An improved procedure for the synthesis of dehydroamino acids and dehydropeptides from the carbonate derivatives of serine and threonine using tetrabutylammonium fluoride.
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 and without side reactions are limited. We report here an improved procedure for the synthesis of dehydroalanine and dehydroamino butyric acid from the carbonate derivatives of serine and threonine using TBAF. The antiselective E(2) elimination of the carbonate derivatives of serine and threonine using TBAF is milder and more efficient than other available procedures. The elimination reaction is completed in less than 10 min with various carbonate derivatives studied and the methodology is very efficient for the synthesis of dehydroamino acids and dehydropeptides. The procedure thus provides an easy access to key synthetic precursors and can be used to introduce interesting structural elements to designed peptides.
Ramapanicker
Ramesh
R
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
Mishra
Roli
R
Chandrasekaran
Srinivasan
S
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012694:Serine / Q000737:chemistry*; D013912:Threonine / Q000737:chemistry*; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D002254:Carbonates; D010455:Peptides; D000644:Quaternary Ammonium Compounds; D013912:Threonine; D012694:Serine; D005680:gamma-Aminobutyric Acid; C081919:alpha, beta-dehydroaminobutyric acid; C015102:dehydroalanine; C009405:tetrabutylammonium; D000409:Alanine