Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 24.10B, Problem 24.25P
Show how you would synthesize Leu-Gly-Ala-Val-Phe starting with Fmoc-Ala-Val-Phe—P.
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Show how you would synthesize Leu-Gly-Ala-Val-Phe starting with Fmoc-Ala-Val-Phe— P .P
Show the steps in the synthesis of the tetrapeptide Leu-Phe-Ala-Val.
What is the structure of the N-phenylthiohydantoin (PTH) formed upon treatment of a peptide with an alanine at the
N-terminus upon reaction with N-phenylisothioisocyanate (PITC)?
Ph
-CH
--CH
'N'
PhN=C=S
(PITC)
2
Ph
HCI
H,0
Ala-
peptide
H.
CH
CH
Chapter 24 Solutions
Organic Chemistry (9th Edition)
Ch. 24.2A - Draw three-dimensional representations of the...Ch. 24.2A - Prob. 24.2PCh. 24.2B - The herbicide glyphosate (Roundup) kills plants by...Ch. 24.4 - Draw the structure of the predominant form of a....Ch. 24.4 - Draw the resonance forms of a protonated guanidino...Ch. 24.4 - Although tryptophan contains a heterocyclic amine,...Ch. 24.4 - Prob. 24.7PCh. 24.4 - Prob. 24.8PCh. 24.5A - Show how the following amino acids might be formed...Ch. 24.5B - Prob. 24.10P
Ch. 24.5C - Prob. 24.11PCh. 24.5C - Show how you would use a Strecker synthesis to...Ch. 24.6 - Suggest how you would separate the free i-ammo...Ch. 24.7A - Propose a mechanism for the acid-catalyzed...Ch. 24.7A - Give equations for the formation and...Ch. 24.7B - Prob. 24.16PCh. 24.7C - Prob. 24.17PCh. 24.8B - Draw the complete structures of the following...Ch. 24.9C - Prob. 24.19PCh. 24.9C - Prob. 24.20PCh. 24.9C - Prob. 24.21PCh. 24.9E - Prob. 24.22PCh. 24.9E - Prob. 24.23PCh. 24.10A - Propose a mechanism for the coupling of acetic...Ch. 24.10B - Show how you would synthesize Leu-Gly-Ala-Val-Phe...Ch. 24.10B - Show how solid-phase peptide synthesis would be...Ch. 24 - a. The isoelectric point (pl) of phenylalanine is...Ch. 24 - Prob. 24.28SPCh. 24 - Prob. 24.29SPCh. 24 - Prob. 24.30SPCh. 24 - Prob. 24.31SPCh. 24 - Suggest a method for the synthesis of the...Ch. 24 - Prob. 24.33SPCh. 24 - Write the complete structures for the following...Ch. 24 - The following structure is drawn in an...Ch. 24 - Prob. 24.36SPCh. 24 - Prob. 24.37SPCh. 24 - Show the steps and intermediates in the synthesis...Ch. 24 - Prob. 24.39SPCh. 24 - Lipoic acid is often found near the active sites...Ch. 24 - Prob. 24.41SPCh. 24 - Prob. 24.42SPCh. 24 - Prob. 24.43SPCh. 24 - Complete hydrolysis of an unknown basic...Ch. 24 - Prob. 24.45SPCh. 24 - Prob. 24.46SPCh. 24 - Prob. 24.47SP
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- How many of the -amino acids shown in Table 26-1 contain aromatic rings? How many contain sulfur? How many contain alcohols? How many contain hydrocarbon side chains?arrow_forwardWhich amino acids could be referred to as derivatives of butanoic acid?arrow_forwardPrepare valine from the corresponding: a) aldehyde, b) halocarboxylic acid, c) keto acid, d) nitro acid.arrow_forward
- Draw the structure of the tetrapeptide Asp-Arg-Val-Tyr. Please show the appropriate stereochemistry of the natural amino acids in the resulting peptide. Please draw all ionizable groups in their neutral form.arrow_forwardHow could the sequence of Ala-Met-Thr be distinguished from that of Thr-Ala-Met bytandem ESI-MS? Explain in detail.arrow_forwardA decapeptide has the following amino acid composition. Ala2, Arg, Cys, Glu, Gly, Leu, Lys, Phe, Val Partial hydrolysis yields the following tripeptides. Cys-Glu-Leu + Gly-Arg-Cys + Leu-Ala-Ala + Lys-Val-Phe + Val-Phe-Gly One round of Edman degradation yields a lysine phenylthiohydantoin. From this information, deduce the primary structure of this decapeptide.arrow_forward
- A decapeptide has the following amino acid composition:Ala2 , Arg, Cys, Glu, Gly, Leu, Lys, Phe, ValPartial hydrolysis yields the following tripeptides:Cys-Glu-Leu + Gly-Arg-Cys + Leu-Ala-Ala+ Lys-Val-Phe + Val-Phe-Gly.Reaction of the decapeptide with 2,4-dinitrofluorobenzene yields 2,4-dinitrophenylysine. Fromthe experimental data, suggest a scheme you will follow to synthesize the dipeptide Ala-Glyarrow_forwardFrom the following protected amino acids, write the reaction equation to synthesize a tripeptide of Gly-Ala-Cys using Merrifield Solid Technique. HO NH-Bос OH HS Вос-HN. NH-Boc OH Glycine (Gly) Alanine (Ala) Cystein (Cys)arrow_forwardConsider the following peptide. Assume the following about the peptide: C-terminus, pKa = 2 & N-terminus, pka =9 • Calculate the pl of the peptide. H H-N+ H H O N. H N.+ но H H H I. N. N: H NH -0.arrow_forward
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