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Protein & Peptide Letters


ISSN (Print): 0929-8665
ISSN (Online): 1875-5305

(Acyloxy)Alkoxy Moiety as Amino Acids Protecting Group for the Synthesis of (R,R)-2,7 Diaminosuberic Acid via RCM

Author(s): Adriano Mollica, Federica Feliciani, Azzurra Stefanucci, Evgeny A. Fadeev and Francesco Pinnen

Volume 19, Issue 12, 2012

Page: [1245 - 1249] Pages: 5

DOI: 10.2174/092986612803521666

Price: $65


A new synthetic pathway is described to prepare asymmetrically protected 2,7-diaminosuberic acid. This strategy exploits (acyloxy)alkoxy promoiety as protecting group and RCM reaction using second generation Grubbs catalyst and provides the trans isomer of (2R,7R)-7-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(tert-butoxycarbonylamino)-8- methoxy-8-oxooct-4-enoic acid, which was in turn reduced to obtain (2R,7R)-7-(((9H-fluoren-9-yl)methoxy)carbonylamino)- 2-(tert-butoxycarbonylamino)-8-methoxy-8-oxooctanoic acid.

Keywords: Grubbs catalyst, ring closing metathesis, (acyloxy)alkoxy, diaminosuberic acid, orthogonal protecting groups, metabolism, prodrugs, C-terminal, diaminosuberic acid, ring closing metathesis (RCM).

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