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Solved: Show how to bring about each step in the following synthesis

Organic Chemistry | 7th Edition | ISBN: 9781133952848 | Authors: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote ISBN: 9781133952848 483

Solution for problem 23.47 Chapter 23

Organic Chemistry | 7th Edition

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Organic Chemistry | 7th Edition | ISBN: 9781133952848 | Authors: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Organic Chemistry | 7th Edition

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Problem 23.47

Show how to bring about each step in the following synthesis.

Step-by-Step Solution:
Step 1 of 3

CHEM 372 Week 3 Notes  4/12/16 Reaction 7  1,3-BPG to 3PG using PGK as the enzyme  Slightly exergonic but is the breaking even point of Glycolysis  Close to equilibrium  Uses protein dynamics to drive reaction. Push Pull reaction mech.  Forces phosphates together till they touch and react. Swap phosphates.  Similar to hexokinase mechanism  Active site of enzyme has Lysine that points towards BPG phosphate o Pulls electron density away from phosphate group on BPG o Oxygen on ADP phosphate attacks electrophilic phosphate on BPG o Transition state is the most energetically rich molecule o Lysine on enzyme stabilizes TS to speed up reaction o Substrate level phosphorylation: phosphate group is transferred from metabolite directly onto ADP o Oxidative phosphorylation: ADP + P -i---ATP Reaction 8 o 3PG ---- 2PG, enzyme is PGM o At the active site, phosphohistidine. Absolutely required for activity o Phosphohistidine attacked by deprotonated 2’-OH o Histidine attacks 3’-PO and 3’-O deprotonates and + 3 acid (B-H ) nd o 2 step is the rate-limiting step o Intermediate (2,3-BPG) just hangs out in active site for a while, sometimes it dissociates from the enzyme o Cannot synthesize phosphohistidine complex o Red Blood Cells harness 2,3-BPG to lower the affinity for O2 – regulator of hemoglobin (alloste

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Chapter 23, Problem 23.47 is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 7
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
ISBN: 9781133952848

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Solved: Show how to bring about each step in the following synthesis