140422-46-4Relevant articles and documents
An improved procedure for the synthesis of dehydroamino acids and dehydropeptides from the carbonate derivatives of serine and threonine using tetrabutylammonium fluoride
Ramapanicker, Ramesh,Mishra, Roli,Chandrasekaran, Srinivasan
, p. 123 - 125 (2010)
Dehydroamino acids are important precursors for the synthesis of a number of unnatural amino acids and are structural components in many biologically active peptide derivatives. However, efficient synthetic procedures for their production in large amounts
An efficient synthesis of dehydroamino acids and dehydropeptides from O-Cbz and O-Eoc derivatives of serine and threonine
Ramesh, Ramapanicker,De, Kavita,Chandrasekaran, Srinivasan
, p. 10534 - 10542 (2008/02/13)
A simple and efficient method for the synthesis of dehydroamino acids from serine and threonine is reported. Various O-Cbz and O-Eoc derivatives of serine and threonine are prepared using CbzCl and EocCl, respectively, and are subjected to an anti-selective elimination on treatment with K2CO3 in DMF at 65 °C to afford dehydroalanine and dehydroamino butyric acid derivatives, respectively, in excellent yields. The high stability of these carbonate derivatives of serine and threonine allows their use in normal peptide synthesis as protected serine and threonine residues. Peptides synthesized by incorporating O-Cbz or O-Eoc derivatives undergo ready elimination under the reported conditions, to give the corresponding dehydropeptides in excellent yields. The reaction conditions are mild enough not to cause the racemization of other stereogenic centers present in the peptide.
A detailed investigation of the preparation of 2,7-diaminosuberic acid and 2,5-diaminoadipic acid derivatives using Kolbe electrolysis
Hiebl, Johann,Blanka, Michael,Guttman, Andras,Kollmann, Hermann,Leitner, Kornelia,Mayrhofer, Guenter,Rovenszky, Franz,Winkler, Karin
, p. 2059 - 2074 (2007/10/03)
The yield of protected 2,7-diaminosuberic acid (DAS) prepared by Kolbe reaction of N-protected α-glutamic acid esters is dependent on solvent, temperature, concentration of carboxylate onion, and protecting groups. The highest yield of protected L,L-2,7-diaminosuberic acid is obtained with Boc-Glu-OMe as starting material using MeOH/pyridine/NaOMe as electrolyte.