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Give the amino acid sequence of an octapeptide that contains the amino acids Tyr, Ala, Leu (2 equiv), Cys, Gly, Glu and Val, and forms the following fragments when partially hydrolyzed with HCl: Val-Cys-Gly-Glu, Ala-Leu-Tyr, and Tyr-Leu-Val-Cys.

Short Answer

Expert verified

The amino acid sequence of an octapeptide is,

Step by step solution

01

Partial hydrolysis of a peptide

Partial hydrolysis of a peptide is done by treating the peptide with acid, this produces small fragments by identifying the sites for overlap.The common amino acids from the fragments are considered as one amino acid.

02

Amino acid sequence of an octapeptide

First of all, look at the points of overlap in the smaller fragments and how they are placed together. Here, Tyr-Leu-Val-Cys have Tyr common to Ala-Leu-Tyr and Val-Cys common to Val-Cys-Gly-Glu.

These three fragments are joined together by taking common amino acids as one.

Partial hydrolysis with HCl

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Most popular questions from this chapter

Another method to form a peptide bond involves a two-step process:

[1] Conversion of a Boc-protected amino acid to a p-nitrophenyl ester.

[2] Reaction of the p-nitrophenyl ester with an amino acid ester.

  1. Why does a p-nitrophenyl ester 鈥渁ctivate鈥 the carboxy group of the first amino acid to amide formation?

  2. Would a p-methoxyphenyl ester perform the same function? Why or why not?

As shown in Mechanism 29.2, the final steps in the Edman degradation result in rearrangement of a thiazolinone to an N-phenylthiohydantoin. Draw a stepwise mechanism for this acid-catalyzed reaction.

Consider the decapeptide angiotensin I.

  1. What products are formed when angiotensin I is treated with trypsin?
  2. What products are formed when angiotensin I is treated with chymotrypsin?
  1. Treatment of angiotensin I with ACE (the angiotensin-converting enzyme) cleaves only the amide bond with the carbonyl group derived from phenylalanine to afford two products.

The larger polypeptide is angiotensin II, a hormone that narrows blood vessels and increases blood pressure. Give the amino acid sequence of angiotensin II using threeletter abbreviations. ACE inhibitors are drugs that lower blood pressure by inhibiting the ACE enzyme (Problem 5.15).

Draw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr鈥揋ly鈥揋ly鈥揚he鈥揕eu. (The structure of a related peptide, met-enkephalin,

appeared in Section 22.6B.)

What steps are needed to convert A to L-dopa, an uncommon amino acid that is effective in treating Parkinson鈥檚 disease? These steps are the key reactions in the first commercial asymmetric synthesis using a chiral transition metal catalyst. This process was developed at Monsanto in 1974.

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