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Chemistry 0740 Chapter 21: Understanding the Role of Cofactors in Organic Reactions, Study notes of Chemistry

University of Pittsburgh (Pitt) - Medical Center-Health SystemChemistry

A chapter from an organic chemistry course focusing on the role of cofactors, also known as co-enzymes, in biological reactions. The chapter covers the mechanisms of various cofactor-dependent reactions, including those involving pap, plp, tpp, fad, fadh, sam, and nad+/nadh. Students are expected to be able to draw mechanisms for these reactions and recognize the unique rearrangements catalyzed by certain cofactors. The document also includes learning objectives, chapter advice, and handouts.

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COURSES > 2081_10353 - CHEM 0320: ORGANIC CHEMISTRY 2 > COURSE D OCUMENTS > CHEM 0740 CHAPTER 21. COFACTORS FOR BIOLOGICAL
REACTIONS EDIT VIEW
Chem 0740 Chapter 21. Cofactors for Biological Reactions
Last Updated: 10 April 2007
Chapter 21. Cofactors for Biological Reactions
Introduction
In this chapter, we will focus on understanding the "chemistry" (i.e., the bond-making and bond-
breaking) of several of the enzymatic cofactors (co-enzymes) that are listed on the side of the cereal
boxes. Several of the compounds are also known to be vitamins. As you work your way through the
material (much of it will come from the lecture rather than the book) keep in mind that all the
microscopic steps of every reaction follow the basic principles that we have developed over the past
year, including: each and every step must be mass- and charge-balanced, acidities of proton donors
and conjugate acids of proton bases must allow the proton transfer envsioned, nucleophiles attack
electrophiles, and electrophiles are often activated prior to undergoing reaction. Even though the
substrates have become more complicated, the actual reactions and mechanisms are no-more
complicated than reactions we have so far discussed.
Learning Objectives
(1) Be able to draw mechanisms for PAP and PLP-dependent reactions.
(2) Be able to draw mechanisms for TPP-dependent reactions.
(3) Be able to draw mechanisms for FAD and FADH-dependent reactions.
(4) Be able to draw mechanism for SAM and NAD+/NADH-dependent reactions.
(5) Be able to recognize the unique rearrangements catalyzed by coenzyme-B12.
(6) Be able to specify which cofactors are likely to be involved for any metabolic or catabolic reaction.
Chapter Advice
As you read this chapter, always keep in mind the fundamental organic chemistry principles that we
have developed throughout the course, and make sure those principles are still followed! Don't let the
much larger structures now involved in the "catalysis" distract you from the important issues (which
are bond-breaking and bond-making).
Handouts
Click here to receive the lecture notes, in pdf format, 4 slides/page. (688.107 Kb)
Molecules
Exercises
Fox & Whitesell, Chapter 21: #1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, and 17.

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COURSES > 2081_10353 - CHEM 0320: ORGANIC CHEMISTRY 2 > COURSE DOCUMENTS > CHEM 0740 CHAPTER 21. COFACTORS FOR BIOLOGICAL REACTIONS EDIT VIEW

Chem 0740 Chapter 21. Cofactors for Biological Reactions

Last Updated: 10 April 2007 Chapter 21. Cofactors for Biological Reactions

Introduction In this chapter, we will focus on understanding the "chemistry" (i.e., the bond-making and bond- breaking) of several of the enzymatic cofactors (co-enzymes) that are listed on the side of the cereal boxes. Several of the compounds are also known to be vitamins. As you work your way through the material (much of it will come from the lecture rather than the book) keep in mind that all the microscopic steps of every reaction follow the basic principles that we have developed over the past year, including: each and every step must be mass- and charge-balanced, acidities of proton donors and conjugate acids of proton bases must allow the proton transfer envsioned, nucleophiles attack electrophiles, and electrophiles are often activated prior to undergoing reaction. Even though the substrates have become more complicated, the actual reactions and mechanisms are no-more complicated than reactions we have so far discussed.

Learning Objectives (1) Be able to draw mechanisms for PAP and PLP-dependent reactions. (2) Be able to draw mechanisms for TPP-dependent reactions. (3) Be able to draw mechanisms for FAD and FADH-dependent reactions. (4) Be able to draw mechanism for SAM and NAD+/NADH-dependent reactions. (5) Be able to recognize the unique rearrangements catalyzed by coenzyme-B12. (6) Be able to specify which cofactors are likely to be involved for any metabolic or catabolic reaction.

Chapter Advice As you read this chapter, always keep in mind the fundamental organic chemistry principles that we have developed throughout the course, and make sure those principles are still followed! Don't let the much larger structures now involved in the "catalysis" distract you from the important issues (which are bond-breaking and bond-making).

Handouts Click here to receive the lecture notes, in pdf format, 4 slides/page. (688.107 Kb)

Molecules

Exercises Fox & Whitesell, Chapter 21: #1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, and 17.