2-Azidoethoxy derivatives of 2-aminocyclohexanecarboxylic acids (ACHC): interesting building blocks for the synthesis of cyclic -peptide conjugates

Academic Article

Publication Date:

2011

Citation:

2-Azidoethoxy derivatives of 2-aminocyclohexanecarboxylic acids (ACHC): interesting building blocks for the synthesis of cyclic -peptide conjugates / J.J. Reina Martín, A. Bernardi. - In: TETRAHEDRON. - ISSN 0040-4020. - 67:32(2011), pp. 5770-5775.

abstract:

Oligomers of cyclic beta-aminoacids possess a high resistance to peptidase-catalyzed
hydrolysis and display a high intrinsic tendency to adopt regular secondary structures. These
characteristics are attractive to develop new biologically active substances. However, cyclic-betapeptides
often show limited solubility in water and cannot be conjugated to biologically relevant
fragments, such as oligosaccharides, which are often essential for full biololgical activity of natural alfapeptides.
In this article, we report the synthesis of one trans- and one cis-2-aminocyclohexane
carboxylic acid (ACHC) both functionalized with a hydroxy group, to increase the solubility in water,
and an azidoethoxy group to allow the synthesis of cyclic-beta-peptide conjugates by a "click reaction"

IRIS type:

01 - Articolo su periodico

Keywords:

β-Aminoacids; Conjugates; Epoxidation; Stereoselective synthesis

List of contributors: