Concept explainers
17-54 Following is the structure of immunosuppressant FK-506, a molecule shown to disrupt calcineurin-mediated signal transduction in T-lymphocytes.
(a) There are three carbon—carbon double bonds present in this molecule. Which of the three has the potential for cis/trans isomerism? Assign a cis or trans con?guration to each carbon-carbon double bond that has this possibility.
(b) How many stereocenters are present in this molecule? How many stereoisomers are possible for it?
(c) Are there any aromatic components in this molecule?
(d) Consider the two carbon atoms marked with asterisks. Assign an R or S con?guration of each stereocenter.
(e) Because of the presence of a 21-member ring, this molecule is described as a macrocycle. This ring is fashioned by three types of bonds, several carbon-carbon bonds, one ester, one hemiacetal, and one amide. Locate the ester and the hemiacetal.
(f) Draw the structural formula of the long chain compound that would result if the hemiacetal were to be cleaved to an alcohol and a carbonyl group.
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Chapter 17 Solutions
Introduction to General, Organic and Biochemistry
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- 11-58 (Chemical Connections 11A) How many rings in te trodotoxin contain only carbon atoms? How many contain nitrogen atoms? How many contain two oxygen atoms?arrow_forward13-38 (Chemical Connections 13A) What is meant by the term biodegradable?arrow_forward13-39 (Chemical Connections 13B) What is a carcinogen What kind of carcinogen is found in cigarette smoke?arrow_forward
- 11-63 (Chemical Connections 11C) In what way do Fre- ons negatively affect the environment?arrow_forward13-31 What structural features are common to vitamin E, BHT, and BHA (the three antioxidants presented in Section 13-40?arrow_forward13-52 2,6-Di-/ezY-butyl-4-methylphenol (BHT, Section 13-4C) is an antioxidant added to processed foods to “retard spoilage.” How does BHT accomplish this goal?arrow_forward
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