Question

Help with synthesis of Lumino!!

b. What is bioluminescence? How does it work? (Make sure you are specific with the structure of the compound and the name of the enzyme that creatures produce) Draw the full electron pushing mechanism for the synthesis of the starting material you use in this C. reaction, 3-nitrophthalhydrazide, from 3-nitrophthalic acid and hydrazine. HINT: this is an acyl substitution reaction between a carboxylic acid and amine functionality Chromatographic Features Comparisons: (5 points) 3. Predict the order that the starting material and the product would appear on a TLC plate by drawing spots on the provided TLC plate below to indicate relative Rf values Explain and justify your answer thoroughly with words using the polarity factors covered on page 99-100 of the lab guide. 3-nitrophthalhydrazide (Lane A): A B Luminol product (Lane B)

Answer 1

Bioluminescence is the emission of visible light by biological systems, which arises from enzyme-catalyzed chemical reactions. Bioluminescence can be distinguished from chemiluminescence in that it occurs in living organisms and requires an enzyme catalyst. Bioluminescence has been observed in many organisms and phyla throughout the terrestrial and aquatic worlds, with the majority of luminescent organisms being found in the ocean.

Bioluminescence reaction in fireflies is given below.


Luminescent species are found among marine and terrestrial bacteria, annelids or segmented worms (e.g., fireworms), beetles (e.g., fireflies, click beetles, railroad worms), algae (e.g., dinoflagellates)

HO H AMP AMP DLuciferin - PPi ATP - AMP Light CO2 + +

Luminol (C₈H₇N₃O₂) is a chemical that exhibits chemiluminescence, with a blue glow, when mixed with an appropriate oxidizing agent. Luminol is a white-to-pale-yellow crystalline solid that is soluble in most polar organic solvents, but insoluble in water. its structure is as below.

NH2 NH NH O

c. The synthesis of luminol is as follows

H-B ON HO O OH ON OH NH2 H H OH H NH OH H&N-NH hydrazine o'H ON ON ON NO NH N NH NH NH NH NH