Synthesis of novel sugar diamino acids

Sugar amino acids (SAAs) are found in nature as good construction elements for the preparation of peptide mimetics and oiigosaccharides in drug design and development. The synthesis of SAAs is readily accomplished in few steps and more than 40 SAAs have been synthesised to date.2 Sugar amino acids with an additional amino group, the sugar diamino acid (SDAs) would represent a useful expansion to the library of SAAs available because one of the amino group and carboxylic acid is available for peptide coupling and the another amino/azide group allow to do further derivatisation via peptide or click chemistry such as labelling. However, the synthesis of SDAs is challenging and only three general type have been reported to date.2 As part of a project involving the synthesiso f novel integrin antagonists, we require a new series of SDAs to be developed. Herein, the synthesis of the novel SDAs type 1 and 2 and their applications will be presented. Reference: (1) Gruner, S. A.; Locardi, E.; Lohof, E.; Kessler, H. Chemical Reviews 2002, 102, 491-514. (2) Risseeuw, M. D. P.; Overhand, M.; Fleet,G . W J.; Simone. M. I. Tetrahedron: Asymmetry 2007, 18, 2001-2010.