Sugar amino acids in designing new molecules

Abstract

Emulating the basic principles followed by nature to build its vast repertoire of biomolecules, organic chemists are developing many novel multifunctional building blocks and using them to create 'nature-like' and yet unnatural organic molecules. Sugar amino acids constitute an important class of such polyfunctional scaffolds where the carboxyl, amino and hydroxyl termini provide an excellent opportunity to organic chemists to create structural diversities akin to Nature's molecular arsenal. This article describes some of our works on various sugar amino acids and many other related building blocks, like furan amino acids, pyrrole amino acids etc. used in wide-ranging peptidomimetic studies.

Ferrocenyl-Labeled Sugar Amino Acids: Conformation and Properties

“…Sugar amino acids (SAAs) are hybrids of carbohydrates and amino acids featuring both the sugar framework and the amino and acid functional groups . SAAs play a significant role in peptidomimetic studies . SAAs containing protected rigid furan and pyran rings are also suitable for incorporation into peptides, acting as nonpeptidic scaffolds in the resulting peptidomimetics.…”

Conformational Analysis of Some C2-Symmetric Cyclic Peptides Containing Tetrahydrofuran Amino Acids

“…Since they were first reported, as useful peptide building blocks, the pyranoid and furanoid sugar amino acids have been used extensively by many research groups worldwide as conformationally constrained scaffolds in peptidomimetic studies. They form an important class of synthetic monomers, leading to many de novo oligomeric libraries, and versatile multifunctional templates, to create many designer molecules .…”

Classification of conformation for sugar amino acid systems using chiroptical spectroscopy

“…[1][2][3][4][5] Found in nature, SAAs are most common as construction elements (such as in cell walls) but also as components in bacterial antigens and in families of nucleoside antibiotics. 3,4 The structural and stereochemical diversity of saccharides (mono-, di-, etc.)…”