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Applications of the Mitsunobu reaction in peptide chemistry

✍ Scribed by Kazimierz Wiśniewski; Aleksandra S. Kołdziejczyk; Bogdan Falkiewicz

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
232 KB
Volume
4
Category
Article
ISSN
1075-2617

No coin nor oath required. For personal study only.

✦ Synopsis

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 b-hydroxy amino acid containing peptides under Mitsunobu reaction conditions leads to a constrained peptide that mimics the stabilizing reverse turn secondary structure.

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