D-Luciferin-6-O-β-D-galactopyranoside - ≥98% , CAS No.131474-38-9

CAS: 131474-38-9 Cat. No.: D275740 Molecular Weight: 442.47 PubChem CID: 193947

GRADE & PURITY ≥98%

Synonyms

6-O-beta-D-galactopyranosyl-luciferin | Luciferin-O-galactopyranoside | Luciferin-O-gal | 2-[6-(Hexopyranosyloxy)-1,3-benzothiazol-2-yl]-4,5-dihydro-1,3-thiazole-4-carboxylic acid | (4S)-2-[6-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]o

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Application

Enzyme activity assay

Overview

Shipped at 4°C. Store at -20°C. Store under desiccating conditions.

Specifications

Synonyms

6-O-beta-D-galactopyranosyl-luciferin | Luciferin-O-galactopyranoside | Luciferin-O-gal | 2-[6-(Hexopyranosyloxy)-1, 3-benzothiazol-2-yl]-4, 5-dihydro-1, 3-thiazole-4-carboxylic acid | (4S)-2-[6-[(2S, 3R, 4S, 5R, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]o

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Ultrasensitive chemiluminescent beta-galactosidase substrate. D-luciferin analog with beta-galactoside on 6-O position. Beta-galactoside must be hydrolysed by beta-galactosidase before luciferin can be acted on by firefire luciferase.

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Note

Refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1C(N=C(S1)C2=NC3=C(S2)C=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)C(=O)O
• IUPAC Name: (4S)-2-[6-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3-benzothiazol-2-yl]-4,5-dihydro-1,3-thiazole-4-carboxylic acid
• InChIKey: OUKXHVUTHGDBNY-VEAFCXQSSA-N
• INCHI: 1S/C17H18N2O8S2/c20-4-9-11(21)12(22)13(23)17(27-9)26-6-1-2-7-10(3-6)29-15(18-7)14-19-8(5-28-14)16(24)25/h1-3,8-9,11-13,17,20-23H,4-5H2,(H,24,25)/t8-,9-,11+,12+,13-,17-/m1/s1
• Isomeric SMILES: C1[C@@H](N=C(S1)C2=NC3=C(S2)C=C(C=C3)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)C(=O)O
• PubChem CID: 193947
• Molecular Weight: 442.47

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Phenolic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Phenolic glycosides
• Alternative Parents: Hexoses O-glycosyl compounds Alpha amino acids and derivatives Benzothiazoles Oxanes Imidothiolactones Benzenoids Thiazolines Thiazoles Heteroaromatic compounds Secondary alcohols Propargyl-type 1,3-dipolar organic compounds Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Acetals Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenolic glycoside - Hexose monosaccharide - O-glycosyl compound - Alpha-amino acid or derivatives - 1,3-benzothiazole - Imidothiolactone - Benzenoid - Oxane - Monosaccharide - Heteroaromatic compound - Meta-thiazoline - Thiazole - Azole - Secondary alcohol - Oxacycle - Azacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Polyol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Acetal - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Primary alcohol - Organonitrogen compound - Carbonyl group - Alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
• 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

• Solubility: Soluble in water
• Molecular Weight: 442.500 g/mol
• XLogP3: 0.400
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 5
• Exact Mass: 442.05 Da
• Monoisotopic Mass: 442.05 Da
• Topological Polar Surface Area: 215.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 655.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• 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: 1