A New Conformationally Restricted Mimetic of Dipeptide EG – Synthesis of an Analogue of FEG | Zendy

Galeazzi Roberta | Zendy; Martelli Gianluca | Zendy; Marcucci Eleonora | Zendy; Mobbili Giovanna | Zendy; Natali Desiré | Zendy; Orena Mario | Zendy; Rinaldi Samuele | Zendy

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A New Conformationally Restricted Mimetic of Dipeptide EG – Synthesis of an Analogue of FEG

Author(s) -

Galeazzi Roberta,

Martelli Gianluca,

Marcucci Eleonora,

Mobbili Giovanna,

Natali Desiré,

Orena Mario,

Rinaldi Samuele

Publication year - 2007

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200700300

Subject(s) - chemistry , dipeptide , tripeptide , stereochemistry , alkylation , ethyl bromoacetate , protecting group , peptide , organic chemistry , catalysis , biochemistry , alkyl

Starting from the chiral pyrrolidin‐2‐one 2 , the carboxy group at C‐4 underwent homologation, and subsequent removal of the 1‐(4‐methoxyphenyl)ethyl group gave lactam 6 . Alkylation of N‐1 with benzyl bromoacetate led to 7 , a new conformationally restricted analogue of the dipeptide EG (Glu‐Gly). The usefulness of 7 was demonstrated by its eventual conversion into 8 , an orthogonally protected analogue ofbioactive tripeptide FEG. In order to provide the biological activity of the new mimetic 9 , available from 8 after the removal of the protecting groups, the conformational preference of 9 was ascertained by a detailed conformational analysis and a comparison with that of FEG ( 1 ). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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