ISSN:
1075-2617
Keywords:
Mitsunobu reaction
;
N-alkyl amino acid synthesis
;
amino acid derivatives synthesis
;
β-lactam formation
;
peptide oxazolines and thiazolines
;
Chemistry
;
Biochemistry and Biotechnology
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The Mitsunobu reaction - the nucleophilic substitution of an alcoholic hydroxyl group mediated by the redox system trialkylphosphine/dialkyl azodicarobxylate - is widely used in the chemistry of biologically active compounds. The paper deals with applications of the Mitsunobu reaction in amino acid and peptide chemistry. The process provides easy access to many unnatural amino acids and derivatives. Since the reaction occurs with complete inversion of the configuration at the carbinol chiral centre, it can be used for the synthesis of diastereoisomers of hydroxy- and tioprolines. Cyclization of β-hydroxy amino acid containing peptides under Mitsunobu reaction conditions leads to a constrained peptide that mimics the stabilizing reverse turn secondary structure. © 1998 European Peptide Society and John Wiley & Sons, Ltd.
Additional Material:
28 Ill.
Type of Medium:
Electronic Resource