O-(1,2-dihydro-2-oxo-pyridyl)-1,1,3,3-tetramethyluronium tetrafluoroborate
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O-(1,2-dihydro-2-oxo-pyridyl)-1,1,3,3-tetramethyluronium tetrafluoroborate

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It is a coupling agent for peptide synthesis and is particularly suitable for fragment condensation without racemization.

Category
Peptide Synthesis Reagents
Catalog number
BAT-002369
CAS number
125700-71-2
Molecular Formula
C10H16N3O2.BF4
Molecular Weight
297.06
O-(1,2-dihydro-2-oxo-pyridyl)-1,1,3,3-tetramethyluronium tetrafluoroborate
IUPAC Name
[dimethylamino-(2-oxopyridin-1-yl)oxymethylidene]-dimethylazanium;tetrafluoroborate
Synonyms
TPTU; 2-(2-Pyridon-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate; O-(2-Oxo-1(2H)pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; o-(1,2-dihydro-2-oxo-1-pyridyl)-n,n,n',n'-tetramethyluronium tetrafluoroborate; MFCD00075475; AK170016; Methanaminium, N-[(dimethylamino)[(2-oxo-1(2H)-pyridinyl)oxy]methylene]-N-methyl-, tetrafluoroborate(1-) (1:1)
Appearance
White crystalline
Purity
99 % (HPLC)
Melting Point
140 ℃ (dec.)
Storage
2-8 ℃
Solubility
Insoluble in water
InChI
InChI=1S/C10H16N3O2.BF4/c1-11(2)10(12(3)4)15-13-8-6-5-7-9(13)14;2-1(3,4)5/h5-8H,1-4H3;/q+1;-1
InChI Key
CZQGINAUZYECAI-UHFFFAOYSA-N
Canonical SMILES
[B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C=CC=CC1=O
1. Improved method for preparing N-hydroxysuccinimide ester-containing polymers for affinity chromatography
M Wilchek, K L Knudsen, T Miron Bioconjug Chem. 1994 Sep-Oct;5(5):491-2. doi: 10.1021/bc00029a018.
N,N,N',N'-Tetramethyl(succinimido) uronium tetrafluoroborate is proposed as a reagent of choice for the activation of carboxyl groups and formation of N-hydroxysuccinimide esters on polymers. Unlike conventional methods which generate unstable gels, the reaction is appropriate for hydroxy-containing resins like Sepharose, cellulose, and dextran. The yields of activation and subsequent coupling capacity for ligands and proteins are very high. The respective columns can be used for affinity chromatography and immobilization of proteins.
2. Synthesis of oligosaccharides with oligoethylene glycol spacers and their conversion into glycoconjugates using N,N,N',N'-tetramethyl(succinimido)uronium tetrafluoroborate as coupling reagent
M Andersson, S Oscarson, L Ohberg Glycoconj J. 1993 Dec;10(6):461-5. doi: 10.1007/BF00737967.
Glycosides of glucose and lactose with di- and tetraethylene glycols, transformed into bifunctional (alcohol, ester) spacer molecules, have been synthesized. After deprotection, these spacer glycosides, containing a free carboxyl group, have been transformed efficiently into glycoconjugates using N,N,N',N'-tetramethyl(succinimido)uronium tetrafluoroborate (TSTU) for the formation of an active ester.
3. [2-Chloro-1-methylpyridinium iodide. A suitable reagent for peptide synthesis]
W Keese, H Khalaf, D Grambow, G Grundke, M Rimpler Biol Chem Hoppe Seyler. 1985 Dec;366(12):1093-5.
2-Chloro-1-methylpyridinium iodide is a coupling reagent for peptide synthesis. By its use different peptides were synthesized with protected di- and trifunctional amino acids. While urethan-protected amino acids react free of racemization, the fragment condensation needs N-Hydroxysuccinimide, as shown by the Young test.
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