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- Name help_outline N,N'-diacetylchitobiose Identifier CHEBI:28681 (Beilstein: 1443239; CAS: 35061-50-8) help_outline Charge 0 Formula C16H28N2O11 InChIKeyhelp_outline CDOJPCSDOXYJJF-CBTAGEKQSA-N SMILEShelp_outline CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 8 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:35051 | RHEA:35052 | RHEA:35053 | RHEA:35054 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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The chitin catabolic cascade in the marine bacterium Vibrio furnissii. Characterization of an N,N'-diacetyl-chitobiose transport system.
Keyhani N.O., Wang L.X., Lee Y.C., Roseman S.
The disaccharide N,N'-diacetyl-chitobiose, (GlcNAc)2, is critical in chitin dissimilation by Vibrio furnissii and, as reported here, is taken up by a specific permease. Since (GlcNAc)2 is rapidly catabolized by V. furnissii, a non-hydrolyzable thioglycoside analogue was used: methyl beta-N,N'-[3H] ... >> More
The disaccharide N,N'-diacetyl-chitobiose, (GlcNAc)2, is critical in chitin dissimilation by Vibrio furnissii and, as reported here, is taken up by a specific permease. Since (GlcNAc)2 is rapidly catabolized by V. furnissii, a non-hydrolyzable thioglycoside analogue was used: methyl beta-N,N'-[3H]diacetyl-thiochitobioside (Me-[3H]TCB). Me-TCB and TCB substitute for (GlcNAc)2 as chemoattractants and inducers of beta-N-acetylglucosaminidase activity. The [3H]Me-TCB uptake system was induced only by (GlcNAc)2 and by (GlcNAc)n that can be converted to (GlcNAc)2. The Km for [3H]Me-TCB uptake was </=1 microM and was not affected by Na+ or K+. Uptake appeared to be unidirectional, and in 0.4 M sucrose (+/-K+) the cells accumulated [3H]Me-TCB until it was depleted from the medium, giving an internal concentration of 0.1 M and an internal/external ratio > 1,000. The only effective inhibitors of uptake were: (GlcNAc)n, n = 2-4 > cellobiose > (GlcNAc)5. In 50% artificial sea water (or sucrose/Na+), [3H]Me-TCB accumulation attained a constant steady state level because of efflux, a Na+-dependent process. The physiological implications of these results are considered. << Less