Nigerotriose is a trisaccharide composed of three D-glucose units linked by α-(1→3) glycosidic bonds, with the molecular formula C₁₈H₃₂O₁₆ and a molecular weight of 504.4 g/mol. It exists as a high-purity powder (>95%) and serves as a substrate for enzymes such as endo-1,3-α-glucanase and mutanase. Found in plants, fungi, and bacteria, it belongs to the family of neutral oligosaccharides.

Chemical Structure

Nigerotriose's systematic name is 3-O-α-D-glucopyranosyl-3-O-α-D-glucopyranosyl-D-glucopyranose, forming a linear chain: α-D-Glcp-(1→3)-α-D-Glcp-(1→3)-D-Glcp. Its stereochemistry follows the InChI notation specifying alpha configurations at key linkages, with computed properties such as XLogP3-AA indicating hydrophilicity. Derivatives like oxime-TMS isomers are used in structural analysis via mass spectrometry.

Biological Occurrence and Role

Nigerotriose occurs naturally in microbial and plant sources, functioning within carbohydrate metabolism and serving as a substrate in enzymatic assays. It interacts with glycoside hydrolases, including GH31 family enzymes, whose crystal structures reveal binding sites for nigerooligosaccharides. This makes it a valuable model compound for studying fungal cell wall degradation and oligosaccharide recognition.

Preparation and Applications

We provide nigerotriose for biochemical research, enzyme assays, and analytical testing. It can be prepared through enzymatic synthesis or isolated from natural sources. Its availability supports studies in carbohydrate fragmentation and structural characterization using IR photothermal methods. Additionally, nigerotriose is used to investigate prebiotic potential and glucanase specificity.