Part [1] Formation of an N-phenylthiourea CHs PEPTIDE PEPTIDE PEPTIDE CH, CHs R. 'R phenyl isothiocyanate нн N-phenylthiourea 1-2 Addition of the amino group of the N-terminal amino acid to phenyl isothiocyanate followed by proton transfer forms an N-phenylthiourea. Part [2] Formation of the N-terminal amino acid and N-phenylthiohydantoin (PTH) н-А HÖ PEPTIDE several CeHs. steps PEPTIDE -H* N. Н-А -R CeHs CeHs CHs 'R N-phenylthiourea thiazolinone N-phenylthiohydantoin (PTH) HạN- PEPTIDE 3 Nucleophilic addition of the S atom to the amide carbonyl forms a five-membered ring. 4 Loss of the amino group forms two products-a thiazolinone ring and a peptide chain that contains one fewer amino acid than the original peptide. 5 The thiazolinone rearranges by a multistep pathway to form an N-phenylthiohydantoin (PTH) that contains the original amino acid.
Part [1] Formation of an N-phenylthiourea CHs PEPTIDE PEPTIDE PEPTIDE CH, CHs R. 'R phenyl isothiocyanate нн N-phenylthiourea 1-2 Addition of the amino group of the N-terminal amino acid to phenyl isothiocyanate followed by proton transfer forms an N-phenylthiourea. Part [2] Formation of the N-terminal amino acid and N-phenylthiohydantoin (PTH) н-А HÖ PEPTIDE several CeHs. steps PEPTIDE -H* N. Н-А -R CeHs CeHs CHs 'R N-phenylthiourea thiazolinone N-phenylthiohydantoin (PTH) HạN- PEPTIDE 3 Nucleophilic addition of the S atom to the amide carbonyl forms a five-membered ring. 4 Loss of the amino group forms two products-a thiazolinone ring and a peptide chain that contains one fewer amino acid than the original peptide. 5 The thiazolinone rearranges by a multistep pathway to form an N-phenylthiohydantoin (PTH) that contains the original amino acid.
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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As shown in Mechanism 29.2, the nal steps in the Edman degradation result in rearrangement of a thiazolinone to an Nphenylthiohydantoin. Draw a stepwise mechanism for this acid-catalyzed reaction.
Mechanism 29.2: Edman Degradation
![Part [1] Formation of an N-phenylthiourea
CHs
PEPTIDE
PEPTIDE
PEPTIDE
CH,
CHs
R.
'R
phenyl isothiocyanate
нн
N-phenylthiourea
1-2 Addition of the amino group of the N-terminal amino acid to phenyl isothiocyanate followed by proton transfer forms an
N-phenylthiourea.
Part [2] Formation of the N-terminal amino acid and N-phenylthiohydantoin (PTH)
н-А
HÖ
PEPTIDE
several CeHs.
steps
PEPTIDE
-H*
N.
Н-А
-R
CeHs
CeHs
CHs
'R
N-phenylthiourea
thiazolinone
N-phenylthiohydantoin
(PTH)
HạN- PEPTIDE
3 Nucleophilic addition of the S atom to the amide carbonyl forms a five-membered ring.
4 Loss of the amino group forms two products-a thiazolinone ring and a peptide chain that contains one fewer amino acid
than the original peptide.
5 The thiazolinone rearranges by a multistep pathway to form an N-phenylthiohydantoin (PTH) that contains the original
amino acid.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F14956b9f-b937-429f-be5a-def7941888b1%2F57de5288-1f10-4d13-a44b-14ecacc8ffed%2Fgnoljal.png&w=3840&q=75)
Transcribed Image Text:Part [1] Formation of an N-phenylthiourea
CHs
PEPTIDE
PEPTIDE
PEPTIDE
CH,
CHs
R.
'R
phenyl isothiocyanate
нн
N-phenylthiourea
1-2 Addition of the amino group of the N-terminal amino acid to phenyl isothiocyanate followed by proton transfer forms an
N-phenylthiourea.
Part [2] Formation of the N-terminal amino acid and N-phenylthiohydantoin (PTH)
н-А
HÖ
PEPTIDE
several CeHs.
steps
PEPTIDE
-H*
N.
Н-А
-R
CeHs
CeHs
CHs
'R
N-phenylthiourea
thiazolinone
N-phenylthiohydantoin
(PTH)
HạN- PEPTIDE
3 Nucleophilic addition of the S atom to the amide carbonyl forms a five-membered ring.
4 Loss of the amino group forms two products-a thiazolinone ring and a peptide chain that contains one fewer amino acid
than the original peptide.
5 The thiazolinone rearranges by a multistep pathway to form an N-phenylthiohydantoin (PTH) that contains the original
amino acid.
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