Q29-1P - Organic Chemistry (Mcmurry)

Question

PROBLEM 29-1One of the steps in fat metabolism is the reaction of glycerol (1,2,3-propane-triol) with ATP to yield glycerol 1-phosphate. Write the reaction, and draw thestructure of glycerol 1-phosphate.

Step-by-Step Solution

Answer

Here the reaction is,           ${\mathrm{HOCH}}_2\mathrm{CH}\left(\mathrm{OH}\right){\mathrm{CH}}_2\mathrm{OH}+\mathrm{ATP}\to {\mathrm{HOCH}}_2\mathrm{CH}\left(\mathrm{OH}\right){\mathrm{CH}}_2{\mathrm{OPO}}_3^{2-}+\mathrm{ADP}$ 

The structure of glycerol 1-phosphate as follows,

Introduction to the Concept

Adenosine triphosphate (ATP) is the "energy currency" of the cell in most food catabolism reactions.

Solution Explanation

The energy released to generate ATP from ADP and hydrogen phosphate ion catabolizes the process. Anabolic reactions then spend ATP by transferring a phosphate group to another molecule, regenerating ADP. As a result, energy production and usage in living organisms revolves upon $\mathrm{ATP}\stackrel{}{\leftrightarrows }\mathrm{ADP}$ interconversion.

Phosphate acid anhydrides, such as ADP and ATP, have links that are comparable to the connections found in carboxylic acid anhydrides. Phosphoric acid anhydrides react with alcohols by breaking a P-O link and generating a phosphate ester, ${\mathrm{ROPO}}_3^{2-}$ .

This phosphorylation is seen in the following reaction.

As a result, glycerol is a poly-ol, trihydrialcohol, with three OH groups in 1, 2, and 3 propanetriol.

The phosphorylation is formed at C-1 of the alcohol.

In terms of mechanism, the reaction is a nucleophilic acyl substitution at phosphorus. To create a Lewis-acid-base complex with the phosphate oxygen atoms and neutralise a negative charge, phosphorylation with ATP necessitates the presence of a divalent metal cation in the enzyme, usually ${\mathrm{Mg}}^{2+}$.

As a result, the process is a phosphorylation of glycerol at C-1.