Synthesis of 1,1-Dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) protected N-methyl amino acids by reduction of Bsmoc-5-oxazoli-dinones and their use in peptide synthesis.
Protein Pept Lett
; 16(2): 105-11, 2009.
Article
en En
| MEDLINE
| ID: mdl-19200031
ABSTRACT
The synthesis of Bsmoc-N-methyl amino acids is presented. The first step involves p-toluenesulfonic acid (TsOH) catalysed condensation of a Bsmoc-amino acid with paraformaldehyde to furnish N-Bsmoc-5-oxazolidinone under MW irradiation. This intermediate is reduced to the corresponding N-methyl amino acid using triethylsilane (Et3SiH) and trifluoroacetic acid (TFA) at r.t. The N-methyl amino acids are converted into corresponding acid fluorides using diethylaminosulfur trifluoride (DAST) and employed as coupling agents in the synthesis of dipeptides. The peptide coupling was mediated by KOAt in CH2Cl2.
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Banco de datos:
MEDLINE
Asunto principal:
Péptidos
/
Tiofenos
/
Oxazolidinonas
/
Aminoácidos
Idioma:
En
Año:
2009
Tipo del documento:
Article