Glyco Amino Acids

Introduction

Glyco amino acids are carbohydrate derivatives containing both amino and carboxylic acid functionalities. Glyco amino acids and their derivatives exist in various forms with various biological activities in nature. Recently, to meet the increasing demand for discovering new molecules entities to develop new drugs and materials, many unnatural glyco amino acids also have been designed and synthesized by many research groups. The stereochemical arrangement of the substituents of the sugar ring, its ring-size as well as the presence of additional functional groups provides a plethora of possible combinations.

Application

Building blocks: Anomeric glyco γ-amino acids are useful building blocks for the preparation of new cyclic glycopeptides, which have potential applications as templates for anchoring of a wide range of biomolecules or detection dyes. Pyranuronic β-glyco amino acids are biocompatible building blocks due to their adjustable properties in ring size, substituents, conformation, stereochemistry as well as adjustable amphiphilic character.

Medicines: Glucosaminuronic acid 1 and galactosaminuronic acid 2 are constituents of cell walls of many bacteria. They have been explored as potential vaccine antigens for influenza virus and Staphylococcus aureus prevention. Many of their analogues have been investigated as promising candidates for therapeutic agents recently.

Glyco Amino Acids

Scaffolds: Glyco amino acids are applied as scaffolds in combinatorial chemistry and in a template-directed synthesis of biopolymers.

Materials: Glyco amino acids represent an important class of new molecules with multifunctional groups anchored on a single of ensemble. They can be used to develop novel materials with potential applications as glycomimetics, artificial amino acids and peptidomimetics. The main benefit of using glyco amino acids and their related nitrogen and carbon congeners in the production of peptidomimetics and glycomimetics is that their properties can be readily altered via modification of their ring size, chemical manipulation of their numerous functional groups and fine-tuning of the stereochemical arrangement of their ring substituents.

Reference:

  1. Risseeuw MDP, Overhand M, Fleet GWJ, et al. A compendium of sugar amino acids (SAA): scaffolds, peptide- and glyco-mimetics. Tetrahedron-asymmeetry. 2007, 18(17): 2001-2010.
  2. Richard M, Ariztia J, Lamande-Langle S, et al. Sugar γ-Amino Acids as Building Blocks for the Synthesis of Cyclic Neoglycopeptides. Chemistryselect. 2018, 3(31): 9121-9126.
  3. Tian GZ, Hu J, Zhang HX, et al. Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs). Scientific Reports. 2018, 8: 6625.
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