HCTU

Structural formula
General
Surname	HCTU
other names	(2- (6-chloro-1 H -benzotriazol-1-yl) -1,1,3,3-tetramethylaminium hexafluorophosphate); O - (6-chlorobenzotriazol-1-yl) - N , N , N ′, N ′ -tetramethyluronium hexafluorophosphate; 1- [bis (dimethylamino) methylene] -5-chlorobenzotriazolium 3-oxide hexafluorophosphate; N , N , N ', N ' -Tetramethyl- O - (6-chloro-1 H -benzotriazol-1-yl) uronium hexafluorophosphate;
Molecular formula	C 11 H 15 ClF 6 N 5 OP
Brief description	White dust
External identifiers / databases
EC number	608-825-3
ECHA InfoCard	100.116.975
Wikidata	Q20054524
properties
Molar mass	413.7 g mol −1
Physical state	firmly
Melting point	185-190 ° C
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

HCTU (2- (6-chloro-1 H -benzotriazole-1-yl) -1,1,3,3-tetramethylaminium hexafluorophosphate) is a coupling agent , which in the peptide synthesis for the production of peptides is used.

The coupling of activated amino acids with peptides using HCTU as an auxiliary reagent proceeds with little racemization and takes two minutes. Alternative coupling reagents are e.g. B. HATU , HBTU , TBTU , COMU , TOMBU and COMBU .

Individual evidence

↑ ^a ^b ^c ^d Data sheet O- (6-Chlorobenzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium hexafluorophosphate ≥98.0% (HPLC) from Sigma-Aldrich , accessed on May 19, 2017 ( PDF ) .
↑ CA Chantell, MA Onaiyekan, M. Menakuru: Fast conventional Fmoc solid-phase peptide synthesis: a comparative study of different activators. In: Journal of Peptide Science . Volume 18, Number 2, February 2012, pp. 88-91, doi : 10.1002 / psc.1419 , PMID 22147296 .
^ Reinhard Knorr, Arnold Trzeciak, Willi Bannwarth, Dieter Gillessen: New coupling reagents in peptide chemistry. In: Tetrahedron Letters . 30, 1989, p. 1927, doi : 10.1016 / S0040-4039 (00) 99616-3 .
↑ CU Hjørringgaard, A. Brust, PF Alewood: Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis. In: Journal of Peptide Science. Volume 18, Number 3, March 2012, pp. 199-207, doi : 10.1002 / psc.1438 , PMID 22252935 .
↑ R. Subirós-Funosas, L. Nieto-Rodriguez, KJ Jensen, F. Albericio: COMU: scope and limitations of the latest innovation in peptide acyl transfer reagents. In: Journal of Peptide Science. Volume 19, Number 7, July 2013, pp. 408-414, doi : 10.1002 / psc.2517 , PMID 23712932 .
↑ YE Jad, SN Khattab, BG de la Torre, T. Govender, HG Kruger, A. El-Faham, F. Albericio: TOMBU and COMBU as Novel Uronium-type peptide coupling reagents derived from Oxyma-B. In: Molecules. Volume 19, number 11, 2014, pp. 18953-18965, doi : 10.3390 / molecules191118953 , PMID 25412042 .

[Sigma-1] Data sheet O- (6-Chlorobenzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium hexafluorophosphate ≥98.0% (HPLC) from Sigma-Aldrich , accessed on May 19, 2017 ( PDF ) .

[2] CA Chantell, MA Onaiyekan, M. Menakuru: Fast conventional Fmoc solid-phase peptide synthesis: a comparative study of different activators. In: Journal of Peptide Science . Volume 18, Number 2, February 2012, pp. 88-91, doi : 10.1002 / psc.1419 , PMID 22147296 .

[DOI10.1016/S0040-4039%2800%2999616-3-3] Reinhard Knorr, Arnold Trzeciak, Willi Bannwarth, Dieter Gillessen: New coupling reagents in peptide chemistry. In: Tetrahedron Letters . 30, 1989, p. 1927, doi : 10.1016 / S0040-4039 (00) 99616-3 .

[4] CU Hjørringgaard, A. Brust, PF Alewood: Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis. In: Journal of Peptide Science. Volume 18, Number 3, March 2012, pp. 199-207, doi : 10.1002 / psc.1438 , PMID 22252935 .

[5] R. Subirós-Funosas, L. Nieto-Rodriguez, KJ Jensen, F. Albericio: COMU: scope and limitations of the latest innovation in peptide acyl transfer reagents. In: Journal of Peptide Science. Volume 19, Number 7, July 2013, pp. 408-414, doi : 10.1002 / psc.2517 , PMID 23712932 .

[6] YE Jad, SN Khattab, BG de la Torre, T. Govender, HG Kruger, A. El-Faham, F. Albericio: TOMBU and COMBU as Novel Uronium-type peptide coupling reagents derived from Oxyma-B. In: Molecules. Volume 19, number 11, 2014, pp. 18953-18965, doi : 10.3390 / molecules191118953 , PMID 25412042 .