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
• Article Data: 2

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

Chemical Properties

White crystalline

Uses

Different sources of media describe the Uses of 105832-38-0 differently. You can refer to the following data:
1. peptide coupling reagent converts carboxylates to N-succinimidyl active esters
2. Reagent for the clean in-situ formation of N-succinimidyl active esters
3. TSTU is used as a peptide coupling reagent in solvent systems.

General Description

N,N,N′,N′-Tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate is commonly used for the conversion of carboxylic acid into the corresponding N-hydroxysuccinimidyl (NHS) ester.

Upstream product

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

Downstream Products

• 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 
• 104211-94-1 lithocholic acid succinimidyl ester 
• 104400-52-4 2-(4-isobutylphenyl)propionic acid N-oxysuccinimide ester 
• 104425-42-5 [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2,5-dioxopyrrolidin-1-yl ester 
• 947698-90-0 4-{3-[1,2-dihydro-6,7-dimethoxy-3-(4-methoxyphenyl)-2-oxoquinolin-1-yl]propyl}benzeneacetic acid 2,5-dioxopyrrolyn-1-yl ester 
• 1429036-21-4 C₁₇H₁₆N₄O₇S₂ 
• 141762-27-8 N-succinimidyl 4-[18F]fluorobenzoate 
• 66134-67-6 p-fluorobenzoic acid succinimidyl ester 
• 532931-48-9 2-(diphenylphosphanyl)terephthalic acid 1-methyl ester 4-(N-succinimidyl) ester 
• 114932-60-4 4-(1-pyrene)butyric acid N-hydroxysuccinimide ester 
• 200554-19-4 7-amino-3-((((succinimidyl)oxy)carbonyl)methyl)-4-methylcoumarin-6-sulfonic acid 
• 1206209-82-6 C₁₆H₁₂N₂O₅S 
• 944275-14-3 2-(2,3-dichloro-phenyl)-thiazole-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester 

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.