Description

• 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 ArticlesGuide to Selection of Coupling ReagentsLiterature 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.
• Application: Synthesis of Quinoxaline Derivatives Using HBTU: A study highlighting the use of HBTU as a Lewis acid catalyst for synthesizing quinoxaline derivatives, presenting a mild and green protocol (Popatkar and Meshram, 2020). Efficient Conversion of Carboxylic Acids into Benzimidazoles: Details an HBTU-promoted methodology for converting carboxylic acids into benzimidazoles in a one-pot strategy (Barasa and Yoganathan, 2018). Synthesis of Malonyl-linked Glycoconjugates: Discusses the use of HBTU in the synthesis of glycoconjugates, comparing its efficiency with other reagents (Nörrlinger et al., 2016).
• Linkage: Replaces: 01-62-0010
• Analysis Note: Colour (visual): white to slight yellow to beigeAppearance of substance (visual): powderIdentity (IR): passes testAssay (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