1806-49-1 diphenyl(chloromethyl)phosphine oxide 
• 446822-71-5 (borane)diphenylphosphinomethanethiol acetate 
• 67-56-1 methanol 
• 76-05-1 trifluoroacetic acid 
• 1079-66-9 chloro-diphenylphosphine 
• 884-74-2 (diphenylphosphinoyl)methanol 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 69753-67-9 N-acetyl-N'-benzylglycineamide 
• 324753-16-4 (diphenylphosphanyl)methanethiol 
• 905992-17-8 AcAlaSCH₂PPh₂ 
• 324753-12-0 (acetylamino)thioacetic acid S-[(diphenylphosphanyl)methyl] ester 
• 324753-13-1 (S)-S-((diphenylphosphino)methyl) 2-acetamido-3-phenylpropanethioate 
• 588-46-5 N-(phenylmethyl)acetamide 
• 543-24-8 N-acetylglycine 
• 1440529-30-5 C₂₂H₃₇NO₈ 
• 1440529-31-6 C₂₀H₃₅NO₇ 

Relevant articles and documents

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.

Traceless Staudinger acetylation of azides in aqueous buffers

In this paper, we demonstrate the applicability of water-soluble p-dimethylaminoethyl substituted phosphinomethanethiol in acetyl transfer reactions by the traceless Staudinger ligation with unprotected *-azido lysine containing peptides in aqueous buffer systems. Additionally, we present an improved synthesis pathway for the water-soluble phosphinothiol linkers requiring less steps in a comparable overall yield in comparison to previously published protocols.

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.

Catalyst-free alcoholysis of phosphane-boranes: a smooth, cheap, and efficient deprotection procedure

Catalyst-free alcoholytic deprotection of borane-protected phosphorus compounds offers a smooth, efficient, and clean alternative to existing deprotection methods. In this paper we report our results on the general applicability of deprotecting phosphane-

Chemoselective peptide cyclization by traceless staudinger ligation

(Chemical Equation Presented) Two birds with one stone! An intramolecular traceless Staudinger ligation was employed to synthesize cyclic peptides. The final amide bond formation was induced by deprotection of the azidopeptide phosphinothioesters. Treatment with trifluoroacetic acid (TFA) results in the simultaneous removal of the borane along with the protecting groups on the peptide side chains, and chemoselective amide bond cyclization ensues.

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.