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

  • Boc-L-Ala-Bt

       
    Formula C14H18N4O3
    M.W. 290,32 g/mol
    Art-No Qty Price
    BAAX001.0005 5 g €175.00
    BAAX001.0025 25 g €650.00
  • Boc-L-Arg(Tos)-Bt

       
    Formula C24H31N7O5S
    M.W. 529,61 g/mol
    Art-No Qty Price
    BAAX016.0005 5 g €175.00
    BAAX016.0025 25 g €650.00
  • Boc-L-Asn-Bt

       
    Formula C15H19N5O4
    M.W. 333,34 g/mol
    Art-No Qty Price
    BAAX007.0005 5 g €175.00
    BAAX007.0025 25 g €650.00
  • Boc-L-Asp(Bzl)-Bt

       
    Formula C22H24N4O5
    M.W. 424,45 g/mol
    Art-No Qty Price
    BAAX015.0005 5 g €175.00
    BAAX015.0025 25 g €650.00
  • Boc-L-Cys(Bzl)-Bt

       
    Formula C21H24N4O3S
    M.W. 412,51 g/mol
    Art-No Qty Price
    BAAX019.0000 0 €0.00
  • Boc-L-Glu(Bzl)-Bt

       
    Formula C23H26N4O5
    M.W. 438,48 g/mol
    Art-No Qty Price
    BAAX014.0005 5 g €175.00
    BAAX014.0025 25 g €650.00
  • Boc-L-Gln-Bt

       
    Formula C16H21N5O4
    M.W. 347,37 g/mol
    Art-No Qty Price
    BAAX008.0005 5 g €175.00
    BAAX008.0025 25 g €650.00
  • Boc-Gly-Bt

       
    Formula C13H16N4O3
    M.W. 276,29 g/mol
    Art-No Qty Price
    BAAX009.0005 5 g €175.00
    BAAX009.0025 25 g €650.00
  • Boc-L-His(Bzl)-Bt

       
    Formula C24H26N6O3
    M.W. 446,5 g/mol
    Art-No Qty Price
    BAAX018.0000 0 €0.00
  • Boc-L-Ile-Bt

       
    Formula C17H24N4O3
    M.W. 332,4 g/mol
    Art-No Qty Price
    BAAX003.0005 5 g €175.00
    BAAX003.0025 25 g €650.00
  • Boc-L-Leu-Bt

       
    Formula C17H24N4O3
    M.W. 332,4 g/mol
    Art-No Qty Price
    BAAX004.0005 5 g €175.00
    BAAX004.0025 25 g €650.00
  • Boc-L-Lys(Z)-Bt

       
    Formula C25H31N5O5
    M.W. 481,54 g/mol
    Art-No Qty Price
    BAAX013.0005 5 g €175.00
    BAAX013.0025 25 g €650.00
  • Boc-L-Met-Bt

       
    Formula C16H22N4O3S
    M.W. 350,44 g/mol
    Art-No Qty Price
    BAAX005.0005 5 g €175.00
    BAAX005.0025 25 g €650.00
  • Boc-L-Phe-Bt

       
    Formula C20H22N4O3
    M.W. 366,41 g/mol
    Art-No Qty Price
    BAAX006.0005 5 g €175.00
    BAAX006.0025 25 g €650.00
  • Boc-L-Pro-Bt

       
    Formula C16H20N4O3
    M.W. 316,36 g/mol
    Art-No Qty Price
    BAAX010.0005 5 g €175.00
    BAAX010.0025 25 g €650.00
  • Boc-L-Ser(Bzl)-Bt

       
    Formula C21H24N4O4
    M.W. 396,44 g/mol
    Art-No Qty Price
    BAAX012.0005 5 g €175.00
    BAAX012.0025 25 g €650.00
  • Boc-L-Thr(Bzl)-Bt

       
    Formula C22H26N4O4
    M.W. 410,47 g/mol
    Art-No Qty Price
    BAAX020.0005 5 g €175.00
    BAAX020.0025 25 g €650.00
  • Boc-L-Val-Bt

       
    Formula C16H22N4O3
    M.W. 318,37 g/mol
    Art-No Qty Price
    BAAX002.0005 5 g €175.00
    BAAX002.0025 25 g €650.00
  • Boc-L-Tyr(Bzl)-Bt

       
    Formula C27H28N4O4
    M.W. 472,54 g/mol
    Art-No Qty Price
    BAAX011.0005 5 g €175.00
    BAAX011.0025 25 g €650.00
  • Boc-L-Trp(For)-Bt

       
    Formula C23H23N5O4
    M.W. 433,46 g/mol
    Art-No Qty Price
    BAAX017.0005 5 g €175.00
    BAAX017.0025 25 g €650.00

Fmoc-Protected Amino Acids

  • Fmoc-L-Ala-Bt

       
    Formula C24H20N4O3
    M.W. 412,44 g/mol
    Art-No Qty Price
    FAAX020.0005 5 g €175.00
    FAAX020.0025 25 g €650.00
  • Fmoc-L-Arg(Pbf)-Bt

       
    Formula C40H43N7O6S
    M.W. 749,88 g/mol
    Art-No Qty Price
    FAAX035.0005 5 g €175.00
    FAAX035.0025 25 g €650.00
  • Fmoc-L-Asn(Trt)-Bt

       
    Formula C44H35NO4
    M.W. 697,78 g/mol
    Art-No Qty Price
    FAAX036.0000 0 €0.00
  • Fmoc-L-Asp(tBu)-Bt

       
    Formula C29H28N4O5
    M.W. 512,56 g/mol
    Art-No Qty Price
    FAAX032.0005 5 g €175.00
    FAAX032.0025 25 g €650.00
  • Fmoc-L-Cys(Trt)-Bt

       
    Formula C43H34N4O3S
    M.W. 686,82 g/mol
    Art-No Qty Price
    FAAX038.0000 0 €0.00
  • Fmoc-L-Glu(tBu)-Bt

       
    Formula C30H30N4O5
    M.W. 526,58 g/mol
    Art-No Qty Price
    FAAX033.0005 5 g €175.00
    FAAX033.0025 25 g €650.00
  • Fmoc-L-Gln(Trt)-Bt

       
    Formula C45H37N5O4
    M.W. 711,81 g/mol
    Art-No Qty Price
    FAAX037.0000 0 €0.00
  • Fmoc-Gly-Bt

    CAS-No 1082989-49-8
    Formula C23H18N4O3
    M.W. 398,41 g/mol
    Art-No Qty Price
    FAAX026.0005 5 g €175.00
    FAAX026.0025 25 g €650.00
  • Fmoc-L-His(Boc)-Bt

       
    Formula C32H30N6O5
    M.W. 578,62 g/mol
    Art-No Qty Price
    FAAX040.0000 0 €0.00
  • Fmoc-L-Leu-Bt

    CAS-No 1072840-99-3
    Formula C27H26N4O3
    M.W. 454,52 g/mol
    Art-No Qty Price
    FAAX023.0005 5 g €175.00
    FAAX023.0025 25 g €650.00
  • Fmoc-L-Ile-Bt

       
    Formula C27H26N4O3
    M.W. 454,52 g/mol
    Art-No Qty Price
    FAAX022.0005 5 g €175.00
    FAAX022.0025 25 g €650.00
  • Fmoc-L-Lys(Boc)-Bt

       
    Formula C32H35N5O5
    M.W. 569,65 g/mol
    Art-No Qty Price
    FAAX031.0005 5 g €175.00
    FAAX031.0025 25 g €650.00
  • Fmoc-L-Met-Bt

       
    Formula C26H24N4O3S
    M.W. 472,56 g/mol
    Art-No Qty Price
    FAAX024.0005 5 g €175.00
    FAAX024.0025 25 g €650.00
  • Fmoc-L-Phe-Bt

       
    Formula C30H24N4O3
    M.W. 488,54 g/mol
    Art-No Qty Price
    FAAX025.0005 5 g €175.00
    FAAX025.0025 25 g €650.00
  • Fmoc-L-Ser(tBu)-Bt

       
    Formula C28H28N4O4
    M.W. 484,55 g/mol
    Art-No Qty Price
    FAAX029.0005 5 g €175.00
    FAAX029.0025 25 g €650.00
  • Fmoc-L-Pro-Bt

    CAS-No 1155875-68-5
    Formula C26H22N4O3
    M.W. 438,48 g/mol
    Art-No Qty Price
    FAAX027.0005 5 g €175.00
    FAAX027.0025 25 g €650.00
  • Fmoc-L-Thr(tBu)-Bt

       
    Formula C29H30N4O4
    M.W. 498,57 g/mol
    Art-No Qty Price
    FAAX030.0005 5 g €175.00
    FAAX030.0025 25 g €650.00
  • Fmoc-L-Trp(Boc)-Bt

       
    Formula C37H33N5O5
    M.W. 627,69 g/mol
    Art-No Qty Price
    FAAX034.0005 5 g €175.00
    FAAX034.0025 25 g €650.00
  • Fmoc-L-Val-Bt

       
    Formula C26H24N4O3
    M.W. 440,49 g/mol
    Art-No Qty Price
    FAAX021.0005 5 g €175.00
    FAAX021.0025 25 g €650.00
  • Fmoc-L-Tyr(tBu)-Bt

    CAS-No 1126433-42-8
    Formula C34H32N4O4
    M.W. 560,64 g/mol
    Art-No Qty Price
    FAAX028.0005 5 g €175.00
    FAAX028.0025 25 g €650.00

Z-Protected Amino Acids

  • Z-L-Ala-Bt

    CAS-No 820239-42-7
    Formula C17H16N4O3
    M.W. 324,33 g/mol
    Art-No Qty Price
    ZAAX040.0001 1 g €300.00
    ZAAX040.0005 5 g €1,200.00
  • Z-L-Asn-Bt

       
    Formula C18H17N5O4
    M.W. 367,36 g/mol
    Art-No Qty Price
    ZAAX048.0001 1 g €300.00
    ZAAX048.0005 5 g €1,200.00
  • Z-L-Gln-Bt

       
    Formula C19H19N5O4
    M.W. 381,39 g/mol
    Art-No Qty Price
    ZAAX049.0001 1 g €300.00
    ZAAX049.0005 5 g €1,200.00
  • Z-L-Leu-Bt

       
    Formula C20H22N4O3
    M.W. 366,41 g/mol
    Art-No Qty Price
    ZAAX043.0001 1 g €300.00
    ZAAX043.0005 5 g €1,200.00
  • Z-L-Ile-Bt

    CAS-No 1072442-07-9
    Formula C20H22N4O3
    M.W. 366,41 g/mol
    Art-No Qty Price
    ZAAX042.0001 1 g €300.00
    ZAAX042.0005 5 g €1,200.00
  • Z-Gly-Bt

    CAS-No 173459-80-8
    Formula C16H14N4O3
    M.W. 310,31 g/mol
    Art-No Qty Price
    ZAAX046.0001 1 g €300.00
    ZAAX046.0005 5 g €1,200.00
  • Z-L-Val-Bt

    CAS-No 820239-44-9
    Formula C19H20N4O3
    M.W. 352,39 g/mol
    Art-No Qty Price
    ZAAX041.0001 1 g €300.00
    ZAAX041.0005 5 g €1,200.00
  • Z-L-Pro-Bt

       
    Formula C19H18N4O3
    M.W. 350,37 g/mol
    Art-No Qty Price
    ZAAX047.0001 1 g €300.00
    ZAAX047.0005 5 g €1,200.00
  • Z-L-Phe-Bt

    CAS-No 769922-77-2
    Formula C23H20N4O3
    M.W. 400,43 g/mol
    Art-No Qty Price
    ZAAX045.0001 1 g €300.00
    ZAAX045.0005 5 g €1,200.00
  • Z-L-Met-Bt

       
    Formula C19H20N4O3S
    M.W. 384,45 g/mol
    Art-No Qty Price
    ZAAX044.0001 1 g €300.00
    ZAAX044.0005 5 g €1,200.00

Available Biotinylating Reagent Superior to Biotin-NHS:

  • Biotin cadaverine nTFA

    CAS-No 115416-38-1 net
    Formula C15H28N4O2S nC2HF3O2
    M.W. 328,47 net g/mol
    Art-No Qty Price
    RL-2030.0100 100 mg €84.00
    RL-2030.0250 250 mg €140.00
    RL-2030.0500 500 mg €252.00
    RL-2030.0001 1 g €392.00
    RL-2030.0005 5 g €1,400.00
  • Biotin-NHNH2

       
    Formula C10H18N4O2S
    M.W. 258,34 g/mol
    Art-No Qty Price
    LS-X051.0001 1 g €250.00
    LS-X051.0005 5 g €900.00
  • Biotin-OSu

    CAS-No 35013-72-0
    Formula C14H19N3O5S
    M.W. 341,39 g/mol
    Art-No Qty Price
    RL-1006.0001 1 g €85.00
    RL-1006.0005 5 g €300.00
    RL-1006.0025 25 g €1,200.00
  • Biotin-Bt

       
    Formula C16H19N5O2S
    M.W. 345,52 g/mol
    Art-No Qty Price
    LS-X050.0001 1 g €200.00
    LS-X050.0005 5 g €600.00