Целлобионолактон

Description

Cellobionolactone (cellobionic acid cerbionolactone) is a disaccharide lactone, a product of the enzymatic oxidation of cellobiose. It is a D-glucono-1,5-lactone with a beta-D-glucosyl residue in the 4-position. It is formed by the action of the enzyme cellobiose dehydrogenase (CDH), which oxidizes cellobiose with the concomitant reduction of the cofactor FAD to FADH2.

Basic Attributes

• CAS No.: 52762-22-8
• Chemical formula: C12H20O11
• Molecular weight: 340.281
• Exact weight: 340.28
• NSC Number: 196590/14980
• PSA Specifications: 186
• XLogP3: -4.2

Chemical structure

The systematic name is 4-O-β-D-glucopyranosyl-D-gluconic acid δ-lactone, also referred to as cellobiono-1,5-lactone and cellobioso-1,5-lactone. The molecule consists of two hexose residues connected by a β-1,4-glycosidic bond, with lactonization of the reducing end in the form of a five-membered δ-lactone ring.

Biological role and production

A key intermediate product in the cellobiose dehydrogenase system, an extracellular hemoflavoprotein of brown and white rot fungi, which is involved in the degradation of cellulose and lignin. The reaction of cellobiose oxidation to cellobionolactone with the reduction of FAD to FADH2 is associated with the transfer of electrons to ligninolytic enzymes and is part of the fungal mechanism for the decomposition of lignocellulosic biopolymer.

Scope of application

Used as a substrate and reference compound in enzyme chemistry in the study of cellobiose dehydrogenase and biomass degradation processes; is considered as a building block for biomedical polymer scaffolds based on modified cellobiose derivatives, including azido derivatives.

Storage and transportation conditions

Store in an airtight container in a dry, cool place, protected from moisture - like a sugar lactone, the compound is hygroscopic and prone to hydrolysis upon contact with water, opening the lactone ring back to the corresponding acid. Work in clean, dry containers, avoid long-term storage of open solutions.

Additionally

Cellobiose dehydrogenase, which produces cellobionolactone, belongs to the extracellular hemoflavoproteins and is synthesized by brown and white rot fungi (in particular, Phanerochaete chrysosporium and Sclerotium rolfsii) as part of the extracellular redox apparatus of wood decomposition. In addition to cellobiose, the enzyme is capable of oxidizing related azido derivatives of the disaccharide at the C1 position, which is used in the design of modified polymer materials.

Identification

In biochemical ontology databases, the compound is registered under the number ChEBI 17863 and the Wikidata code Q27102668, which makes it possible to unambiguously link data from different sources when working with enzymatic literature on cellulose degradation. Azide derivatives of cellobioses, oxidized by the same enzyme to the corresponding lactones, are used in click reaction chemistry to obtain labeled and functionalized polysaccharide fragments.