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73837

Sigma-Aldrich

5-Bromo-4-chloro-3-indolyl α-D-glucopyranoside

≥98.0% (HPLC), powder

Synonym(s):

X-α-Glc, X-α-glucoside

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About This Item

Empirical Formula (Hill Notation):
C14H15BrClNO6
CAS Number:
108789-36-2
Molecular Weight:
408.63
MDL number:
MFCD00155606
UNSPSC Code:
12352204
PubChem Substance ID:
329765272
NACRES:
NA.32

product name

5-Bromo-4-chloro-3-indolyl α-D-glucopyranoside, ≥98.0% (HPLC)

assay

≥98.0% (HPLC)

form

powder

optical activity

[α]/D 105.0±5.0°, c = 1 in DMF/H2O 1:1

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@H](Oc2c[nH]c3ccc(Br)c(Cl)c23)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C14H15BrClNO6/c15-5-1-2-6-9(10(5)16)7(3-17-6)22-14-13(21)12(20)11(19)8(4-18)23-14/h1-3,8,11-14,17-21H,4H2/t8-,11-,12+,13-,14+/m1/s1

InChI key

OPIFSICVWOWJMJ-HRNXZZBMSA-N

General description

5-Bromo-4-chloro-3-indolyl α-D-glucopyranoside, X-Gluc, is a indigogenic substrate for β- glucuronidase enzyme (GUS). It aids screening of transgenic plants based on GUS activity. GUS deesterifies X-Gluc into indoxyl derivative which upon oxidative polymerization results in the generation of blue indigotin dye.

Application

suitable as substrate for α-glucosidase; substrate used in the Druggan-Forsythe-Iversen medium (DFI agar) for the selective detection of Enterobacter sakazakii in infant milk

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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A Histochemical Method Using a Substrate of. BETA.-Glucuronidase for Detection of Genetically Modified Papaya
Wakui C, et al.
Shokuhin Eiseigaku Zasshi, 45(1), 19-24 (2004)
B T Kinsella et al.
Current genetics, 20(1-2), 45-52 (1991-07-01)
The molecular cloning of an alpha-glucosidase gene isolated from a Candida tsukubaensis (CBS 6389) genomic library in Saccharomyces cervisiae is reported. The cloned gene is contained within a 6.2 kb Sau3A DNA fragment and directs the synthesis and secretion of
GUS fusions: beta-glucuronidase as a sensitive and versatile gene fusion marker in higher plants.
Jefferson RA, et al.
The Embo Journal, 6(13), 3901-3907 (1987)
Carol Iversen et al.
International journal of food microbiology, 96(2), 133-139 (2004-09-15)
Enterobacter sakazakii can cause fatal invasive infection of neonates associated with the presence of this organism in powdered infant milk formula. A new chromogenic medium (Druggan-Forsythe-Iversen agar, DFI) is described for the selective detection of this emergent pathogen. The medium
Functional insight for beta-glucuronidase in Escherichia coli and Staphylococcus sp. RLH1
Arul L, et al.
Bioinformation, 2(8), 339-339 (2008)

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