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Question

Aspartame, an artificial sweetener, is a peptide and has the following structure
(I) Identify the four functional groups
(II) Write the zwitter ionic structure
(III) Write the structures of the amino acids obtained from the hydrolysis of aspartame
(IV) Which of the two amino acids is more hydrophobic?
H2NC|CH2COOHHCONHCH2C6H5|CHCOOCH3

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Solution

H2NCH|CH2COOHCONHCH2C6H5|CHCOOCH3

(1) The 4 functional groups are - NH2 (Ammonia)/(Amine)
- CONH (Amide)
- COOH (carboxylic Acid)
- COOCH3 (Either)

(2) Zwitter ionic structure:
⎢ ⎢ ⎢ ⎢H2+NCH|CH2COOCONHCH2C6H5|CHCOOCH3⎥ ⎥ ⎥ ⎥ Zwitter ion is a molocule with functinal groups, of which at least one has a positive and one has a negative electrical change.

(3) Refer image.

(4) Phenylalanine is more hydrophobic because its side chain is highly non-polar w.r.t. to others, so it will repeal water molecular.

1351461_1135419_ans_f2481f2fbd494377bc3b55b12d08a4cf.jpg

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