X-GlcA CHA Salt - ≥99% , CAS No.114162-64-0

CAS: 114162-64-0 Cat. No.: B104857 Molecular Weight: 521.8 EC Number: 601-302-0 PubChem CID: 2733578

GRADE & PURITY ≥99%

Synonyms

5-Bromo-4-chloro-3-indolyl-B-D-glucuronic acid cyclohexylammonium salt | cyclohexanamine (2S,3S,4S,5R,6S)-6-(5-bromo-4-chloro-1H-indol-3-yloxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate | X-Gluc (cyclohexanamine) | Cyclohexanamine(2S,3S,4S,5R,6S)-

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

X-GlcA is a chromogenic substrate for β-galactosidase, used to determine the presence or absence of a cloned DNA insert in bacteria growing on agar plates. X-GlcA is designed to replace X-Gal in blue-white selection of recombinant bacterial colonies with the lac+ phenotype. When X-GlcA is hydrolyzed by β-galactosidase, the resulting product will form a blue precipitate. Lac+ colonies grown in the presence of X-GlcA turn an intense blue color, allowing for easy differentiation between lac+ and lac- colonies.
Chromogenic substrate for β-glucuronidase (GUS) gene detection. Suitable for use in selection of recombinant bacterial colonies with the lac+ phenotype.

Specifications

Synonyms

5-Bromo-4-chloro-3-indolyl-B-D-glucuronic acid cyclohexylammonium salt | cyclohexanamine (2S, 3S, 4S, 5R, 6S)-6-(5-bromo-4-chloro-1H-indol-3-yloxy)-3, 4, 5-trihydroxytetrahydro-2H-pyran-2-carboxylate | X-Gluc (cyclohexanamine) | Cyclohexanamine(2S, 3S, 4S, 5R, 6S)-

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Chromogenic substrate for β-glucuronidase that is converted by the enzyme into an intense blue prepicitate. Used for the detection of the Gus gene in bacterial colonies.

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: C1CCC(CC1)N.C1=CC(=C(C2=C1NC=C2OC3C(C(C(C(O3)C(=O)O)O)O)O)Cl)Br
• IUPAC Name: (2S,3S,4S,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid;cyclohexanamine
• InChIKey: JXCKZXHCJOVIAV-CYRSAHDMSA-N
• INCHI: 1S/C14H13BrClNO7.C6H13N/c15-4-1-2-5-7(8(4)16)6(3-17-5)23-14-11(20)9(18)10(19)12(24-14)13(21)22;7-6-4-2-1-3-5-6/h1-3,9-12,14,17-20H,(H,21,22);6H,1-5,7H2/t9-,10-,11+,12-,14+;/m0./s1
• Isomeric SMILES: C1CCC(CC1)N.C1=CC(=C(C2=C1NC=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O)Cl)Br
• WGK Germany: 3
• PubChem CID: 2733578
• Molecular Weight: 521.8

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Sugar acids and derivatives
          • Level6 Glucuronic acid derivatives
            • Level7 Glucuronides
              • Level8 O-glucuronides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Sugar acids and derivatives - Glucuronic acid derivatives - Glucuronides
• Direct Parent: O-glucuronides
• Alternative Parents: Hexoses O-glycosyl compounds Indoles Cyclohexylamines Beta hydroxy acids and derivatives Substituted pyrroles Pyrans Oxanes Aryl bromides Aryl chlorides Benzenoids Heteroaromatic compounds Secondary alcohols Monocarboxylic acids and derivatives Azacyclic compounds Acetals Oxacyclic compounds Polyols Carboxylic acids Carbonyl compounds Hydrocarbon derivatives Monoalkylamines Organic oxides Organobromides Organochlorides Organopnictogen compounds
• Molecular Framework: Not available
• Substituents: O-glucuronide - 1-o-glucuronide - Hexose monosaccharide - O-glycosyl compound - Glycosyl compound - Indole or derivatives - Indole - Beta-hydroxy acid - Cyclohexylamine - Substituted pyrrole - Benzenoid - Hydroxy acid - Pyran - Monosaccharide - Aryl halide - Oxane - Aryl chloride - Aryl bromide - Heteroaromatic compound - Pyrrole - Secondary alcohol - Carboxylic acid derivative - Carboxylic acid - Polyol - Acetal - Monocarboxylic acid or derivatives - Oxacycle - Azacycle - Organoheterocyclic compound - Organobromide - Alcohol - Primary aliphatic amine - Primary amine - Organonitrogen compound - Organochloride - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Amine - Organohalogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Light ＆heat ＆air sensitive.
• Molecular Weight: 521.799 g/mol
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 520.061 Da
• Monoisotopic Mass: 520.061 Da
• Topological Polar Surface Area: 158.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 532.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3