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

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Abstract:

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

Document Type: Research Article

DOI: https://doi.org/10.2174/092986612803521666

Publication date: 2012-12-01

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  • Protein & Peptide Letters publishes short papers in all important aspects of protein and peptide research, including structural studies, recombinant expression, function, synthesis, enzymology, immunology, molecular modeling, drug design etc. Manuscripts must have a significant element of novelty, timeliness and urgency that merit rapid publication. Reports of crystallisation, and preliminary structure determinations of biologically important proteins are acceptable. Purely theoretical papers are also acceptable provided they provide new insight into the principles of protein/peptide structure and function.
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