HBTU

Structural formula
	HBTU ( O -form)
General
Surname	HBTU
other names	3- [bis (dimethylamino) methyliumyl] -3 H -benzotriazole-1-oxide-hexafluorophosphate; 2- (1 H -Benzotriazol-1-yl) -1,1,3,3-tetramethyluronium hexafluorophosphate;
Molecular formula	C 11 H 16 F 6 N 5 OP
External identifiers / databases
EC number	619-076-7
ECHA InfoCard	100.133.815
PubChem	2733084
Wikidata	Q19787025
properties
Molar mass	379.24 g mol −1
Physical state	firmly
Melting point	200 ° C (decomposition)
safety instructions
H and P phrases	H: 315-317-319-334-335
	P: 261-280-284-304-305-311-338-340-342-351
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

HBTU (2- (1 H -Benzotriazol-1-yl) -1,1,3,3-tetramethyluronium-hexafluorophosphate) is a coupling reagent which is used in peptide synthesis to generate peptides .

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

HBTU can exist in two forms, the uronium salt ( O form) or the preferred but less reactive iminium salt ( N form):

HBTU ( N -form)

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet HBTU ≥98.0% (T) from Sigma-Aldrich , accessed on April 21, 2015 ( PDF ).
^ 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 .
^ Solange Adam: HBTU: a mild activating agent of muramic acid. In: Bioorganic & Medicinal Chemistry Letters. 2, 1992, p. 571, doi : 10.1016 / S0960-894X (01) 81199-9 .
↑ 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 .
↑ Iman Abdelmoty, Fernando Albericio u. a .: Structural studies of reagents for peptide bond formation: Crystal and molecular structures of HBTU and HATU. In: Letters in Peptide Science. 1, 1994, p. 57, doi : 10.1007 / BF00126274 .

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet HBTU ≥98.0% (T) from Sigma-Aldrich , accessed on April 21, 2015 ( PDF ).

[DOI10.1016/S0040-4039%2800%2999616-3-2] 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 .

[DOI10.1016%2FS0960-894X%2801%2981199-9-3] Solange Adam: HBTU: a mild activating agent of muramic acid. In: Bioorganic & Medicinal Chemistry Letters. 2, 1992, p. 571, doi : 10.1016 / S0960-894X (01) 81199-9 .

[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 .

[DOI10.1007/BF00126274-7] Iman Abdelmoty, Fernando Albericio u. a .: Structural studies of reagents for peptide bond formation: Crystal and molecular structures of HBTU and HATU. In: Letters in Peptide Science. 1, 1994, p. 57, doi : 10.1007 / BF00126274 .