Interpretation:
The Strecker synthesis of DL-phenylalanine is to be outlined, and by preparing the starting
Concept introduction:
舧 Amino acids are organic compounds containing
舧 Strecker synthesis involves treating an aldehyde with ammonia and hydrogen cyanide to give an aminonitrile, which can be hydrolyzed to an αa-amino acid.
The general reaction is as:
舧 The Strecker synthesis involves formation of imine from phenyl acetaldehyde and ammonia, which on addition of hydrogen cyanide produces
舧 Acrolein and methanethiol on treating with a base gives
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Organic Chemistry, 12e Study Guide/Student Solutions Manual
- -Amino acids can be prepared by the Strecker synthesis, a two-step process in which an aldehyde is treated with ammonium cyanide followed by hydrolysis of the amino nitrile intermediate with aqueous acid. Propose a mechanism for the reaction.arrow_forwardGive the structure of compound A.arrow_forwardShow how you could us the acetamidomalonate method to prepare the followig amino acids (a)Leucine (b)Tryptophanarrow_forward
- 23.1(b,d and e)arrow_forwardWrite out the steps needed to synthesize the following peptide using the Merrifield method.arrow_forwardHistamine is synthesized from one of the 20 protein-derived amino acids. Suggest which amino acid is its biochemical precursor and the type of organic reaction(s) involved in its biosynthesis (e.g., oxidation, reduction, decarboxylation, nucleophilic substitution). CH,CH,NH, H. Histaminearrow_forward
- 22.46 (a&d only)arrow_forwardSuggest a scheme you will follow to synthesise the dipeptide Ala-Glyarrow_forwardAn unknown decapeptide was isolated and characterized. Complete hydrolysis of this peptide gave : F(2), A,G,C,K,N,T, W and V. Treatment with carboxypeptidase releases A. Reaction with Edman’s reagent gave PTH-T and a nonapeptide. The nonapeptide was treated with trypsin and gave 2 peptides: (V-C-G-A) and (N-FF-W-K). Give the sequence of amino acid in the decapeptide.arrow_forward
- Bradykinin is a linear nonapeptide released by blood plasma globulin in response to a wasp sting. It is a very potent pain-causing agent. Its constituent amino acids are 2R, G, 2F, 3P, S. The sue of 2,4-dinitrofluorobenzene and carboxypeptidase shows that both terminal residues are arginine. Partial hydrolysis of bradykinin gives the following di- and tripeptides: FS + PGF +PP + SPF + FR + RParrow_forwardFor each amino acid listed, tell whether its influence on tertiary structure is largely through hydrophobic interactions,hydrogen bonding, formation of salt bridges, covalent bonding, or some combination of these effects.(a) Tyrosine (b) Cysteine(c) Asparagine (d) Lysine(e) Tryptophan (f) Alanine(g) Leucine (h) Methioninearrow_forwardPropose a mechanism for the rearrangement of the thiazoline obtained from the reaction of Edman’s reagent with a peptide to a PTH-amino acidarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning