ECMDB: Chitobiose (ECMDB03556) (M2MDB000515)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)Transporters (7)XML

Proteins (383)

Record Information

Version

2.0

Creation Date

2012-05-31 13:59:51 -0600

Update Date

2015-10-15 16:15:08 -0600

Secondary Accession Numbers

ECMDB03556

Identification

Name:

Chitobiose

Description

Chitobiose is a dimer of beta-1,4-linked glucosamine units. There is ambiguity as to which structure the name refers, owing to the method by which it was first isolated.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-(acetylamino)-4-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-2-deoxy-β-D-glucopyranose
2-(acetylamino)-4-O-[2-(acetylamino)-2-Deoxy-b-D-glucopyranosyl]-2-deoxy-b-D-glucopyranose
2-(Acetylamino)-4-O-[2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]-2-deoxy-beta-D-glucopyranose
2-(acetylamino)-4-O-[2-(acetylamino)-2-Deoxy-β-D-glucopyranosyl]-2-deoxy-β-D-glucopyranose
N-[2-[5-acetylamino-4,6-dihydroxy-2-(hydroxymethyl)tetrahydropyran-3-yl]oxy-4,5-dihyrdoxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
CBS
Chitobiose
Chitodextrin
Diacetylchitobiose
N-[2-[5-Acetylamino-4,6-dihydroxy-2-(hydroxymethyl)tetrahydropyran-3-yl]oxy-4,5-dihyrdoxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide

Chemical Formula:

C₁₆H₂₈N₂O₁₁

Weight:

Average: 424.403
Monoisotopic: 424.16930973

InChI Key:

CDOJPCSDOXYJJF-CBTAGEKQSA-N

InChI:

InChI=1S/C16H28N2O11/c1-5(21)17-9-13(25)14(8(4-20)27-15(9)26)29-16-10(18-6(2)22)12(24)11(23)7(3-19)28-16/h7-16,19-20,23-26H,3-4H2,1-2H3,(H,17,21)(H,18,22)/t7-,8-,9-,10-,11-,12-,13-,14-,15?,16+/m1/s1

CAS number:

577-76-4

IUPAC Name:

N-[(3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Traditional IUPAC Name:

N,N-diacetylchitobiose

SMILES:

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
N-acyl-alpha-hexosamine
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Alcohol
Primary alcohol
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N,N'-diacetylchitobioses (CHEBI:28681 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	111 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-5.3	ChemAxon
logS	-0.58	ALOGPS
pKa (Strongest Acidic)	11.5	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	207.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.54 m³·mol⁻¹	ChemAxon
Polarizability	40.89 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Phosphoenolpyruvic acid + Chitobiose > Diacetylchitobiose-6-phosphate + Pyruvic acid
Chitobiose + Water <>2 N-Acetyl-D-glucosamine
Phosphoenolpyruvic acid + Chitobiose > Pyruvic acid + Diacetylchitobiose-6-phosphate
Water + Chitobiose + Chitobiose >2 N-Acetyl-D-glucosamine +2 N-Acetylglucosamine
Chitin + Water > Chitobiose + Chitin + Chitobiose
Chitobiose + Water <>2 N-Acetyl-D-glucosamine
Chitobiose + Water <>2 N-Acetyl-D-glucosamine

SMPDB Pathways:

Amino sugar and nucleotide sugar metabolism I	PW000886
Amino sugar and nucleotide sugar metabolism II	PW000887
Amino sugar and nucleotide sugar metabolism III	PW000895

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k96-5349200000-6b7d2bcfb4fbd50331f4	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-004i-4721139000-3735bfc0b00e29dea82b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_34) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_43) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_52) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_17) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_42) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_6_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_43) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_66) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("N,N'-diacetylchitobiose,3TMS,#34" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05rr-0026900000-234a7b9c8b9b6152b864	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-106r-1579300000-750b558d01585ab37fcc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0jbc-8966000000-8a7bb423f3a5855ac001	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-2392000000-aef5ce0ce16c169e7e1b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0r6r-6689300000-15c809a0c92d0bccf212	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-7940000000-3f8ef93cad595d7f6bf4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0kdi-0140900000-08169eb3826952ff0489	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2964300000-62211ded60815e3aeb97	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w9u-9610000000-109c16c31489f133e426	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0029200000-82938f4246a60c02ab2e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-7159100000-0b0f9e2ded83e4f0d508	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9252000000-d1e8391914a4500428fb	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Collin M, Olsen A: EndoS, a novel secreted protein from Streptococcus pyogenes with endoglycosidase activity on human IgG. EMBO J. 2001 Jun 15;20(12):3046-55. Pubmed: 11406581
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Nimtz M, Grabenhorst E, Gambert U, Costa J, Wray V, Morr M, Thiem J, Conradt HS: In vitro alpha1-3 or alpha1-4 fucosylation of type I and II oligosaccharides with secreted forms of recombinant human fucosyltransferases III and VI. Glycoconj J. 1998 Sep;15(9):873-83. Pubmed: 10052591
van Pelt J, Hard K, Kamerling JP, Vliegenthart JF, Reuser AJ, Galjaard H: Isolation and structural characterization of twenty-one sialyloligosaccharides from galactosialidosis urine. An intact N,N'-diacetylchitobiose unit at the reducing end of a diantennary structure. Biol Chem Hoppe Seyler. 1989 Mar;370(3):191-203. Pubmed: 2713102
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Cottaz, Sylvain; Samain, Eric. Genetic engineering of Escherichia coli for the production of NI,NII-diacetylchitobiose (chitinbiose) and its utilization as a primer for the synthesis of complex carbohydrates. Metabolic Engineering (2005), 7(4), 311

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	28681
HMDB ID	HMDB03556
Pubchem Compound ID	656440
Kegg ID	C01674
ChemSpider ID	17216232
Wikipedia	Chitobiose
BioCyc ID	CHITOBIOSE
EcoCyc ID	CHITOBIOSE

Enzymes

Protein Details

1. Phosphoenolpyruvate-protein phosphotransferase

General function:: Involved in transferase activity, transferring phosphorus-containing groups
Specific function:: General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:: ptsI
Uniprot ID:: P08839
Molecular weight:: 63561

Reactions

Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.

Protein Details

2. Probable bifunctional chitinase/lysozyme

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Bifunctional enzyme with lysozyme/chitinase activity
Gene Name:: chiA
Uniprot ID:: P13656
Molecular weight:: 97057

Reactions

Random hydrolysis of N-acetyl-beta-D-glucosaminide (1->4)-beta-linkages in chitin and chitodextrins.
Hydrolysis of (1->4)-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in a peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrins.

Protein Details

3. Beta-hexosaminidase

General function:: Involved in beta-N-acetylhexosaminidase activity
Specific function:: Cleaves GlcNAc linked beta-1,4 to MurNAc tripeptides
Gene Name:: nagZ
Uniprot ID:: P75949
Molecular weight:: 37594

Reactions

Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides.

Transporters

Protein Details

1. Probable bifunctional chitinase/lysozyme

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Bifunctional enzyme with lysozyme/chitinase activity
Gene Name:: chiA
Uniprot ID:: P13656
Molecular weight:: 97057

Reactions

Random hydrolysis of N-acetyl-beta-D-glucosaminide (1->4)-beta-linkages in chitin and chitodextrins.
Hydrolysis of (1->4)-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in a peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrins.

Protein Details

2. Sugar efflux transporter C

General function:: Involved in transmembrane transport
Specific function:: Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs
Gene Name:: setC
Uniprot ID:: P31436
Molecular weight:: 43493

Protein Details

3. N,N'-diacetylchitobiose permease IIC component

General function:: Involved in sugar:hydrogen symporter activity
Specific function:: The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in N,N'-diacetylchitobiose transport
Gene Name:: chbC
Uniprot ID:: P17334
Molecular weight:: 48332

Protein Details

4. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

5. Outer membrane pore protein E

General function:: Involved in transporter activity
Specific function:: Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:: phoE
Uniprot ID:: P02932
Molecular weight:: 38922

Protein Details

6. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

7. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

Chitobiose (ECMDB03556) (M2MDB000515)

Structure for #<Compound:0x7375718c>

Enzymes

Reactions

Reactions

Reactions

Transporters

Reactions