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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 Code

11 - Combustible Solids

WGK

WGK 2

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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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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