Benzotriazole Amino Acids

Benzotriazole Amino Acids

Published on 18.06.2014

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:

  • 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.

 

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  • 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: