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Sigma-Aldrich

Thiocellobiose

≥98.0% (TLC)

Synonym(s):

4-S-β-D-glucopyranosyl-4-thio-D-glucose

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About This Item

Empirical Formula (Hill Notation):
C12H22O10S
CAS Number:
80951-92-4
Molecular Weight:
358.36
MDL number:
MFCD00270082
UNSPSC Code:
12352201
PubChem Substance ID:
329751924
NACRES:
NA.25

Assay

≥98.0% (TLC)

form

solid

technique(s)

thin layer chromatography (TLC): suitable

storage temp.

−20°C

SMILES string

OC[C@@H](O)[C@@H](S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)C=O

InChI

1S/C12H22O10S/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h1,4-12,14-21H,2-3H2/t4-,5+,6+,7+,8+,9-,10+,11+,12-/m0/s1

InChI key

VMEDEPBFFWJMMG-WELRSGGNSA-N

Application

Thiocellobiose is a glucose disaccharide linked via a β(1-4) thioether bond. Thiocellobiose is a cellulase inducer and inhibitor useful to identify, differentiate and characterize cellobiose-active β-glucosidase(s). Thiocellobiose is also used as a substrate to identify, differentiate and characterize cellobiose dehydrogenase(s).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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U Baminger et al.
Applied and environmental microbiology, 67(4), 1766-1774 (2001-04-03)
Cellobiose dehydrogenase (CDH) is an extracellular hemoflavoenzyme produced by several wood-degrading fungi. In the presence of a suitable electron acceptor, e.g., 2,6-dichloro-indophenol (DCIP), cytochrome c, or metal ions, CDH oxidizes cellobiose to cellobionolactone. The phytopathogenic fungus Sclerotium rolfsii (teleomorph: Athelia
G Henriksson et al.
Biochimica et biophysica acta, 1383(1), 48-54 (1998-04-18)
Substrate structural mapping suggests that the catalytic site of cellobiose dehydrogenase from Phanerochaete chrysosporium forms a narrow cave with two hexose binding subsites. Kinetic data also show that beta-di or oligosaccharides are favored electron donors with respect to both KM
E Montero et al.
FEBS letters, 421(3), 243-248 (1998-02-19)
The conformation of 4-thiocellobiose bound to beta-glucosidase from Streptomyces sp. has been studied by 1H-NMR transferred nuclear Overhauser effect spectroscopy (TR-NOE). Thiocellobiose behaves as an inhibitor of this glucosidase when cellobiose is used as substrate. NOE measurements and molecular mechanics
Pablo Isorna et al.
Journal of molecular biology, 371(5), 1204-1218 (2007-06-26)
Bacteria species involved in degradation of cellulosic substrates produce a variety of enzymes for processing related compounds along the hydrolytic pathway. Paenibacillus polymyxa encodes two homologous beta-glucosidases, BglA and BglB, presenting different quaternary structures and substrate specificities. We previously reported
D Rho et al.
Journal of bacteriology, 149(1), 47-53 (1982-01-01)
Several mono-, di, tetra-, and polysaccharides were screened for their ability to induced cellulase production by the tetrapolar hymenomycete Schizophyllum commune. Out of 21 carbohydrates screened, 4 (thiocellobiose, carboxymethylcellulose, cellobiose, and xylan) induced all three enzymes tested (carboxymethylcellulase, beta-glucosidase, and
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