4-Nitrophenyl-alpha-D-maltoheptaoside
[CAS# 74173-31-2]

Identification

• Classification: Biochemical >> Carbohydrate >> Oligosaccharide
• Name: 4-Nitrophenyl-alpha-D-maltoheptaoside
• Synonyms: (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• Molecular Formula: C₄₈H₇₅NO₃₈
• Molecular Weight: 1274.09
• CAS Registry Number: 74173-31-2
• EC Number: 277-741-3
• SMILES: C1=CC(=CC=C1[N+](=O)[O-])O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O[C@@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O[C@@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O

Properties

• Density: 1.9±0.1 g/cm³ Calc.^*
• Boiling point: 1498.2±65.0 ºC 760 mmHg (Calc.)^*
• Flash point: 859.9±34.3 ºC (Calc.)^*
• Index of refraction: 1.715 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

4-Nitrophenyl-α-D-maltoheptaoside is a synthetic glycoside in which a maltoheptaose chain, composed of seven D-glucose units linked via α-1,4-glycosidic bonds, is conjugated at the reducing end to a 4-nitrophenyl group. This structure combines a hydrophilic oligosaccharide moiety with a chromogenic aromatic group, making it highly useful in enzymology and carbohydrate research. The 4-nitrophenyl group acts as a leaving group that can be cleaved by specific glycosidases, releasing 4-nitrophenol, which is detectable by its characteristic absorbance in the visible range, facilitating quantitative enzymatic assays.

The synthesis of 4-nitrophenyl-α-D-maltoheptaoside typically involves selective glycosylation of the 4-nitrophenol with activated maltoheptaose derivatives. Glycosyl donors, such as trichloroacetimidate or bromide derivatives of maltoheptaose, are reacted under conditions that favor formation of the α-glycosidic linkage to the 4-nitrophenyl acceptor. Protecting groups on intermediate glucose units are carefully used to prevent side reactions and ensure regioselectivity. After the coupling reaction, global deprotection yields the final chromogenic substrate as a crystalline or amorphous solid.

In enzymology, 4-nitrophenyl-α-D-maltoheptaoside serves as a substrate for α-amylases, glucoamylases, and other glycosidases that act on α-1,4-linked glucose chains. Upon enzymatic hydrolysis, the release of 4-nitrophenol can be monitored spectrophotometrically, allowing precise measurement of enzyme activity, kinetics, and substrate specificity. Its defined heptaose chain length provides a controlled substrate to study chain-length preferences of enzymes and to evaluate inhibitors.

This compound is also valuable in carbohydrate research and synthetic chemistry. It can be used as a starting material for further derivatization, such as modification of the glucose units or conjugation to polymers, peptides, or other biomolecules. The chromogenic 4-nitrophenyl group provides a convenient handle for tracking reactions or for immobilization on solid supports in assays and bioanalytical applications.

Physically, 4-nitrophenyl-α-D-maltoheptaoside is typically obtained as a solid with good solubility in aqueous media and polar organic solvents such as dimethyl sulfoxide or methanol. It is stable under neutral to mildly acidic or basic conditions but should be protected from strong acids, strong bases, and light, which may cause hydrolysis or degradation of the nitrophenyl moiety. Proper storage ensures reproducible performance in enzymatic and analytical applications.

Overall, 4-nitrophenyl-α-D-maltoheptaoside is a chromogenic oligosaccharide derivative combining a maltoheptaose chain with a 4-nitrophenyl group. Its design allows selective enzymatic hydrolysis with spectrophotometric monitoring, making it an essential tool in enzymology, carbohydrate research, and bioanalytical chemistry.

References

2022. Characterization of an Amylolytic Enzyme from Massilia timonae of the GH13_19 Subfamily with Mixed Maltogenic and CGTase Activity. Applied Biochemistry and Biotechnology, 195(4).
DOI: 10.1007/s12010-022-04226-7

2021. Impact of exogenous maltogenic α-amylase and maltotetraogenic amylase on sugar release in wheat bread. European Food Research and Technology.
DOI: 10.1007/s00217-021-03721-1

2020. Impact of exogenous α-amylases on sugar formation in straight dough wheat bread. European Food Research and Technology.
DOI: 10.1007/s00217-020-03657-y