6. Suppose there is a glycolytic-like pathway carried out by an alien species that uses analogous enyzme mechanisms to convert an 8-carbon sugar (O see structure below) to two 4 carbon fragments and then to a pyruvate analog. Draw the mechanism for the conversion of 8-carbon bisphosphate (compound © below) to the two 4 carbon fragments (compounds O and ©) using the mechanism of fructose-1,6-bisphosphate aldolase (Type I) as your model. You need to include the steps for the formation of the covalent intermediate between the enzyme and the substrate. 2 3 CH2OH CH2OH CH,OH CH2OPO,2- -OH -OH -OH -OH HO- но- но- Но но HO- но- но- -OH -OH -OH -OH -OH -OH -OH- -OH ČH2OH ČH,OPO,2 ČH,OPO,2- ČH,OPO,2- 6 CH2OPO,2- CHO -OH -OH ČH2OH ČH2OPO,2 운 운

Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
icon
Related questions
icon
Concept explainers
Question
**Transcription for Educational Website:**

**Title: Glycolytic-like Pathway in an Alien Species: Conversion of an 8-Carbon Sugar**

**Problem Statement:**
Suppose there is a glycolytic-like pathway carried out by an alien species that utilizes enzyme mechanisms analogous to those found in Earth biology. The process involves converting an 8-carbon sugar (structure 1) to two 4-carbon fragments and subsequently to a pyruvate analog. 

**Objective:**
Using the mechanism of fructose-1,6-bisphosphate aldolase (Type I) as a model, draw and explain the mechanism for the conversion of an 8-carbon bisphosphate (compound ④) into two 4-carbon fragments (compounds ⑤ and ⑥). Detail the formation of the covalent intermediate between the enzyme and substrate. 

**Chemical Structures and Pathway Explanation:**

1. **Structures and Intermediates:**

   - **Compound ①:** An 8-carbon sugar with a structure containing multiple hydroxyl (OH) groups and an aldehyde group at one end.
   - **Compound ② and ③:** Transition states where rearrangements occur in the sugar backbone, with specific orientation changes of OH groups and the introduction of a bisphosphate group attached at one end.
   - **Compound ④:** An 8-carbon bisphosphate, indicating further preparation for cleavage into two 4-carbon entities.

2. **Cleavage to Two 4-carbon Fragments:**
   
   - **Compound ⑤:** A 4-carbon fragment resulting from the cleavage, containing a bisphosphate group, a hydroxyl group, and a carbonyl group structure. 
   - **Compound ⑥:** Another 4-carbon fragment produced alongside compound ⑤, with an aldehyde group at one end, a bisphosphate group, and hydroxyl groups. 

**Mechanism Steps:**

1. **Initial Substrate Binding (Compound ①):**
   - The 8-carbon sugar binds to the enzyme, initiating the reaction.

2. **Formation of Covalent Intermediate (Compounds ② and ③):**
   - A series of rearrangements occur, leading to the formation of a covalent intermediate.
   - Rearrangement of hydroxyl groups and phosphorylation occurs, priming the sugar for cleavage.

3. **Aldolase Catalyzed Cleavage (Compound ④ to ⑤ and
Transcribed Image Text:**Transcription for Educational Website:** **Title: Glycolytic-like Pathway in an Alien Species: Conversion of an 8-Carbon Sugar** **Problem Statement:** Suppose there is a glycolytic-like pathway carried out by an alien species that utilizes enzyme mechanisms analogous to those found in Earth biology. The process involves converting an 8-carbon sugar (structure 1) to two 4-carbon fragments and subsequently to a pyruvate analog. **Objective:** Using the mechanism of fructose-1,6-bisphosphate aldolase (Type I) as a model, draw and explain the mechanism for the conversion of an 8-carbon bisphosphate (compound ④) into two 4-carbon fragments (compounds ⑤ and ⑥). Detail the formation of the covalent intermediate between the enzyme and substrate. **Chemical Structures and Pathway Explanation:** 1. **Structures and Intermediates:** - **Compound ①:** An 8-carbon sugar with a structure containing multiple hydroxyl (OH) groups and an aldehyde group at one end. - **Compound ② and ③:** Transition states where rearrangements occur in the sugar backbone, with specific orientation changes of OH groups and the introduction of a bisphosphate group attached at one end. - **Compound ④:** An 8-carbon bisphosphate, indicating further preparation for cleavage into two 4-carbon entities. 2. **Cleavage to Two 4-carbon Fragments:** - **Compound ⑤:** A 4-carbon fragment resulting from the cleavage, containing a bisphosphate group, a hydroxyl group, and a carbonyl group structure. - **Compound ⑥:** Another 4-carbon fragment produced alongside compound ⑤, with an aldehyde group at one end, a bisphosphate group, and hydroxyl groups. **Mechanism Steps:** 1. **Initial Substrate Binding (Compound ①):** - The 8-carbon sugar binds to the enzyme, initiating the reaction. 2. **Formation of Covalent Intermediate (Compounds ② and ③):** - A series of rearrangements occur, leading to the formation of a covalent intermediate. - Rearrangement of hydroxyl groups and phosphorylation occurs, priming the sugar for cleavage. 3. **Aldolase Catalyzed Cleavage (Compound ④ to ⑤ and
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 1 images

Blurred answer
Knowledge Booster
Metabolic pathways
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, biochemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Biochemistry
Biochemistry
Biochemistry
ISBN:
9781319114671
Author:
Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:
W. H. Freeman
Lehninger Principles of Biochemistry
Lehninger Principles of Biochemistry
Biochemistry
ISBN:
9781464126116
Author:
David L. Nelson, Michael M. Cox
Publisher:
W. H. Freeman
Fundamentals of Biochemistry: Life at the Molecul…
Fundamentals of Biochemistry: Life at the Molecul…
Biochemistry
ISBN:
9781118918401
Author:
Donald Voet, Judith G. Voet, Charlotte W. Pratt
Publisher:
WILEY
Biochemistry
Biochemistry
Biochemistry
ISBN:
9781305961135
Author:
Mary K. Campbell, Shawn O. Farrell, Owen M. McDougal
Publisher:
Cengage Learning
Biochemistry
Biochemistry
Biochemistry
ISBN:
9781305577206
Author:
Reginald H. Garrett, Charles M. Grisham
Publisher:
Cengage Learning
Fundamentals of General, Organic, and Biological …
Fundamentals of General, Organic, and Biological …
Biochemistry
ISBN:
9780134015187
Author:
John E. McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson
Publisher:
PEARSON