TSTU

Structural formula
General
Surname	TSTU
other names	O - ( N -Succinimidyl) - N , N , N ′, N ′ -tetramethyluronium tetrafluoroborate
Molecular formula	C 9 H 16 BF 4 N 3 O 3
External identifiers / databases
EC number	629-651-4
ECHA InfoCard	100.157.815
PubChem	24864036
Wikidata	Q27926570
properties
Molar mass	301.05 g mol −1
Physical state	firmly
Melting point	198-201 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N , N , N ', N ' -Tetramethyl- O - ( N -succinimidyl) uronium tetrafluoroborate is a coupling reagent from the group of uronium salts. TSTU is water soluble, which is why it is used for peptide synthesis , crosslinking and immobilization of proteins . The immobilization cantake placeon silica gel , among other things. TSTU is based on HOSu . It is used in peptide synthesis for thelow- racemization coupling of N -methylated amino acids . With TSTU also be glycoconjugates produced.

Individual evidence

↑ ^a ^b ^c ^d data sheet N, N, N ′, N′-Tetramethyl-O- (N-succinimidyl) uronium tetrafluoroborate, 97% from Sigma-Aldrich , accessed on October 27, 2016 ( PDF ).
↑ M. Werner, A. Heil, N. Rothermel, H. Breitzke, PB Groszewicz, AS Thankamony, T. Gutmann, G. Buntkowsky: Synthesis and solid state NMR characterization of novel peptide / silica hybrid materials. In: Solid state nuclear magnetic resonance. Volume 72, November 2015, pp. 73-78, doi: 10.1016 / j.ssnmr.2015.09.008 , PMID 26411982 .
↑ ^a ^b Y. Nishiyama, S. Ishizuka, T. Mori, K. Kurita: O- (N-succinimidyl) -1,1,3,3-tetramethyluronium tetrafluoroborate-N-hydroxysuccinimide-CuCl2: a facile and reliable system for racemization-free coupling of peptides having a carboxy-terminal N-methylamino acid. In: Chemical & pharmaceutical bulletin. Volume 48, Number 3, March 2000, pp. 442-444, PMID 10726875 .
↑ M. Andersson, S. Oscarson, L. Ohberg: Synthesis of oligosaccharides with oligoethylene glycol spacers and their conversion into glycoconjugates using N, N, N ', N'-tetramethyl (succinimido) uronium tetrafluoroborate as coupling reagent. In: Glycoconjugate journal. Volume 10, Number 6, December 1993, pp. 461-465, PMID 8173338 .

[Sigma-1] ta sheet N, N, N ′, N′-Tetramethyl-O- (N-succinimidyl) uronium tetrafluoroborate, 97% from Sigma-Aldrich , accessed on October 27, 2016 ( PDF ).

[2] M. Werner, A. Heil, N. Rothermel, H. Breitzke, PB Groszewicz, AS Thankamony, T. Gutmann, G. Buntkowsky: Synthesis and solid state NMR characterization of novel peptide / silica hybrid materials. In: Solid state nuclear magnetic resonance. Volume 72, November 2015, pp. 73-78, doi: 10.1016 / j.ssnmr.2015.09.008 , PMID 26411982 .

[Nishiyama-3] Y. Nishiyama, S. Ishizuka, T. Mori, K. Kurita: O- (N-succinimidyl) -1,1,3,3-tetramethyluronium tetrafluoroborate-N-hydroxysuccinimide-CuCl2: a facile and reliable system for racemization-free coupling of peptides having a carboxy-terminal N-methylamino acid. In: Chemical & pharmaceutical bulletin. Volume 48, Number 3, March 2000, pp. 442-444, PMID 10726875 .

[4] M. Andersson, S. Oscarson, L. Ohberg: Synthesis of oligosaccharides with oligoethylene glycol spacers and their conversion into glycoconjugates using N, N, N ', N'-tetramethyl (succinimido) uronium tetrafluoroborate as coupling reagent. In: Glycoconjugate journal. Volume 10, Number 6, December 1993, pp. 461-465, PMID 8173338 .