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Merck
CN

19608

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
NACRES:
NA.25
PubChem Substance ID:
329751924
UNSPSC Code:
12352201
MDL number:
MFCD00270082

Key Documents

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InChI key

VMEDEPBFFWJMMG-WELRSGGNSA-N

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

assay

≥98.0% (TLC)

form

solid

technique(s)

thin layer chromatography (TLC): suitable

storage temp.

−20°C

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.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCBR0785V
BCBP9230V
BCBP3626V
BCBM8058V
BCBL2938V

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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
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
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
Meera E Atreya et al.
Biotechnology and bioengineering, 113(2), 330-338 (2015-08-25)
Enzymes that degrade cellulose into glucose are one of the most expensive components of processes for converting cellulosic biomass to fuels and chemicals. Cellulase enzyme Cel7A is the most abundant enzyme naturally employed by fungi to depolymerize cellulose, and like
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