What is the rule of attendance in HBTU

HBTU

HBTU (2-(1H-Benzotriazol-1-yl) -1,1,3,3-tetramethyluronium hexafluorophosphate) is a coupling reagent which is used in peptide synthesis to generate peptides.

The coupling of activated amino acids with peptides using HBTU as an auxiliary reagent proceeds with little racemization.[2] HBTU is a comparatively mild coupling reagent.[3] Alternative coupling reagents are e.g. B. HATU, HCTU,[4]TBTU, COMU,[5]TOMBU and COMBU.[6]

HBTU can exist in two forms, as the uronium salt (OForm) or as the preferred but less reactive iminium salt (N-Shape):[7]

Individual evidence

  1. abcdeData sheet HBTU ≥98.0% (T) from Sigma-Aldrich, accessed on April 21, 2015 (PDF).
  2. ↑ Reinhard Knorr, Arnold Trzeciak, Willi Bannwarth, Dieter Gillessen: New coupling reagents in peptide chemistry. In: Tetrahedron Letters. 30, 1989, p. 1927, doi: 10.1016 / S0040-4039 (00) 99616-3.
  3. ↑ As long as Adam: HBTU: a mild activating agent of muramic acid. In: Bioorganic & Medicinal Chemistry Letters. 2, 1992, p. 571, doi: 10.1016 / S0960-894X (01) 81199-9.
  4. ↑ C. U. Hjørringgaard, A. Brust, P. F. Alewood: Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis. In: Journal of Peptide Science. Volume 18, Number 3, March 2012, pp. 199-207, doi: 10.1002 / psc.1438, PMID 22252935.
  5. ↑ R. Subirós-Funosas, L. Nieto-Rodriguez, K. J. Jensen, F. Albericio: COMU: scope and limitations of the latest innovation in peptide acyl transfer reagents. In: Journal of Peptide Science. Volume 19, Number 7, July 2013, pp. 408-414, doi: 10.1002 / psc.2517, PMID 23712932.
  6. ↑ Y. E. Jad, S. N. Khattab, B. G. de la Torre, T. Govender, H. G. Kruger, A. El-Faham, F. Albericio: TOMBU and COMBU as Novel Uronium-type peptide coupling reagents derived from Oxyma-B. In: Molecules. Volume 19, number 11, 2014, pp. 18953-18965, doi: 10.3390 / molecules191118953, PMID 25412042.
  7. ↑ Iman Abdelmoty, Fernando Albericio et al .: Structural studies of reagents for peptide bond formation: Crystal and molecular structures of HBTU and HATU. In: Letters in Peptide Science. 1, 1994, p. 57, doi: 10.1007 / BF00126274.

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