Ribosomal Synthesis of Dehydroalanine-Containing Peptides
β Scribed by Seebeck, Florian P.; Szostak, Jack W.
- Book ID
- 121320087
- Publisher
- American Chemical Society
- Year
- 2006
- Tongue
- English
- Weight
- 78 KB
- Volume
- 128
- Category
- Article
- ISSN
- 0002-7863
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## Abstract __Michael acceptors have long been recognized as reactive functionalities that may link a biologically active molecule to its cellular target. 1,2βDehydro amino acids are potential Michael acceptors present in a large number of natural products, but their reactivity is modulated by the
A routine method for the synthesis of dehydroalanine containing peptides has been developed. These residues are introduced as S-methyl cysteines which are subsequently oxidised and eliminated. The approach is compatible with both Boc and Fmoc protection strategies and can allow the introduction of a
Three model dipeptides containing a dehydroalanine residue ( AAla) at the C-terminal, Boc-X-AAla-NHCH3 [ X = Ala, Val, and Phe,] have been synthesized and their solution conformations investigated by 'H-NMR, IR, and CD spectroscopy. NMR studies on these peptides in CDCl, clearly indicate that the NH