Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card
11th Edition
ISBN: 9781305705159
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 20, Problem 20.82P
Interpretation Introduction
Interpretation:
The transformation of dihydroxyacetone phosphate to D-glyceraldehyde
Concept Introduction:
The process of breakdown of glucose to form pyruvate along with the production of
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
One pathway for the metabolism of D-glucose 6-phosphate is its enzyme-catalyzed
conversion to D-fructose 6-phosphate. Show that this transformation can be accom-
plished as two enzyme-catalyzed keto-enol tautomerisms.
СНО
CH,OH
C=0
enzyme
catalysis
Но
Но
H
OH
H
H.
O-
H-
-HO-
ČH,OPO,
ČH,OPO,
D-Glucose 6-phosphate
D-Fructose 6-phosphate
One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate,
reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH.
-OPO3²- Enz-SH
H-C-OH
ATP
CH₂OPO3²-
3-phosphoglycerate
O
0-0--0
O
ADP
CH₂CH3
substitute for
1,3-bisphosphoglycerate
C
H-C-OH
CH₂OPO3²-
1,3-bisphosphoglycerate
O=C
CH3-SH
substitute for
Enz-SH
H
H-C-OH
|
CH₂OPO3²-
PO4³-
O.
S-Enz
H-C-OH
glyceraldehyde 3-phosphate
Propose a structure for the first intermediates in the reaction of 1,3-bisphosphoglycerate with a thiol group on the enzyme to form an enzyme-bound thioester. Assume a basic group on the enzyme catalyzes the formation of this
intermediate.
To simplify the drawing process, substitute the structures below for the 1,3-bisphosphoglycerate and Enz-SH.
CH₂OPO3²-
(Enzyme-bound
thioester)
NADH/H*
NAD*,…
In the biosynthesis of aromatic amino acids, erythrose-4-phosphate undergoes electrophilic addition to
phosphoenolpyruvate (PEP). Draw the products of this step, paying particular attention to regiochemistry.
ОН
OPOH
ОН
?
Enzyme
Erythrose 4-phosphate
Phosphoenolpyruvate
(PEP)
Chapter 20 Solutions
Bundle: Introduction to General, Organic and Biochemistry, 11th + OWLv2, 4 terms (24 months) Printed Access Card
Ch. 20.1 - Prob. 20.1PCh. 20.2 - Prob. 20.2PCh. 20.2 - Prob. 20.3PCh. 20.3 - Prob. 20.4PCh. 20.4 - Prob. 20.5PCh. 20 - Prob. 20.6PCh. 20 - Prob. 20.7PCh. 20 - Prob. 20.8PCh. 20 - Prob. 20.9PCh. 20 - Prob. 20.10P
Ch. 20 - Prob. 20.11PCh. 20 - Prob. 20.12PCh. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - Prob. 20.15PCh. 20 - Prob. 20.16PCh. 20 - Prob. 20.17PCh. 20 - Prob. 20.18PCh. 20 - .19 What is an amino sugar? Name the three amino...Ch. 20 - Prob. 20.20PCh. 20 - Prob. 20.21PCh. 20 - Prob. 20.22PCh. 20 - Prob. 20.23PCh. 20 - Prob. 20.24PCh. 20 - Prob. 20.25PCh. 20 - Prob. 20.26PCh. 20 - Prob. 20.27PCh. 20 - Prob. 20.28PCh. 20 - Prob. 20.29PCh. 20 - Prob. 20.30PCh. 20 - Prob. 20.31PCh. 20 - Prob. 20.32PCh. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - Prob. 20.35PCh. 20 - Prob. 20.36PCh. 20 - Prob. 20.37PCh. 20 - Prob. 20.38PCh. 20 - Prob. 20.39PCh. 20 - Prob. 20.40PCh. 20 - Prob. 20.41PCh. 20 - Prob. 20.42PCh. 20 - Prob. 20.43PCh. 20 - Prob. 20.44PCh. 20 - Prob. 20.45PCh. 20 - 6 Where is glycogen stored in the human body?Ch. 20 - Prob. 20.47PCh. 20 - 8 How is it possible that cows can digest grass...Ch. 20 - Prob. 20.49PCh. 20 - Prob. 20.50PCh. 20 - 1 Hyaluronic acid acts as a lubricant in the...Ch. 20 - 2 The anticlotting property of heparin is partly...Ch. 20 - Prob. 20.53PCh. 20 - Prob. 20.54PCh. 20 - Prob. 20.55PCh. 20 - Prob. 20.56PCh. 20 - Prob. 20.57PCh. 20 - Prob. 20.58PCh. 20 - Prob. 20.59PCh. 20 - Prob. 20.60PCh. 20 - Prob. 20.61PCh. 20 - 2 In making candy or sugar syrups, sucrose is...Ch. 20 - Prob. 20.63PCh. 20 - Prob. 20.64PCh. 20 - Prob. 20.65PCh. 20 - Prob. 20.66PCh. 20 - Prob. 20.67PCh. 20 - Prob. 20.68PCh. 20 - Prob. 20.69PCh. 20 - 0 What are the structural differences between...Ch. 20 - Prob. 20.71PCh. 20 - Prob. 20.72PCh. 20 - Prob. 20.73PCh. 20 - Prob. 20.74PCh. 20 - Prob. 20.75PCh. 20 - Prob. 20.76PCh. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - Prob. 20.79PCh. 20 - Prob. 20.80PCh. 20 - Prob. 20.81PCh. 20 - Prob. 20.82PCh. 20 - Prob. 20.83PCh. 20 - Prob. 20.84PCh. 20 - Prob. 20.85PCh. 20 - Prob. 20.86PCh. 20 - Prob. 20.87PCh. 20 - Prob. 20.88PCh. 20 - Prob. 20.89P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- rivatives: Nucleophilic Acyl Substitution Reactions - EOC O C-O [References] One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate, reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH. H-C-OH ATP ADP CH₂OPO32- 3-phosphoglycerate 0= OPO32- C H-C-OH CH₂OPO32 1,3-bisphosphoglycerate Enz-SH PO43- O= C S-Enz H-C-OH CH₂OPO3² (Enzyme-bound thioester) NADH/H+ O=C NAD*, Enz-SH H H-C-OH CH₂OPO3²- glyceraldehyde 3-phosphate Propose a structure for the first intermediate in the reaction of the enzyme-bound thioester with NADH to form glyceraldehyde 3-phosphate. To simplify the drawing process, substitute the structure below for the enzyme-bound thioester. S-CH3 substitute for the CH2CH3 enzyme-bound thioester You do not have to consider stereochemistry. • You do not have…arrow_forwardThe first step in the catabolism of most amino acids is the removal of the nitrogen atom by transfer to an a-keto acid, a reaction catalyzed by an enzyme called a transaminase. The a-keto acid acceptor is often a-ketoglutarate. Modify the structures in the product to show the products of the transamination of cysteine. Be sure to show functional groups with the charge and number of attached hydrogen atoms appropriate for pH 7.4. transaminase + O=C H₂N-CH + CH₂ CH₂ CH₂ SH Incorrect H₂N || CH | CH₂ | CH₂ I || O || n | CH₂ T SHarrow_forwardYou do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. Draw phosphate groups, when present, as in the question: in basic form and with a phosphorous oxygen double bond.arrow_forward
- H CH3 H₂C-N-CH₂-C-CH₂- CH3 OH The reason that this compound is required in the diet of humans is that it: O is part of the coenzyme A molecule. O helps fatty acids cross the inner mitochondrial membrane. O is involved in the reoxidation of cytosolic NADH under anaerobic conditions. O is a precursor of one of the most important oxidizing agents in cells. O is part of the flavin adenine dinucleotide molecule. EESarrow_forward5)A certain aerobic organism is able to metabolize the followingglycolipid CH,OH H H OH H HO OH A.Draw the 2 resulting structures that would occur upon initial hydrolysis of the O-glycosidic bond.arrow_forwardGive the major organic product that is formed when the primary hydroxyl group of the following monosaccharide undergo nucleophilic substitution reaction with acetic anhydridearrow_forward
- One of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of sedoheptulose 7-phosphate with glyceraldehydes 3-phosphate in the presence of a transaldolase to yield erythrose 4-phosphate and fructose 6-phosphate. (a) The first part of the reaction is the formation of a protonated Schiff base of sedoheptulose 7-phosphate with a lysine residue in the enzyme followed by a retro-aldol cleavage to give an enamine plus erythrose 4-phosphate. Show the structure of the enamine and the mechanism by which it is formed. (b) The second part of the reaction is a nucleophilic addition of the enamine to glyceraldehyde 3-phosphate followed by hydrolysis of the Schiff base to give fructose 6-phosphate. Show the mechanism.arrow_forwardLinoleic acid is shown below. What makes this fatty acid particularly susceptible to autoxidation? 1. The red CH bond has a low bond dissociation energy because it is doubly allylic. 2. The red CH bond has a high bond dissociation energy because it is doubly allylic. 3. The red CH bond is the most accessible to reaction with O2 because it is the least sterically crowded CH bond. 4. Both 2 and 3.arrow_forwardRaloxifene is a drug used in the treatment of osteoporosis in postmenopausal women and those on glucocorticoids. In a study conducted by Izgelov et al. (2018), the two metabolites derived from raloxifene are shown and their intestinal metabolism are discussed. он Raloxifene 6-Glucuronide HO Raloxifene onge HQ. OH OH OH Raloxifene 4'-Glucuronide Determine the isomer configuration of the labelled double bond (shown in red) from the structure of raloxifene by writing the letter of the configuration in the provided box below. STRICTLY write the letter only.arrow_forward
- How many glycosidic bonds does the following molecule have?arrow_forward2. The following diagram shows the straight-chain structure of an N-acetyl aminoheptose that is found in certain plants including avocado (Persea Americana). CHOH CH2OH CH,OH O: O: HO- но -HO- HO H но -HO- H- NHAC NHAC ACHN OH HN H- HO- HO CH2OH CHOH CH20H HO HO. Structure B Structure C Structure A OH OH CHOH CH2OH CH OH HO H HO H HO- H OH HO- HO H- -NHAC ACHN- ACHN HO- H OH HO ČHOH CH2OH CH2OH Structure D Structure E Structure F Which of the Fischer projections (A-F) matches the skeletal formula shown? Structure A Structure B Structure C Structure D Structure E O Structure F (1 mark) 王 HIarrow_forwardFrom the wedge and dash projection below, which of the following is a (S)- configuration of the glyceraldehyde. * H OH H СНО "СНО OH CHO CH,OH B OH CHO HOH,C H HOH,C HO CH OH A C D O D O B O Aarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning