b) Some peptides bear an interesting modification to their primary structure. In these peptides, the C-terminal residue is converted from a carboxylate to a primary amide. This is typically signified by appending "-NH," to the three- letter abbreviation of that residue. With this information in mind, draw the structure of the cyclic peptide below, being sure to account for this modification as well as correct stereochemistry and charges at pH 7.4. (Also note well the presence of the disulfide bond in this peptide!) The N-terminus of this peptide is indicated explicitly to help guide you. H3N Cys-Tyr N-terminus lle S. Gin Cys-Asn H2N-GlyArg-Pro c) The primary amide modification of terminal amino acid residues in peptides (as in Gly above) is found to increase their conformational stability over a relatively wide pH range. Provide a brief explanation as to why this might be the case.

Biochemistry
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Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
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Chapter1: Biochemistry: An Evolving Science
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b) Some peptides bear an interesting modification to their primary structure. In these peptides, the C-terminal residue
is converted from a carboxylate to a primary amide. This is typically signified by appending "-NH2" to the three-
letter abbreviation of that residue. With this information in mind, draw the structure of the cyclic peptide below,
being sure to account for this modification as well as correct stereochemistry and charges at pH 7.4. (Also note well
the presence of the disulfide bond in this peptide!) The N-terminus of this peptide is indicated explicitly to help
guide you.
N-terminus
Cys-Tyr
lle
Gln
Cys-Asn
H2N-Gly-Arg-Pro
c) The primary amide modification of terminal amino acid residues in peptides (as in Gly above) is found to increase
their conformational stability over a relatively wide pH range. Provide a brief explanation as to why this might be
the case.
Transcribed Image Text:b) Some peptides bear an interesting modification to their primary structure. In these peptides, the C-terminal residue is converted from a carboxylate to a primary amide. This is typically signified by appending "-NH2" to the three- letter abbreviation of that residue. With this information in mind, draw the structure of the cyclic peptide below, being sure to account for this modification as well as correct stereochemistry and charges at pH 7.4. (Also note well the presence of the disulfide bond in this peptide!) The N-terminus of this peptide is indicated explicitly to help guide you. N-terminus Cys-Tyr lle Gln Cys-Asn H2N-Gly-Arg-Pro c) The primary amide modification of terminal amino acid residues in peptides (as in Gly above) is found to increase their conformational stability over a relatively wide pH range. Provide a brief explanation as to why this might be the case.
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