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(±)-3,5-Bis(substitutedmethyl)pyrrolidines: Application to the Synthesis of Analogues of glycine-L-proline-L-glutamic Acid (GPE)

Author(s):

Olga Caamaño*, Joana Ferreira, David Silva and Xerardo Garcia-Mera   Pages 1 - 7 ( 7 )

Abstract:


The tripeptide GPE is the naturally cleaved N-terminal tripeptide of insulin-like growth factor-1 (IGF-1) in brain tissues, therefore, GPE has been suggested to be a potential target for the rational design of neuroprotective agents. In this paper, we describe the synthesis of various scaffolds resembling to the proline by means of a diversity oriented, efficient synthetic strategy that drives to different functionalized proline-derivatives. Besides, a process for the synthesis of news analogues of the neuroprotective agent GPE by coupling sequence was developed. The utility of the racemic methyl (2RS,3SR,5RS)-3,5-bis(azidomethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylate (±1) and other derivatives as scaffolds in the preparation of small peptidomimetic analogues of GPE with potential pharmacological properties has been demonstrated through of the preparation of tripeptides 11.

Keywords:

proline derivatives; neuropeptides; GPE; azides; Staudinger–Vilarrasa coupling; synthesis.

Affiliation:

Universidade de Santiago de Compostela - Química Orgánica Santiago de Compostela, A Coruña, Universidade de Santiago de Compostela - Química Orgánica Santiago de Compostela, A Coruña, Universidade de Santiago de Compostela - Química Orgánica Santiago de Compostela, A Coruña, Universidade de Santiago de Compostela - Química Orgánica Santiago de Compostela, A Coruña



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