General description
TBTU and HBTU are two of the most popular in situ activation reagents used in solid phase and solution phase peptide synthesis [1,2,3,4,5,6,7,8,9]. These reagents offer reactivity similar to symmetrical anhydrides and BOP [1]. Couplings proceed smoothly and rates can even be enhanced by the addition of HOBt [2,4,5,6]. In addition to having high reactivity, TBTU and HBTU have also been shown to limit enantiomerization during fragment condensation and during DMAP catalyzed esterification of arginine derivatives [3]. Comparative experiments between HBTU and TBTU have shown that the counter ion has no influence on coupling rates or levels of enantiomerization [1].
Associated Protocols and Technical Articles
Guide to Selection of Coupling Reagents
Literature 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.
Linkage
Replaces: 01-62-0010
Analysis Note
Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Legal Information
Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany
- UPC:
- 41115701
- Condition:
- New
- Weight:
- 1.00 Ounces
- HazmatClass:
- No
- WeightUOM:
- LB
- MPN:
- 8510060025