105832-38-0

Basic information

• Product Name: TSTU
• Synonyms: 2-SUCCINIMIDO-1,1,3,3-TETRAMETHYLURONIUM TETRAFLUOROBORATE;HONSTU;O-(N-SUCCINIMIDYL)-1,1,3,3-TETRAMETHYLURONIUM TETRAFLUOROBORATE;O-(N-SUCCINIMIDYL)-N,N,N',N'-TETRAMETHYL URONIUM BF4;O-(N-SUCCINIMIDYL)-N,N,N',N'-TETRAMETHYLURONIUM TETRAFLUOROBORATE;N,N,N',N'-TETRAMETHYL-O-(N-SUCCINIMIDYL)URONIUM TETRAFLUOROBORATE;N,N,N',N'-TETRAMETHYL-O-(SUCCINIMIDYL)URONIUM TETRAFLUOROBORATE;TSTU
• CAS NO: 105832-38-0
• Molecular Formula: BF₄*C₉H₁₆N₃O₃
• Molecular Weight: 301.05
• EINECS: -0
• Product Categories: Coupling Reagent;Peptide Coupling Reagents;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Succinimides;Peptide Synthesis;Synthetic Organic Chemistry;Peptide
• Mol File: 105832-38-0.mol

Chemical Properties

• Melting Point: 198-201 °C(lit.)
• Appearance: White to off-white/Crystalline Powder or Needles
• Density: 1.41 g/cm
• Storage Temp.: 2-8°C
• Solubility: acetonitrile: 0.1 g/mL, clear
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: TSTU(CAS DataBase Reference)
• NIST Chemistry Reference: TSTU(105832-38-0)
• EPA Substance Registry System: TSTU(105832-38-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: 1759
• WGK Germany: 3
• F: 8-10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 105832-38-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
TSTU is used as a peptide coupling reagent for the clean in-situ formation of N-succinimidyl active esters. This application is particularly important in the synthesis of peptides and other biomolecules, as it facilitates the formation of amide bonds between carboxylic acid and amine groups, leading to the creation of desired peptide structures.
Used in Chemical Synthesis:
TSTU is used as a reagent in chemical synthesis, specifically for converting carboxylates to N-succinimidyl active esters. This conversion is crucial in the formation of various chemical compounds and contributes to the development of new materials and products in the chemical industry.
Used in Research and Development:
TSTU is utilized as a peptide coupling reagent in solvent systems, which is essential for research and development in the field of biochemistry and molecular biology. This application aids in the study of protein structure, function, and interactions, as well as the development of new drugs and therapies.

Upstream product

• 56043-45-9 N,N,N',N'-tetramethylchlorformamidinium chloride 
• 67007-51-6 N-hydroxysuccinimide potassium salt 
• 632-22-4 tetramethylurea 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 125700-67-6 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 

Downstream Products

• 200554-19-4 7-amino-3-((((succinimidyl)oxy)carbonyl)methyl)-4-methylcoumarin-6-sulfonic acid 
• 114932-60-4 4-(1-pyrene)butyric acid N-hydroxysuccinimide ester 
• 532931-48-9 2-(diphenylphosphanyl)terephthalic acid 1-methyl ester 4-(N-succinimidyl) ester 
• 66134-67-6 p-fluorobenzoic acid succinimidyl ester 
• 141762-27-8 N-succinimidyl 4-[18F]fluorobenzoate 
• 946569-97-7 3-acetylbenzoic acid 2,5-dioxopyrrolidin-1-yl ester 
• 946570-04-3 3-prop-2-ynyloxy-benzoic acid 2,5-dioxopyrrolidin-1-yl ester 
• 946570-28-1 5-acetyl-2-(3-azidopropoxy)benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 146368-16-3 3H-indolium-1-(5-carboxypentyl)-2-[(1E,3E)-3-(1-ethyl-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene)-1-propenyl]-3,3-dimethyl-5-sulfo-, inner salt, succinimidyl ester 
• 917979-27-2 3H-indolium-2-[(1E,3E,5E)-5-[1-(5-carboxypentyl)-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene]-1,3-pentadienyl]-1-ethyl-3,3-dimethyl-5-sulfo-, inner salt, succinimidyl ester 
• 122030-76-6 4-acetylbenzoic acid 2,5-dioxopyrrolidin-1-yl ester 
• 905973-35-5 2,5-dioxopyrrolidine-1-yl 3-(((tert-butoxycarbonyl)aminoxy)methyl)benzoate 
• 944275-14-3 2-(2,3-dichloro-phenyl)-thiazole-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 1206209-82-6 C₁₆H₁₂N₂O₅S 

Relevant articles and documents

Highly efficient one-pot assembly of peptides by double chemoselective coupling

This study describes a methodological advancement in solution-phase peptide synthesis via the development of a convenient and operational protocol to synthesize oligopeptides in a one-pot three-step cascade method, in which two peptide bonds are introduced chemoselectively. Tri- to hexapeptides were obtained in high global yields (80-95%) with virtually no epimerization as determined via HPLC. The methodology described herein represents a faster, easier and milder approach to the synthesis of peptides, and it operates at equimolar amounts. This protocol comprises the formation of secondary and tertiary amides and is compatible with Z, Boc and Fmoc N-protecting groups as well as the use of d/l and non-proteinogenic amino acids.

NEW COUPLING REAGENTS IN PEPTIDE CHEMISTRY

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) has been applied as coupling reagent to solid phase peptide synthesis.Furthermore, a general synthetic procedure for new derivatives of different N-hydroxy compounds has been developed.They either act as excellent activating reagents causing low racemization during condensation of peptide segments or are useful tools for the formation of active esters suitable for couplings in mixed aqueous / organic media, respectively.