Nama : Bella Permatasari

NIM : 4311420043
Mata Kuliah : Makromolekul Kimia

1. Sebutkan, tuliskan struktur, dan klasifisikanlah asam-asam amino sebagai non polar,
polar asam, polar basa, atau polar netral serta beri nama lengkap, tiga singkatan dan
satu singkatannya!.
2. (a) Which amino acids have more than one chirality center?
(b) Write Fischer projections for the isomers of each of these amino acids that would have
the L configuration at the a carbon.
(c) What kind of isomers have you drawn in each case?
 c. Dalam struktur cystine kedua pusat stereo hadir sebagai atom karbon alfa.
Proyeksi fischer untuk isomer masing-masing asam amino ini yang memiliki
konfigurasi L pada karbon alfa tidak mungkin. Oleh karena itu tidak ada isomer
jenis ini yang dapat ditulis

Jenis isomer yang ditarik dalam setiap kasus adalah diastereomer, stereo-isomer
memiliki atom-atomnya yang terhubung dalam urutan yang sama (konstituasi yang
sama), tetapi mereka berbeda dalam susunan atomnya di ruang angkasa. Stereo-
isomer dapat dibagi menjadi dua kategori:
Enansiomer: Enansiomer adalah isomer stereo yang molekulnya merupakan
bayangan cermin yang tidak dapat disuperposisikan satu sama lain.
Diastereomer: Diastereomer adalah isomer stereo yang molekulnya bukan
bayangan cermin satu sama lain.

3. Write the most stable structural formula for tyrosine:

(a) In its cationic form
(b) In its zwitterionic form
(c) As a monoanion
(d) As a dianion
4. Write structural formulas for the principal species present when the pH of a solution
containing lysine is raised from 1 to 9 and again to 13.
Untuk asam amino dengan rantai samping basa, pH(I) dihitung dengan rata-rata pKa2 dan
pKa3
pKa1 = 1,88
pKa2 = 8,95
pKa3 = 10,53
pH (I) = (pKa2 + pKa3)/2
= (8,95 + 10,53)/2 = 19,48/2 = 9,74
Pada nilai pH kurang dari pKa1, spesies utama yang ada adalah

Pada nilai pH antara pKa1 dan pKa2 spesises utamanya adalah zwitterion
Konsentrasi maksimum zwitterion pada titik isoelektrik (pI) = 9,74. Jika nilai pH antara pKa2
dengan pKa3, spesies utamanya adalah

Jika nilai pH lebih dari pKa2, spesies utamanya adalah

5. (a) Write structural formulas showing the constitution of each of the following dipeptides.
Rewrite each sequence using one-letter abbreviations for the amino acids.
(a) Gly-Ala

(b) Ala-Phe

(c) Phe-Ala
(d) Gly-Glu

(e) Lys-Gly

(f) D-Ala-D-Ala

D-Ala D-Ala D-Ala-D-Ala

(b) Expand your answer to Problem 5 (a) by showing the structural formula for each
dipeptide in a manner that reveals the stereochemistry at the α carbon atom.
(a) Gly-Ala
 Glysylalanine (C5H10N2O3)

(b) Ala-Phe
Alanylphenylalanine (C12H16N2O3)

(c) Phe-Ala
Phenylalanylalanine (C12H16N2O3)

(d) Gly-Glu
Glycylglutamic Acid

(e) Lys-Gly
(f) D-Ala-D-Ala
D-Alanyl-D-Alanine(C6H12N2O3)

6. (a) Isoleucine has been prepared by the following sequence of reactions. Give the structure
of compounds A through D isolated as intermediates in this synthesis.
Jawab :

(b) An analogous procedure has been used to prepare phenylalanine. What alkyl halide
would you choose as the starting material for this synthesis?
Jawab :

7. Somatostatin is a tetradecapeptide of the hypothalamus that inhibits the release of pituitary

growth hormone. Its amino acid sequence has been determined by a combination of Edman
degradations and enzymic hydrolysis experiments. On the basis of the following data,
deduce the primary structure of somatostatin:
1. Edman degradation gave PTH-Ala.
2. Selective hydrolysis gave peptides having the following indicated sequences:
Phe-Trp
Thr-Ser-Cys
Lys-Thr-Phe
Thr-Phe-Thr-Ser-Cys
Asn-Phe-Phe-Trp-Lys
Ala-Gly-Cys-Lys-Asn-Phe
3. Somatostatin has a disulfide bridge.
Jawab :
8. Complete hydrolysis of a heptapeptide showed that it has the following constituent amino
acids: 2A, E, L, K, F, V
Deduce the amino acid sequence of this heptapeptide from the following data:
1. Treatment of the heptapeptide with 2,4-dinitrofluorobenzene followed by incomplete
hydrolysis gave, among other products: valine labeled at the α-amino group, lysine
labeled at the ε-amino group, and a dipeptide,
DNP VL (DNP–2,4-dinitrophenyl-).
2. Hydrolysis of the heptapeptide with carboxypeptidase gave an initial high concentration
of alanine, followed by a rising concentration of glutamic acid.
3. Partial enzymatic hydrolysis of the heptapeptide gave a dipeptide (A) and a tripeptide
(B).
a. Treatment of A with 2,4-dinitrofluorobenzene followed by hydrolysis gave DNP-
labeled leucine and lysine labeled only at the ε -amino group.
b. Complete hydrolysis of B gave phenylalanine, glutamic acid, and alanine. When B was
allowed to react with carboxypeptidase, the solution showed an initial high
concentration of glutamic acid. Treatment of B with 2,4-dinitrofluorobenzene
followed by hydrolysis gave labeled phenylalanine.
Jawab :

A → satu kode huruf untuk Alanine

E → satu kode huruf untuk Glutamic acid
L → satu kode huruf untuk Lencine
K → satu kode huruf untuk Lysine
F → satu kode huruf untuk Phenylalanine
V → satu kode huruf untuk Valine

1). 2,4-dinitrofluorobenzene adalah reagen sanger yang digunakan untuk

mengidentifikasi terminal amino polipeptida
2). carboxypeptidase memotong ikatan peptida dari terminal karboksi
3). Partial enzymatic hydrolysis of the heptapeptide gave a dipeptide (A) and a tripeptide (B).

dengan demikian, urutan lengkapnya adalah :

Amino terminus Carboxy terminus
Valine - Leucine – Lysine – Phenylalanine – Alanine - Glutamic Acid - Alanine
(V) (L) (K) (F) (A) (E) (A)
(V,L,K,F,A,E,A)