HBTU
Sign in to saveHBTU (hexafluorophosphate benzotriazole tetramethyl uronium) is a coupling reagent used in solid phase peptide synthesis. It was introduced in 1978 and shows resistance against racemization. It is used because of its mild activating properties.
Wikidata facts
- Mass
- 379.099666
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- chemical formula
- C₁₁H₁₆F₆N₅OP
- canonical SMILES
- CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
- Commons category
- HBTU
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HBTU (hexafluorophosphate benzotriazole tetramethyl uronium) is a coupling reagent used in solid phase peptide synthesis. It was introduced in 1978 and shows resistance against racemization. It is used because of its mild activating properties.
HBTU is prepared by reaction of hydroxybenzotriazole with TCFH under basic conditions and was assigned to a uronium type structure, presumably by analogy with the corresponding phosphonium salts, which bear a positive carbon atom instead of the phosphonium residue. Later, it was shown by X-ray analysis that salts crystallize as guanidinium rather than the corresponding uronium salts.