6. Celiac disease is a disorder of the small intestine characterized by autoimmune response to gluten, a complex of proteins commonly found in wheat and other grains. Gluten proteins contain Gln- and Pro-rich sequences that are resistant to degradation by digestive proteases such as pepsin, trypsin, and chymotrypsin. Recently, enzyme supplements have been proposed as a potential therapy for patients suffering from this disease. One example of these supplements is a cysteine protease that cleaves polypeptide chains on the C-terminal side of Gln residues. Interestingly, the active site contains a catalytic triad of Asp, His, and Cys instead of the expected catalytic dyad. Propose a complete curved-arrow mechanism for the proteolytic cleavage of the gluten peptide segment shown below by the enzyme mentioned above. H. R' `NH2 gluten peptide segment

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
Question
4
6. Celiac disease is a disorder of the small intestine characterized by autoimmune response to gluten, a complex
of proteins commonly found in wheat and other grains. Gluten proteins contain Gln- and Pro-rich sequences that are
resistant to degradation by digestive proteases such as pepsin, trypsin, and chymotrypsin. Recently, enzyme
supplements have been proposed as a potential therapy for patients suffering from this disease. One example of
these supplements is a cysteine protease that cleaves polypeptide chains on the C-terminal side of Gln residues.
Interestingly, the active site contains a catalytic triad of Asp, His, and Cys instead of the expected catalytic dyad.
Propose a complete curved-arrow mechanism for the proteolytic cleavage of the gluten peptide segment shown
below by the enzyme mentioned above.
R'
`NH2
gluten peptide segment
Transcribed Image Text:6. Celiac disease is a disorder of the small intestine characterized by autoimmune response to gluten, a complex of proteins commonly found in wheat and other grains. Gluten proteins contain Gln- and Pro-rich sequences that are resistant to degradation by digestive proteases such as pepsin, trypsin, and chymotrypsin. Recently, enzyme supplements have been proposed as a potential therapy for patients suffering from this disease. One example of these supplements is a cysteine protease that cleaves polypeptide chains on the C-terminal side of Gln residues. Interestingly, the active site contains a catalytic triad of Asp, His, and Cys instead of the expected catalytic dyad. Propose a complete curved-arrow mechanism for the proteolytic cleavage of the gluten peptide segment shown below by the enzyme mentioned above. R' `NH2 gluten peptide segment
Expert Solution
steps

Step by step

Solved in 4 steps with 4 images

Blurred answer
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