Products > Peptide Coupling Reagents > HBTU




HBTU
(2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate)

               CAS #:
94790-37-1
               Molecular Formula:
C11H16F6N5OP
               Molecular Weight:
379.3
               Melting Point:
203 - 204°C
               Appearance:
white powder
               Purity (HPLC):
≥99.00%


Catalog #
Quantity
Price (US $)
120802
25 g
15.00
100 g
25.00
500 g
100.00
1 kg
185.00


HBTU is one of the most popular in situ activation reagents used in solution phase and solid phase peptide synthesis for both t-butoxycarbonyl (Boc) and fluorenylmethoxycarbonyl (Fmoc) strategies. HBTU is also a convenient agent for the synthesis of tetramethylsulfonylguanidines in basic conditions. Couplings proceed smoothly and rates can even be enhanced by the addition of HOBt. In addition to having high reactivity, HBTU has also been shown to limit enantiomerization during fragment condensation and during DMAP catalyzed esterification of arginine derivatives. But lower yielding couplings can become problematic on industrial scales and with long peptides.

References

1. R. Knorr, et al. (1989) Tetrahedron Lett., 30, 1927.
2. M. S. Bernatowicz, et al. (1989) Tetrahedron Lett., 30, 4645.
3. D. Ambrosius, et al. (1989) Biol. Chem. Hoppe-Seyler, 370, 217.
4. C. G. Fields, et al. (1991) Pept. Res., 4, 95.
5. A. G. Beck-Sickinger, et al. (1991) Pept. Res., 4, 88.
6. G. E. Reid, et al. (1992) Anal. Biochem., 200, 301.
7. G. B. Fields, et al. in "Innovation & Perspectives in Solid Phase Synthesis, 1st International Symposium", R. Epton (Eds), SPCC UK Ltd., Birmingham, 1990, pp. 241.
8. P. A. Baybayan, et al. in "Peptides, Chemistry & Biology, Proc. 12th American Peptide Symposium", J. A. Smith & J. E. Rivier (Eds), ESCOM, Leiden, 1992, pp. 566.
9. J. J. Dudash, et al. (1993) Synth. Commun., 23, 349.
10. J. Comb. Chem. 2004, 6, 695
11. Org. Bio. Chem. 2010, 8, 835
12. Biopoly. 2006, 84, 340
13. Pept Res. 1991, 4, 95
14. Tetrahedron Lett. 2006, 47, 6087
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