Chitobioses are a group of related

disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, lact ...

s of β-1,4-linked

glucosamine Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of two polysaccharides, chitosan and chitin. Glucosamine is one of the most ...

units. The term ''chitobiose'' is sometimes used to refer to different members of the group, depending on the method by which it was first isolated, resulting in some

ambiguity Ambiguity is the type of meaning in which a phrase, statement or resolution is not explicitly defined, making several interpretations plausible. A common aspect of ambiguity is uncertainty. It is thus an attribute of any idea or statement ...

as to which chemical compound the name is referring to. Chitobiose is the condensed form of 4‐''O''‐(2‐amino‐2‐deoxy‐β‐D‐glucopyranosyl)‐2‐amino‐2‐deoxy‐D‐glucose and is an

acetylation : In organic chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed ''acetate esters'' or simply '' acetates''. Deacetylation is the oppo ...

found in

chitin Chitin ( C8 H13 O5 N)n ( ) is a long-chain polymer of ''N''-acetylglucosamine, an amide derivative of glucose. Chitin is probably the second most abundant polysaccharide in nature (behind only cellulose); an estimated 1 billion tons of chit ...

. It is formed by the depolymerization of chitin either enzymatically or chemically. Chitobiose is utilized by ''

Borrelia burgdorferi ''Borrelia burgdorferi'' is a bacterial species of the spirochete class in the genus ''Borrelia'', and is one of the causative agents of Lyme disease in humans. Along with a few similar genospecies, some of which also cause Lyme disease, it make ...

'' to produce ''N''-acetylglucosamine, a component of the bacterial cell wall, and is regularized by the response regulator rrp1. A mutant strain of rrp1 has been found to cause growth deficits with ''Borrelia burgdorferi''. In ''

Escherichia coli ''Escherichia coli'' (),Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. also known as ''E. coli'' (), is a Gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus ''Escher ...

'', the chb operon is involved with the utilization of

cellobiose Cellobiose is a disaccharide with the formula (C6H7(OH)4O)2O. It is classified as a reducing sugar. In terms of its chemical structure, it is derived from the condensation of a pair of β-glucose molecules forming a β(1→4) bond. It can be hyd ...

and β-glucosides chitobiose. The chbG gene of the chb Operon encodes a chitooligosaccharide deacetylase. The ''chb'' operon is also responsible for coding the ''ChbR'' regulator, which is responsible for activating transcription when chitobiose is available.

References

{{Reflist Amino sugars Disaccharides

See also

References