Benzotriazol activated carboxylic acids:

• Fast reaction (within minutes) at room temperature with amines and other nucleophiles under addition of base (in both water and non- aqueous solvents).
• Stable to racemization when coupling with nucleophiles.
• High solubility in organic solvents like DMF and DCM.
• Stable in water.

Benzotriazol activated carboxylic acids are very versatile building blocks for the preparation of a variety of carbonyl derivatives.

• They have proven to be outstandingly useful for the synthesis of primary, secondary, and tertiary amides, of depsipeptides and oligoesters, and in particular of difficult peptide sequences.
• Chemical ligation and other difficult conjugates can be synthesized with high yield and purity.
• Benzotriazoles (Bt) are a superior alternative to formerly used NHS (N-hydroxysuccinimide) and Pfp (pentafluorophenol) esters.
• Benzotriazoles (Bt) have a significant difference to N-hydroxybenzotriazoles (HOBt)! The latter ones are being prepared with potentially explosive HOBt and are rather instable, while Benzotriazole (Bt) compounds are very stable and not hazardous, at all.

Custom Synthesis Service

• Synthesis and antibacterial evaluation of amino acid–antibiotic conjugates; Mohamed A. Ibrahim, Siva S. Panda, Antoinette S. Birs, Juan C. Serrano, Claudio F. Gonzalez, Khalid A. Alamry, Alan R. Katritzky; Bioorganic & Medicinal Chemistry Letters 2014; 24: 1856-1861.
• N-Acylbenzotriazoles: neutral acylating reagents for the preparation of primary, secondary, and tertiary amides; Alan R. Katritzky, Hai-Ying He, Kazuyuki Suzuki; J. Org. Chem. 2000; 65(24): 8210-3.
• Total synthesis of cyclic heptapeptide Rolloamide; Mirna El Khatib, Mohamed Elagawany, Eray Çalis-kan, Emily Faith Davis, Hassan M. Faidallah, Said A. El-feky, Alan R. Katritzky; Chem. Commun. 2013; 49: 2631.
• Microwave-Assisted Solid-Phase Peptide Synthesis Utilizing N-Fmoc-Protected (alpha-aminoacyl)benzotriazoles; Alan R. Katritzky, Niveen M. Khashab, Megumi Yoshioka, Danniebelle N. Haase, Krista R. Wilson, Jodie V. Johnson, Alfred Chung, Carrie Haskell-Luevano; Chem. Biol Drug. Des. 2007; 70: 465- 468.
• N-Tfa- and N-Fmoc-(alpha-aminoacyl)benzotriazoles as Chiral C-Acylating Reagents under Friedel-Crafts Reaction Conditions; Alan R. Katritzky, Rong Jiang, Kazuyuki Suzuki; J. Org. Chem. 2005; 70: 4993-5000.
• Benzotriazole-Mediated Syntheses of Depsipeptides and Oligoesters; Ilker Avan, Srinivasa R. Tala, Peter J. Steel, Alan R. Katritzky; J. Org. Chem. 2011; 76: 4884–4893. dx.doi.org/10.1021/jo200174j.
• Chemical Ligation of S-Acylated Cysteine Peptides to Form Native Peptides via 5-, 11-, and 14-Membered Cyclic Transition States; Alan R. Katritzky, Srinivasa R. Tala, Nader E. Abo-Dya, Tarek S. Ibrahim, Said A. El-Feky, Kapil Gyanda, Keyur M. Pandya; J. Org. Chem. 2011; 76: 85-96; DOI: 10.1021/jo1015757.
• Benzotriazole-Assisted Solid-Phase Assembly of Leu-Enkephalin, Amyloid segment 34-42, and other “Difficult” Peptide Sequences; Alan R. Katritzky, Danniebelle N. Haase, Jodie V. Johnson, Alfred Chung; J. Org. Chem. 2009; 74: 2028-2032; DOI: 10.1021/jo8026214.
• The Efficient Preparation of Di- and Tripeptides by Coupling N-(Cbz- or Fmoc-alpha-aminoacyl)benzotriazoles with Unprotected Amino Acids; Alan R. Katritzky, Parul Angrish, Kazuyuki Suzuki; Synthesis 2006; 3: 411–424; DOI: 10.1055/s-2006-926287.

Available N-alpha-Protected Amino Acids:

Boc-Protected Amino Acids

Fmoc-Protected Amino Acids

Z-Protected Amino Acids

Available Biotinylating Reagent Superior to Biotin-NHS: