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Dramatically enhanced N→O acyl migration during the trifluoroacetic acid-based deprotection step in solid phase peptide synthesis
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Feb2005, Vol. 46 Issue 8, p1361-1364. 4p. - Publication Year :
- 2005
-
Abstract
- Abstract: N→O acyl migrations at serine or threonine residues in peptides or proteins have previously been observed upon treatment with strong acids. Here we show that the extent of such N→O shifts depends on the peptide sequence and even in the presence of moderately acidic trifluoroacetic acid, as during Fmoc or Bsmoc-based solid phase peptide synthesis, may give rise to large amounts of depsipeptide by-products. [Copyright &y& Elsevier]
- Subjects :
- *PEPTIDE synthesis
*SERINE
*PROTEINS
*ACIDS
Subjects
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 46
- Issue :
- 8
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 16203626
- Full Text :
- https://doi.org/10.1016/j.tetlet.2004.12.089